Supporting Information Diastereoselective synthesis of CF3 ... · Supporting Information Diastereoselective synthesis of CF3-oxazinoquinolines in water Vasiliy M. Muzalevskiya, Kseniya
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Supporting Information
Diastereoselective synthesis of CF3-oxazinoquinolines in waterVasiliy M. Muzalevskiya, Kseniya V. Belyaevab, Boris A. Trofimov*b, Valentine G. Nenajdenko*a
a M. V. Lomonosov Moscow State University, Department of Chemistry, Leninskie Gory 1, Moscow, 119991 Russian Federation
bA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., Irkutsk, 664033
Russian Federation; Fax: (395-2)41-93-46
Table of contents
General remarks S2
Reaction of CF3-ynones and quinolines in water (general procedure) S2
Characterization data of CF3-oxazinoquinolines 3 S2-S8
Epimerization of (3R*,4aR)-1-phenyl-3-(trifluoromethyl)-3H,4aH-[1,3]oxazino[3,2-a]quinolin-3-ol (3a) S8
1.480=9.86. For multi gram scale reaction (3 equivalents of water): compound 3a was obtained from
quinoline 1a (1.612 g, 12.5 mmol), water (0.675 mL) and acetylene 2a (2.612 g, 13.1 mmol). Ethyl acetate (6
mL) and heptane (20 mL) were used for first crystallization. For purification of material obtained from the
mother liquor ethyl acetate (2.5 mL) and heptane (8 mL) were used. White powder, m.p. 154-156 C
(heptane), yield 3.878 g (90%). Calculation of E-factor for multi gram scale reaction (3 equiv.):
1 V. M. Muzalevskiy, A. Yu. Rulev, A. R. Romanov, E. V. Kondrashov, I. A. Ushakov, V. A. Chertkov and V. G. Nenajdenko, J. Org. Chem., 2017, 82, 7200.2 B. A. Trofimov, K. V. Belyaeva, L. P. Nikitina, A. V. Afonin, A. V. Vashchenko, V. M. Muzalevskiy and V. G. Nenajdenko, Chem. Commun., 2018, 54, 2268.
6…399 (~200-300 mL of eluents was used))/0.148=1983…2867~ 2000-3000.1H NMR (400.13 MHz, CD3CN): δ 7.56-7.54 (m, 2H, Ho from Ph), 7.47-7.39 (m, 3H, Hm,p from Ph), 7.25
129.5, 128.9, 128.2, 127.7, 126.6, 121.0. The NMR data of 2-((4,4,4-trifluoro-3-oxo-1-phenylbut-1-en-1-
yl)thio)acetate 53 and quinoline4 are in agreement with those in the literature.
Transformation of oxazine (3a) into 2-phenylquinoline (6). A 4 mL vial with a screw cap was charged
with oxazine 3a (0.030 g, 0.087 mmol), water (0.5 mL) and NaOH (0.0104 g, 0.261 mmol). The reaction
mixture was heated at 80 C at stirring for 2 h. After cooling down to room temperature, the reaction mixture
was extracted with EtOAc (2x0.5 mL), combined organic phase was passed through a short silica gel pad
3 V. M. Muzalevskiy, A. A. Iskandarov, V. G. Nenajdenko, J. Fluorine Chem. 2018, 214, 13-16.4 T. Kaiya, N. Shiraiy, Y. Kawazoe, Chem. Pharm. Bull., 1986, 34, 881-885.
S9
MeO2C S O
Ph CF3
N
+
using heptane followed by heptane-EtOAc (15:1) as an eluents. Evaporation of volatiles afforded 6 as light
HRMS (ESI-TOF): m/z [M+H]+ Calcd for C20H21F3NO2+: 364.1519; found: 364.1522.
