CN103087100A - Synthesis method of alpha-aminophosphonate - Google Patents

Synthesis method of alpha-aminophosphonate Download PDF

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CN103087100A
CN103087100A CN2013100666906A CN201310066690A CN103087100A CN 103087100 A CN103087100 A CN 103087100A CN 2013100666906 A CN2013100666906 A CN 2013100666906A CN 201310066690 A CN201310066690 A CN 201310066690A CN 103087100 A CN103087100 A CN 103087100A
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nmr
cdcl
aminophosphonate
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aminophosphonicacid
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何林
杜广芬
蔡志华
范业成
代斌
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何林
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

The invention relates to a method for preparing alpha-aminophosphonate from raw materials trimethylsiloxy dimethyl phosphite and imine by autocatalytic phosphine hydrogenation reaction without any catalyst. The invention aims to solve the problems of overhigh catalyst consumption, metal pollution, poor substrate compatibility and the like in the synthesis of alpha-aminophosphonate and derivatives thereof, and provides a new method for synthesizing alpha-aminophosphonate without any catalyst. The invention can be used for preparing alpha-aminophosphonate compounds with different protective groups on the nitrogen atom.

Description

A kind of α-aminophosphonicacid ester synthesis method
Technical field
The present invention relates to field of fine chemical, relate in particular to a kind of organic synthesis intermediate α-aminophosphonicacid ester.Particularly, relate under the catalyst-free effect, by autocatalysis phosphine hydrogenation, prepare the method for α-aminophosphonicacid ester take trimethylsiloxy group dimethylphosphite and imines as raw material.
Background technology
α-aminophosphonicacid ester and derivative thereof have the important intermediate compound of biological activity and pharmaceutical activity, have been widely used at present doing the aspects such as microbiotic, sterilant, enzyme inhibitors, weedicide, have therefore caused the great interest of organic chemist.Pudovik reaction (hydrogen phosphorus acylation reaction) is the method for synthesizing the most direct, the simplest of α-aminophosphonicacid and derivative thereof and being widely used.In recent years, the chemist has been developed much and has been reacted the method for constructing carbon phosphine key by Pudovic, as under transition metal or organic micromolecule catalyst effect, phosphorous acid ester and aldehyde, ketone, imines etc. prepare corresponding phosphine hydrogenated products by the addition reaction of electrophilic reagent.Yet the trimethylsiloxy group dimethylphosphite is as a kind of good nucleophilic reagent, and the report that reacts (hydrogen phosphorus acylation reaction) synthetic α-aminophosphonicacid ester and derivative thereof by Pudovik with imines but seldom.Recently, the reports such as B.Das use the trimethylsiloxy group dimethylphosphite as nucleophilic reagent, at I 2Under Journal of Molecular Catalysis, to Methyl benzenesulfonyl base imine reaction, obtain the α-aminophosphonicacid ester with higher productive rate.We also find recently, and N-heterocyclic carbine (NHCs) the effectively Pudovik of the trimethyl silicon based dimethylphosphite of catalysis and aldehyde reacts, and obtains alpha-hydroxyphosphonate with higher productive rate.NHCs catalysis is as the part of research, and we attempt the Pudovik reaction of the trimethyl silicon based dimethylphosphite of N-heterocyclic carbine (NHCs) catalysis and aldimine.In this article, we have developed a kind of method of trimethyl silicon based dimethylphosphite and aldimine direct-coupling generation α-aminophosphonicacid.
The present invention on this basis, study trimethylsiloxy group dimethylphosphite and imines and reacted the reaction of preparation α-aminophosphonicacid ester by Pudovic, discovery is under the condition that exists without any catalyzer, trimethylsiloxy group dimethylphosphite and imines can autocatalysis generation additions, obtain the α-aminophosphonicacid ester cpds with outstanding productive rate.
Summary of the invention
Purpose of the present invention:
One, provide under a kind of catalyst-free effect, trimethylsiloxy group dimethylphosphite and imines prepare the α-aminophosphonicacid ester cpds by the autocatalysis addition reaction.
Two, by changing the protecting group of substrate imines and nitrogen-atoms, can synthesize the α-aminophosphonicacid ester cpds of multiple different structure.