S12
23 Feb 2019
FW 345.3152 Formula C19H14F3NO2
Acquisition Time (sec) 4.0894 Comment Imported from UXNMR. Date 22 Feb 2019 23:06:50File Name C:\BM_DATA\DOCS\Manuscr_Ultra\BM_2018\bm190222\BM-1499_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 8 Original Points Count 32768 Points Count 131072Pulse Sequence zg30 Solvent ACETONITRILE-D3 Sweep Width (Hz) 8012.82Temperature (degree C) 27.000
Acquisition Time (sec) 1.9000 Date Oct 1 2018 File Name C:\DOCS\OUTPUT_301\F19\2018.10.01\BM-1371_20181001_01\FLUORINE_01Frequency (MHz) 376.31 Nucleus 19F Number of Transients 16 Original Points Count 169643Points Count 262144 Pulse Sequence s2pul Solvent DMSO-D6 Sweep Width (Hz) 89285.71Temperature (degree C) 22.000
Acquisition Time (sec) 4.0894 Comment Imported from UXNMR. Date 24 Jul 2019 17:34:04File Name C:\DOCS\OUTPUT_301\2019\07.èþ ëü\190724\BM-1659-1_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 8 Original Points Count 32768 Points Count 131072Pulse Sequence zg30 Solvent CHLOROFORM-D Sweep Width (Hz) 8012.82Temperature (degree C) 27.000
1H NMR spectrum of 3a in multi gram scale synthesis (400.1 MHz, CDCl3)
S15
12 Feb 2019
FW 359.3418 Formula C20H16F3NO2
Acquisition Time (sec) 4.0894 Comment Imported from UXNMR. Date 27 Sep 2018 19:18:46File Name C:\DOCS\OUTPUT_301\2018\09.ñåí òÿáðü\BM-1372\BM-1372_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 8 Original Points Count 32768 Points Count 131072Pulse Sequence zg30 Solvent ACETONITRILE-D3 Sweep Width (Hz) 8012.82Temperature (degree C) 27.000
Acquisition Time (sec) 1.0000 Date Sep 28 2018 File Name C:\DOCS\OUTPUT_301\F19\2018.09.28\BM-1372_20180928_01\FLUORINE_01Frequency (MHz) 376.31 Nucleus 19F Number of Transients 16 Original Points Count 89286Points Count 131072 Pulse Sequence s2pul Solvent ACETONITRILE-D3Sweep Width (Hz) 89285.71 Temperature (degree C) 22.000
Acquisition Time (sec) 4.0894 Comment Imported from UXNMR. Date 17 Oct 2018 23:19:18File Name C:\DOCS\OUTPUT_301\2018\10.î êòÿáðü\bm181017\BM-1397d_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 8 Original Points Count 32768 Points Count 131072Pulse Sequence zg30 Solvent ACETONITRILE-D3 Sweep Width (Hz) 8012.82Temperature (degree C) 27.000
Acquisition Time (sec) 2.3069 Date Oct 18 2018 File Name C:\DOCS\OUTPUT_301\F19\2018.10.18\BM-1397d-F_20181018_01\FLUORINE_01Frequency (MHz) 376.32 Nucleus 19F Number of Transients 8 Original Points Count 262144Points Count 262144 Pulse Sequence s2pul Solvent ACETONITRILE-D3Sweep Width (Hz) 113636.37 Temperature (degree C) 22.000
Acquisition Time (sec) 2.5559 Comment Imported from UXNMR. Date 02 Oct 2018 15:32:08File Name C:\DOCS\OUTPUT_301\2018\10.î êòÿáðü\BM-1377-2.H_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 4 Original Points Count 16384 Points Count 65536Pulse Sequence zg30 Solvent ACETONITRILE-D3 Sweep Width (Hz) 6410.26Temperature (degree C) 27.000
Acquisition Time (sec) 2.3069 Date Oct 4 2018 File Name C:\DOCS\OUTPUT_301\F19\2018.10.04\BM-1377-F_20181004_01\FLUORINE_01Frequency (MHz) 376.32 Nucleus 19F Number of Transients 8 Original Points Count 262144Points Count 262144 Pulse Sequence s2pul Solvent ACETONITRILE-D3Sweep Width (Hz) 113636.37 Temperature (degree C) 22.000
Acquisition Time (sec) 2.5559 Comment Imported from UXNMR. Date 29 Sep 2018 14:08:28File Name C:\DOCS\OUTPUT_301\2018\09.ñåí òÿáðü\BM-1373.H_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 4 Original Points Count 16384 Points Count 65536Pulse Sequence zg30 Solvent ACETONITRILE-D3 Sweep Width (Hz) 6410.26Temperature (degree C) 27.000
Acquisition Time (sec) 1.9000 Date Oct 1 2018 File Name C:\DOCS\OUTPUT_301\F19\2018.10.01\BM-1373_20181001_01\FLUORINE_01Frequency (MHz) 376.31 Nucleus 19F Number of Transients 16 Original Points Count 169643Points Count 262144 Pulse Sequence s2pul Solvent DMSO-D6 Sweep Width (Hz) 89285.71Temperature (degree C) 22.000
Acquisition Time (sec) 2.5559 Comment Imported from UXNMR. Date 02 Oct 2018 15:34:56File Name C:\DOCS\OUTPUT_301\2018\10.î êòÿáðü\BM-1378.H_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 4 Original Points Count 16384 Points Count 65536Pulse Sequence zg30 Solvent ACETONITRILE-D3 Sweep Width (Hz) 6410.26Temperature (degree C) 27.000
Acquisition Time (sec) 2.3069 Date Oct 4 2018 File Name C:\DOCS\OUTPUT_301\F19\2018.10.04\BM-1378-F_20181004_01\FLUORINE_01Frequency (MHz) 376.32 Nucleus 19F Number of Transients 8 Original Points Count 262144Points Count 262144 Pulse Sequence s2pul Solvent ACETONITRILE-D3Sweep Width (Hz) 113636.37 Temperature (degree C) 22.000
Acquisition Time (sec) 2.5559 Comment Imported from UXNMR. Date 16 Oct 2018 16:12:24File Name C:\DOCS\OUTPUT_301\2018\10.î êòÿáðü\BM-1399-2.H_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 4 Original Points Count 16384 Points Count 65536Pulse Sequence zg30 Solvent ACETONITRILE-D3 Sweep Width (Hz) 6410.26Temperature (degree C) 27.000
Acquisition Time (sec) 1.9000 Comment STANDARD FLUORINE PARAMETERS Date Oct 1 2018File Name C:\DOCS\OUTPUT_301\F19\2018.10.01\BM1375_20181001_01\FLUORINE_01 Frequency (MHz) 376.31Nucleus 19F Number of Transients 16 Original Points Count 169643 Points Count 262144Pulse Sequence s2pul Solvent DMSO-D6 Sweep Width (Hz) 89285.71 Temperature (degree C) 22.000
Acquisition Time (sec) 4.0894 Comment Imported from UXNMR. Date 16 Oct 2018 20:47:00File Name C:\DOCS\OUTPUT_301\2018\10.î êòÿáðü\bm181016\BM-1398-2_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 8 Original Points Count 32768 Points Count 131072Pulse Sequence zg30 Solvent ACETONITRILE-D3 Sweep Width (Hz) 8012.82Temperature (degree C) 27.000
Acquisition Time (sec) 1.9000 Date Oct 1 2018 File Name C:\DOCS\OUTPUT_301\F19\2018.10.01\BM1376_20181001_01\FLUORINE_01Frequency (MHz) 376.31 Nucleus 19F Number of Transients 16 Original Points Count 169643Points Count 262144 Pulse Sequence s2pul Solvent DMSO-D6 Sweep Width (Hz) 89285.71Temperature (degree C) 22.000
Acquisition Time (sec) 4.0894 Comment Imported from UXNMR. Date 18 Mar 2019 15:56:38File Name C:\DOCS\OUTPUT_301\2019\03.ì àðò\BM-1520-2.H_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 4 Original Points Count 32768 Points Count 131072Pulse Sequence zg30 Solvent ACETONITRILE-D3 Sweep Width (Hz) 8012.82Temperature (degree C) 27.000
Acquisition Time (sec) 0.6783 Comment Imported from UXNMR. Date 16 Mar 2019 14:04:18File Name C:\DOCS\OUTPUT_301\2019\03.ì àðò\BM-1520.C_002001r Frequency (MHz) 100.61 Nucleus 13CNumber of Transients 106 Original Points Count 16384 Points Count 131072 Pulse Sequence zgpg30Solvent CHLOROFORM-D Sweep Width (Hz) 24154.59 Temperature (degree C) 27.000
Acquisition Time (sec) 2.3069 Date Mar 14 2019 File Name C:\DOCS\OUTPUT_301\F19\2019.03.14\BM-1511-A-F_20190314_01\FLUORINE_01Frequency (MHz) 376.32 Nucleus 19F Number of Transients 8 Original Points Count 262144Points Count 262144 Pulse Sequence s2pul Solvent ACETONITRILE-D3Sweep Width (Hz) 113636.37 Temperature (degree C) 22.000
Acquisition Time (sec) 4.0894 Comment Imported from UXNMR. Date 18 Mar 2019 16:02:18File Name C:\DOCS\OUTPUT_301\2019\03.ì àðò\BM-1521-2.H_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 4 Original Points Count 32768 Points Count 131072Pulse Sequence zg30 Solvent ACETONITRILE-D3 Sweep Width (Hz) 8012.82Temperature (degree C) 27.000
Acquisition Time (sec) 0.6783 Comment Imported from UXNMR. Date 16 Mar 2019 21:35:50File Name C:\DOCS\BM\190316\BM-1521_002001r Frequency (MHz) 100.61 Nucleus 13C Number of Transients 128Original Points Count 16384 Points Count 131072 Pulse Sequence zgpg30 Solvent CHLOROFORM-DSweep Width (Hz) 24154.59 Temperature (degree C) 27.000
Acquisition Time (sec) 0.7340 Date Mar 19 2019 File Name C:\DOCS\OUTPUT_301\F19\2019.03.19\bm1521-2-f_20190319_01\FLUORINE_01Frequency (MHz) 376.31 Nucleus 19F Number of Transients 1000 Original Points Count 65536Points Count 65536 Pulse Sequence s2pul Solvent ACETONITRILE-D3Sweep Width (Hz) 89285.71 Temperature (degree C) 22.000
Acquisition Time (sec) 4.0894 Comment Imported from UXNMR. Date 12 Mar 2019 14:47:30File Name C:\DOCS\OUTPUT_301\2019\03.ì àðò\BM-1512-P.H_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 4 Original Points Count 32768 Points Count 131072Pulse Sequence zg30 Solvent ACETONITRILE-D3 Sweep Width (Hz) 8012.82Temperature (degree C) 27.000
Acquisition Time (sec) 0.6783 Comment Imported from UXNMR. Date 12 Mar 2019 15:31:56File Name C:\DOCS\OUTPUT_301\2019\03.ì àðò\BM-1512-P.C_002001r Frequency (MHz) 100.61 Nucleus 13CNumber of Transients 1116 Original Points Count 16384 Points Count 131072 Pulse Sequence zgpg30Solvent CHLOROFORM-D Sweep Width (Hz) 24154.59 Temperature (degree C) 27.000
Acquisition Time (sec) 0.7340 Date Mar 12 2019 File Name C:\DOCS\OUTPUT_301\F19\2019.03.12\bm1512-f_20190312_01\FLUORINE_01Frequency (MHz) 376.31 Nucleus 19F Number of Transients 100 Original Points Count 65536Points Count 65536 Pulse Sequence s2pul Solvent ACETONITRILE-D3Sweep Width (Hz) 89285.71 Temperature (degree C) 22.000
Acquisition Time (sec) 4.0894 Comment Imported from UXNMR. Date 18 Oct 2018 22:21:32File Name C:\DOCS\OUTPUT_301\2018\10.î êòÿáðü\bm181018\BM-1404_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 8 Original Points Count 32768 Points Count 131072Pulse Sequence zg30 Solvent Tol Sweep Width (Hz) 8012.82 Temperature (degree C) 27.000
Acquisition Time (sec) 1.0000 Date Oct 19 2018 File Name C:\DOCS\OUTPUT_301\F19\2018.10.19\BM-1404_20181019_01\FLUORINE_01Frequency (MHz) 376.31 Nucleus 19F Number of Transients 32 Original Points Count 89286Points Count 131072 Pulse Sequence s2pul Solvent CHLOROFORM-DSweep Width (Hz) 89285.71 Temperature (degree C) 22.000
Acquisition Time (sec) 2.5559 Comment Imported from UXNMR. Date 03 Oct 2018 17:50:24File Name C:\DOCS\OUTPUT_301\2018\10.î êòÿáðü\BM-1380.H_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 4 Original Points Count 16384 Points Count 65536Pulse Sequence zg30 Solvent CHLOROFORM-D Sweep Width (Hz) 6410.26Temperature (degree C) 27.000
Acquisition Time (sec) 2.3069 Date Oct 4 2018 File Name C:\DOCS\OUTPUT_301\F19\2018.10.04\BM-1380-F_20181004_01\FLUORINE_01Frequency (MHz) 376.32 Nucleus 19F Number of Transients 8 Original Points Count 262144Points Count 262144 Pulse Sequence s2pul Solvent ACETONITRILE-D3Sweep Width (Hz) 113636.37 Temperature (degree C) 22.000
Acquisition Time (sec) 4.0894 Comment Imported from UXNMR. Date 17 Oct 2018 23:22:50File Name C:\DOCS\OUTPUT_301\2018\10.î êòÿáðü\bm181017\BM-1402-2_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 8 Original Points Count 32768 Points Count 131072Pulse Sequence zg30 Solvent ACETONITRILE-D3 Sweep Width (Hz) 8012.82Temperature (degree C) 27.000
Acquisition Time (sec) 0.4999 Comment Imported from UXNMR. Date 17 Oct 2018 17:16:02File Name C:\DOCS\OUTPUT_301\2018\10.î êòÿáðü\BM-1402.C_002001r Frequency (MHz) 100.61Nucleus 13C Number of Transients 128 Original Points Count 12076 Points Count 65536Pulse Sequence zgpg30 Solvent DMSO-D6 Sweep Width (Hz) 24154.59 Temperature (degree C) 27.000
Acquisition Time (sec) 2.3069 Date Oct 18 2018 File Name C:\DOCS\OUTPUT_301\F19\2018.10.18\BM-1402-2-F_20181018_01\FLUORINE_01Frequency (MHz) 376.32 Nucleus 19F Number of Transients 8 Original Points Count 262144Points Count 262144 Pulse Sequence s2pul Solvent ACETONITRILE-D3Sweep Width (Hz) 113636.37 Temperature (degree C) 22.000
Acquisition Time (sec) 2.5559 Comment Imported from UXNMR. Date 04 Oct 2018 08:19:12File Name C:\DOCS\OUTPUT_301\2018\10.î êòÿáðü\BM-1381.H\BM-1381.H_001000fid Frequency (MHz) 400.13Nucleus 1H Number of Transients 4 Original Points Count 16384 Points Count 16384Pulse Sequence zg30 Solvent ACETONITRILE-D3 Sweep Width (Hz) 6410.26Temperature (degree C) 27.000
Acquisition Time (sec) 1.0000 Date Oct 5 2018 File Name C:\DOCS\OUTPUT_301\F19\2018.10.05\BM-1381_20181005_01\FLUORINE_01Frequency (MHz) 376.31 Nucleus 19F Number of Transients 32 Original Points Count 89286Points Count 131072 Pulse Sequence s2pul Solvent ACETONITRILE-D3Sweep Width (Hz) 89285.71 Temperature (degree C) 22.000
Acquisition Time (sec) 4.0894 Comment Imported from UXNMR. Date 27 Oct 2018 22:02:24File Name C:\DOCS\OUTPUT_301\2018\10.î êòÿáðü\bm181027-2\BM-1392-2f_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 8 Original Points Count 32768 Points Count 131072Pulse Sequence zg30 Solvent ACETONITRILE-D3 Sweep Width (Hz) 8012.82Temperature (degree C) 27.000
Acquisition Time (sec) 0.6783 Comment Imported from UXNMR. Date 27 Oct 2018 22:12:02File Name C:\DOCS\OUTPUT_301\2018\10.î êòÿáðü\bm181027-2\BM-1392-2f_002001r Frequency (MHz) 100.61Nucleus 13C Number of Transients 240 Original Points Count 16384 Points Count 131072Pulse Sequence zgpg30 Solvent ACETONITRILE-D3 Sweep Width (Hz) 24154.59Temperature (degree C) 27.000
Acquisition Time (sec) 2.0000 Date Oct 29 2018 File Name C:\DOCS\OUTPUT_301\F19\2018.10.29\BM-1392-2f_20181029_01\FLUORINE_01Frequency (MHz) 376.31 Nucleus 19F Number of Transients 16 Original Points Count 178571Points Count 262144 Pulse Sequence s2pul Solvent ACETONITRILE-D3Sweep Width (Hz) 89285.71 Temperature (degree C) 22.000
Acquisition Time (sec) 2.5559 Comment Imported from UXNMR. Date 17 Oct 2018 17:28:12File Name C:\DOCS\OUTPUT_301\2018\10.î êòÿáðü\BM-1394.H_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 6 Original Points Count 16384 Points Count 65536Pulse Sequence zg30 Solvent ACETONITRILE-D3 Sweep Width (Hz) 6410.26Temperature (degree C) 27.000
Acquisition Time (sec) 2.3069 Date Oct 18 2018 File Name C:\DOCS\OUTPUT_301\F19\2018.10.18\BM-1394-F_20181018_01\FLUORINE_01Frequency (MHz) 376.32 Nucleus 19F Number of Transients 8 Original Points Count 262144Points Count 262144 Pulse Sequence s2pul Solvent ACETONITRILE-D3Sweep Width (Hz) 113636.37 Temperature (degree C) 22.000
Acquisition Time (sec) 4.0894 Comment Imported from UXNMR. Date 06 Jun 2019 19:17:06File Name I:\SPEC_2019_H,C\06.èþ í ü\BM-1604-a_001001r Frequency (MHz) 400.13 Nucleus 1H Number of Transients 8Original Points Count 32768 Points Count 131072 Pulse Sequence zg30 Solvent CHLOROFORM-DSweep Width (Hz) 8012.82 Temperature (degree C) 27.000
1H NMR spectrum of diastereomeric mixture of 3a and 3a’ (400.1 MHz, CDCl3)
S53
26 Aug 2019
Acquisition Time (sec) 1.0000 Date Jun 7 2019 File Name C:\DOCS\OUTPUT_301\F19\2019.06.07\BM-1604-a_20190607_01\FLUORINE_01Frequency (MHz) 376.31 Nucleus 19F Number of Transients 16 Original Points Count 89286Points Count 131072 Pulse Sequence s2pul Solvent CHLOROFORM-DSweep Width (Hz) 89285.71 Temperature (degree C) 21.000
19F NMR spectrum of diastereomeric mixture of 3a and 3a’ (376.5 MHz, CDCl3)S54
26 Aug 2019
Acquisition Time (sec) 4.0894 Comment Imported from UXNMR. Date 31 May 2019 15:12:08File Name C:\DOCS\OUTPUT_301\2019\05.ì àé\BM-1588.H_001001r Frequency (MHz) 400.13 Nucleus 1HNumber of Transients 4 Original Points Count 32768 Points Count 131072 Pulse Sequence zg30Solvent ACETONITRILE-D3 Sweep Width (Hz) 8012.82 Temperature (degree C) 27.000
1H NMR spectrum of 4 (400.1 MHz, CD3CN). Signals of 3a are the result of hydrolysis of 4 during preparation and storing of the NMR sample.
S55
26 Aug 2019
Acquisition Time (sec) 1.0000 Date Jun 3 2019 File Name I:\SPEC_F_2019\2019.06.03\BM-1588_20190603_01\FLUORINE_01Frequency (MHz) 376.31 Nucleus 19F Number of Transients 16 Original Points Count 89286Points Count 131072 Pulse Sequence s2pul Solvent CHLOROFORM-DSweep Width (Hz) 89285.71 Temperature (degree C) 21.000
19F NMR spectrum of 4 (376.5 MHz, CD3CN). Signals of 3a are the result of hydrolysis of 4 during preparation and storing of the NMR sample.
S56
26 Aug 2019
Acquisition Time (sec) 0.6783 Comment Imported from UXNMR. Date 31 May 2019 15:20:20File Name C:\DOCS\OUTPUT_301\2019\05.ì àé\BM-1588.C_002001r Frequency (MHz) 100.61 Nucleus 13CNumber of Transients 161 Original Points Count 16384 Points Count 131072 Pulse Sequence zgpg30Solvent CHLOROFORM-D Sweep Width (Hz) 24154.59 Temperature (degree C) 27.000
13C NMR spectrum of 4 (100.6 MHz, CD3CN). Signals of 3a are the result of hydrolysis of 4 during preparation and storing of the NMR sample.
S57
27 Aug 2019
Acquisition Time (sec) 4.0894 Comment Imported from UXNMR. Date 05 Jun 2019 17:26:50File Name C:\DOCS\OUTPUT_301\2019\06.èþ í ü\BM-1591-a.H_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 4 Original Points Count 32768 Points Count 131072Pulse Sequence zg30 Solvent ACETONITRILE-D3 Sweep Width (Hz) 8012.82Temperature (degree C) 27.000
1H NMR spectrum of mixture of quinoline and methyl 2-((4,4,4-trifluoro-3-oxo-1-phenylbut-1-en-1-yl)thio)acetate 5 (400.1 MHz, CDCl3). The region with signals of compound 5 are highlighted.
S58
27 Aug 2019
Acquisition Time (sec) 4.0894 Comment Imported from UXNMR. Date 05 Jun 2019 17:26:50File Name C:\DOCS\OUTPUT_301\2019\06.èþ í ü\BM-1591-a.H_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 4 Original Points Count 32768 Points Count 131072Pulse Sequence zg30 Solvent ACETONITRILE-D3 Sweep Width (Hz) 8012.82Temperature (degree C) 27.000
1H NMR spectrum of mixture of quinoline and methyl 2-((4,4,4-trifluoro-3-oxo-1-phenylbut-1-en-1-yl)thio)acetate 5 (400.1 MHz, CDCl3). The region with signals of quinoline are highlighted.
S59
27 Aug 2019
Acquisition Time (sec) 1.0000 Date Jun 3 2019 File Name I:\SPEC_F_2019\2019.06.03\BM-1591_20190603_01\FLUORINE_01Frequency (MHz) 376.31 Nucleus 19F Number of Transients 8 Original Points Count 89286Points Count 131072 Pulse Sequence s2pul Solvent CHLOROFORM-DSweep Width (Hz) 89285.71 Temperature (degree C) 21.000
19F NMR spectrum of mixture of quinoline and methyl 2-((4,4,4-trifluoro-3-oxo-1-phenylbut-1-en-1-yl)thio)acetate 5 (376.5 MHz, CDCl3)
S60
27 Aug 2019
Acquisition Time (sec) 0.6783 Comment Imported from UXNMR. Date 05 Jun 2019 17:41:04File Name C:\DOCS\OUTPUT_301\2019\06.èþ í ü\BM-1591-a.C_002001r Frequency (MHz) 100.61 Nucleus 13CNumber of Transients 361 Original Points Count 16384 Points Count 131072 Pulse Sequence zgpg30Solvent CHLOROFORM-D Sweep Width (Hz) 24154.59 Temperature (degree C) 27.000
13C NMR spectrum of mixture of quinoline and methyl 2-((4,4,4-trifluoro-3-oxo-1-phenylbut-1-en-1-yl)thio)acetate 5 (100.6 MHz, CDCl3). The signals of compound 5 are highlighted.
S61
27 Aug 2019
Acquisition Time (sec) 0.6783 Comment Imported from UXNMR. Date 05 Jun 2019 17:41:04File Name C:\DOCS\OUTPUT_301\2019\06.èþ í ü\BM-1591-a.C_002001r Frequency (MHz) 100.61 Nucleus 13CNumber of Transients 361 Original Points Count 16384 Points Count 131072 Pulse Sequence zgpg30Solvent CHLOROFORM-D Sweep Width (Hz) 24154.59 Temperature (degree C) 27.000
13C NMR spectrum of mixture of quinoline and methyl 2-((4,4,4-trifluoro-3-oxo-1-phenylbut-1-en-1-yl)thio)acetate 5 (100.6 MHz, CDCl3). The signals of quinoline are highlighted.
S62
26 Aug 2019
Acquisition Time (sec) 4.0894 Comment Imported from UXNMR. Date 20 Jun 2019 19:27:10File Name C:\Users\BM-1\Downloads\BM-1607\BM-1607_001001r Frequency (MHz) 400.13 Nucleus 1HNumber of Transients 8 Original Points Count 32768 Points Count 131072 Pulse Sequence zg30Solvent CHLOROFORM-D Sweep Width (Hz) 8012.82 Temperature (degree C) 27.000
Acquisition Time (sec) 0.6783 Comment Imported from UXNMR. Date 01 Jun 2019 14:15:34File Name C:\DOCS\OUTPUT_301\2019\06.èþ í ü\BM-1595.C_002001r Frequency (MHz) 100.61 Nucleus 13CNumber of Transients 146 Original Points Count 16384 Points Count 131072 Pulse Sequence zgpg30Solvent ACETONITRILE-D3 Sweep Width (Hz) 24154.59 Temperature (degree C) 27.000
Acquisition Time (sec) 4.0894 Comment Imported from UXNMR. Date 08 Jul 2019 15:50:32File Name C:\DOCS\OUTPUT_301\2019\07.èþ ëü\BM-1623-1.H_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 4 Original Points Count 32768 Points Count 131072Pulse Sequence zg30 Solvent DMSO-D6 Sweep Width (Hz) 8012.82 Temperature (degree C) 27.000
Acquisition Time (sec) 0.7340 Date Jul 5 2019 File Name C:\DOCS\OUTPUT_301\F19\2019.07.05\BM-1623-R_20190705_01\FLUORINE_01Frequency (MHz) 376.31 Nucleus 19F Number of Transients 16 Original Points Count 65536Points Count 65536 Pulse Sequence s2pul Solvent CHLOROFORM-DSweep Width (Hz) 89285.71 Temperature (degree C) 25.000
Acquisition Time (sec) 0.6783 Comment Imported from UXNMR. Date 08 Jul 2019 16:10:16File Name C:\DOCS\OUTPUT_301\2019\07.èþ ëü\BM-1623-1.C_002001r Frequency (MHz) 100.61Nucleus 13C Number of Transients 505 Original Points Count 16384 Points Count 131072Pulse Sequence zgpg30 Solvent DMSO-D6 Sweep Width (Hz) 24154.59 Temperature (degree C) 27.000
Acquisition Time (sec) 4.0894 Comment Imported from UXNMR. Date 28 Sep 2019 10:32:32File Name I:\BM-1716-2\BM-1716-2_001001r Frequency (MHz) 400.13 Nucleus 1H Number of Transients 8Original Points Count 32768 Points Count 131072 Pulse Sequence zg30 Solvent CHLOROFORM-DSweep Width (Hz) 8012.82 Temperature (degree C) 27.000
Acquisition Time (sec) 2.0000 Date Sep 30 2019 File Name C:\DOCS\OUTPUT_301\F19\2019.09.30\BM-1716-2_20190930_01\FLUORINE_01Frequency (MHz) 376.31 Nucleus 19F Number of Transients 16 Original Points Count 178571Points Count 262144 Pulse Sequence s2pul Solvent CHLOROFORM-DSweep Width (Hz) 89285.71 Temperature (degree C) 20.000
Acquisition Time (sec) 0.6783 Comment Imported from UXNMR. Date 28 Sep 2019 11:10:38File Name I:\BM-1716-2\BM-1716-2_002001r Frequency (MHz) 100.61 Nucleus 13C Number of Transients 904Original Points Count 16384 Points Count 131072 Pulse Sequence zgpg30 Solvent CHLOROFORM-DSweep Width (Hz) 24154.59 Temperature (degree C) 27.000
Acquisition Time (sec) 1.3664 Comment Imported from UXNMR. Date 30 Sep 2019 16:01:36File Name I:\SPEC_2019_H,C\09.ñåí òÿáðü\BM-1716-2.APT_004001r Frequency (MHz) 100.61 Nucleus 13CNumber of Transients 49 Original Points Count 32768 Points Count 131072 Pulse Sequence jmodSolvent ACETONITRILE-D3 Sweep Width (Hz) 23980.81 Temperature (degree C) 27.000
13C APT NMR spectrum of 8 and 9 (100.6 MHz, CDCl3)
S74
3 Oct 2019
Acquisition Time (sec) 1.0000 Date Sep 20 2019 File Name C:\DOCS\OUTPUT_301\F19\2019.09.20\BM-1709-R_20190920_01\FLUORINE_01Frequency (MHz) 376.31 Nucleus 19F Number of Transients 8 Original Points Count 89286Points Count 131072 Pulse Sequence s2pul Solvent CHLOROFORM-DSweep Width (Hz) 89285.71 Temperature (degree C) 20.000
19F NMR monitoring of hydrogenation of 3a in MeOH.Spectrum of the reaction mixture after first 14 h (376.5 MHz CDCl3)
S75
3 Oct 2019
Acquisition Time (sec) 4.0894 Comment Imported from UXNMR. Date 28 Sep 2019 16:54:48File Name C:\DOCS\BM\BM-1709-f\BM-1709-f_001001r Frequency (MHz) 400.13 Nucleus 1H Number of Transients 8Original Points Count 32768 Points Count 131072 Pulse Sequence zg30 Solvent CHLOROFORM-DSweep Width (Hz) 8012.82 Temperature (degree C) 27.000
Acquisition Time (sec) 2.0000 Date Sep 30 2019 File Name C:\DOCS\OUTPUT_301\F19\2019.09.30\BM-1709-F_20190930_01\FLUORINE_01Frequency (MHz) 376.31 Nucleus 19F Number of Transients 16 Original Points Count 178571Points Count 262144 Pulse Sequence s2pul Solvent CHLOROFORM-DSweep Width (Hz) 89285.71 Temperature (degree C) 20.000
Acquisition Time (sec) 0.6783 Comment Imported from UXNMR. Date 30 Sep 2019 15:45:06File Name I:\SPEC_2019_H,C\09.ñåí òÿáðü\BM-1709-F.C_002001r Frequency (MHz) 100.61 Nucleus 13CNumber of Transients 161 Original Points Count 16384 Points Count 131072 Pulse Sequence zgpg30Solvent CHLOROFORM-D Sweep Width (Hz) 24154.59 Temperature (degree C) 27.000
Acquisition Time (sec) 1.3664 Comment Imported from UXNMR. Date 30 Sep 2019 15:49:36File Name C:\DOCS\OUTPUT_301\2019\09.ñåí òÿáðü\BM-1709-F.APT_004001r Frequency (MHz) 100.61Nucleus 13C Number of Transients 33 Original Points Count 32768 Points Count 131072Pulse Sequence jmod Solvent ACETONITRILE-D3 Sweep Width (Hz) 23980.81Temperature (degree C) 27.000
Acquisition Time (sec) 4.0894 Comment Imported from UXNMR. Date 27 Sep 2019 15:28:36File Name C:\DOCS\OUTPUT_301\2019\09.ñåí òÿáðü\BM-1709-K.H_001001r Frequency (MHz) 400.13Nucleus 1H Number of Transients 4 Original Points Count 32768 Points Count 131072Pulse Sequence zg30 Solvent CHLOROFORM-D Sweep Width (Hz) 8012.82Temperature (degree C) 27.000
Acquisition Time (sec) 1.0000 Date Sep 27 2019 File Name C:\DOCS\OUTPUT_301\F19\2019.09.27\BM-1709-K_20190927_01\FLUORINE_01Frequency (MHz) 376.31 Nucleus 19F Number of Transients 4 Original Points Count 89286Points Count 131072 Pulse Sequence s2pul Solvent CHLOROFORM-DSweep Width (Hz) 89285.71 Temperature (degree C) 20.000
Acquisition Time (sec) 0.6783 Comment Imported from UXNMR. Date 27 Sep 2019 15:38:00File Name C:\DOCS\OUTPUT_301\2019\09.ñåí òÿáðü\BM-1709-K.C_002001r Frequency (MHz) 100.61Nucleus 13C Number of Transients 233 Original Points Count 16384 Points Count 131072Pulse Sequence zgpg30 Solvent CHLOROFORM-D Sweep Width (Hz) 24154.59Temperature (degree C) 27.000
Acquisition Time (sec) 1.3664 Comment Imported from UXNMR. Date 30 Sep 2019 15:55:04File Name C:\DOCS\OUTPUT_301\2019\09.ñåí òÿáðü\BM-1709-R.APT_004001r Frequency (MHz) 100.61Nucleus 13C Number of Transients 34 Original Points Count 32768 Points Count 131072Pulse Sequence jmod Solvent ACETONITRILE-D3 Sweep Width (Hz) 23980.81Temperature (degree C) 27.000