Of the present invention is a kind of by self-catalyzed reaction, the novel method of preparation α-aminophosphonicacid ester cpds.Particularly, trimethylsiloxy group dimethylphosphite and imines are raw material, by intermolecular phosphine hydrogenation, and efficiently synthetic α-aminophosphonicacid ester cpds.By changing the protecting group of substrate imines and nitrogen-atoms, can synthesize the α-aminophosphonicacid ester cpds of multiple different structure, react as follows:
Figure BSA00000860241000021
In reaction (I), the R group can be aromatic base or hetero-aromatic ring or alkyl base, and nitrogen atom protecting group PG can be benzenesulfonyl or the tertbutyloxycarbonyl of various replacements.
The method for preparing the α-aminophosphonicacid ester provided by the present invention have the reaction conditions gentleness, simple to operate, need not the advantages such as catalyzer.
Embodiment
Following example has further been explained synthetic method of the present invention, but does not limit the scope of the invention.
Instrument and medicine
The practical Agilent7890A/5975C GC-MS of gas chromatograph-mass spectrometer; Proton nmr spectra (400MHz) adopts the U.S. INOVA-400MHz of Varian company type nmr determination, uses CDCl 3Be solvent, TMS is interior mark; Infrared spectrogram is measured with Nicolet AVATAR-360FT-IR infrared spectrometer (KBr compressing tablet).Chemical reagent is available from Sigma-Adrich, Alfa-Aser company, and the lark waffle is learned, Aladdin chemical reagents corporation.
Example: (tolysulfonyl amido) phenmethyl dimethyl phosphate 1a
Add 3.6mmol phenyl Tos imines 1a in the Shrek bottle of 50mL drying, and add anhydrous THF (24mL) stirring and dissolving, then be cooled to 0 ℃.The new trimethylsiloxyphosphite (5.4mmol, 1.03mL) that steams adds in reaction flask under the N2 protection by microsyringe.Remove ice bath, reaction mixture at room temperature reacts to add distilled water (5mL) in the backward reaction flask of 24h and continue and stirred 30 minutes, and (3 * 60mL) extractions merge organic phase to reaction mixture, add anhydrous Na 2SO4 dry by CH2Cl2.After vacuum was spin-dried for solvent, crude product separates by column chromatography can obtain pure target product (silica gel, PE-EtOAc, 1: 1).
(tolysulfonyl amido) phenmethyl dimethyl phosphate 1a
White solid, productive rate 91%, fusing point 163-164 ℃; 1H NMR (300MHz, CDCl 3) δ 7.53-7.38 (m, 3H), 7.32-7.18 (m, 2H), (7.17-7.02 m, 3H), 7.00-6.88 (d, J=7.9Hz, 2H), 4.85 (dd, J=24.2,9.9Hz, 1H), 3.89 (d, J=10.7Hz, 3H), 3.39 (d, J=10.5Hz, 3H), 2.24 (s, 3H); 13C NMR (75MHz, CDCl 3) δ 142.7,137.9,133.3,128.9,128.3,128.2,127.8 (d, J=3.0Hz), 127.0,54.9 (d, J=156.7Hz), 54.6 (d, J=6.7Hz), 53.9 (d, J=6.7Hz), 21.3.
(tolysulfonyl amido) (4-aminomethyl phenyl) methyl-phosphoric acid dimethyl ester 1b
White solid, productive rate 95%, fusing point 187-189 ℃; 1H NMR (400MHz, CDCl 3) δ 7.47 (d, J=8.2Hz, 2H), 7.19-6.86 (m, 6H), 6.82 (br s, NH), 4.78 (dd, J=23.9,9.8Hz, 1H), 3.84 (d, J=10.8Hz, 3H), 3.41 (d, J=10.6Hz, 3H), 2.29 (s, 3H), 2.25 (s, 3H); 13C NMR (100MHz, CDCl 3) δ 142.7,137.8 (d, J=4.0Hz), 130.2,128.97,128.94, (128.0 d, J=6.0Hz), 127.0,54.6 (d, J=156.0Hz), 54.4 (d, J=7.0Hz), 53.9 (d, J=7.0Hz), 21.3,21.0.
(tolysulfonyl amido) (4-p-methoxy-phenyl) methyl-phosphoric acid dimethyl ester 1c
White solid, productive rate 86%, fusing point 160-161 ℃; 1H NMR (400MHz, CDCl 3) δ 7.47 (d, J=8.3Hz, 2H), 7.12 (dd, J=8.6,1.8Hz, 2H), 7.00 (d, J=8.0Hz, 2H), (6.72 br s, NH), 6.63 (d, J=8.5Hz, 2H), (4.77 dd, J=24.6,10.1Hz, 1H), 3.85 (d, J=10.8Hz, 3H), 3.73 (s, 3H), 3.42 (d, J=10.6Hz, 3H), 2.29 (s, 3H); 13C NMR (100MHz, CDCl 3) δ 159.3 (d, J=3.0Hz), 142.8,137.8 (d, J=2.0Hz), 129.3 (d, J=6.0Hz), 129.0,127.0,125.3,113.7 (d, J=2.0Hz), 55.2,54.4 (d, J=7.0Hz), 54.2 (d, J=157.0Hz), (53.9 d, J=7.0Hz), 21.3.
(tolysulfonyl amido) (4-fluorophenyl) methyl-phosphoric acid dimethyl ester 1d
White solid, productive rate 83%, fusing point 209-210 ℃; 1H NMR (400MHz, CDCl 3) δ 7.48 (s, 1H), 7.46 (s, 1H), (7.23-7.16 m, 3H), 7.00 (d, J=8.0Hz, 2H), 6.78 (t, J=8.5Hz, 2H), (4.83 dd, J=24.2,9.8Hz, 1H), (3.90 d, J=10.8Hz, 3H), 3.46 (d, J=10.7Hz, 3H), 2.29 (s, 3H); 13C NMR (100MHz, CDCl 3) δ 162.4 (dd, J=246.0,3.0Hz), 143.1, (137.8 d, J=1.0Hz), 129.9 (dd, J=8.0,5.0Hz), 129.2 (d, J=4.0Hz), 129.0,127.0,115.2 (dd, J=22.0,2.0Hz), (54.8 d, J=8.0Hz), 54.2 (dd, J=157.0Hz), (53.9 d, J=7.0Hz), 21.4.
(tolysulfonyl amido) (4-chloro-phenyl-) methyl-phosphoric acid dimethyl ester 1e
White solid, productive rate 82%, fusing point 198-199 ℃; 1H NMR (400MHz, CDCl 3) δ 7.45 (d, J=8.3Hz, 2H), 7.20 (br s, NH), (7.17-7.10 m, 2H), 7.04 (d, J=8.3Hz, 2H), 6.99 (d, J=8.0Hz, 2H), (4.82 dd, J=24.4,9.9Hz, 1H), (3.91 d, J=10.8Hz, 3H), 3.47 (d, J=10.7Hz, 3H), 2.31 (s, 3H); 13C NMR (100MHz, CDCl 3) δ 143.2,137.6 (d, J=2.0Hz), 134.0 (d, J=4.0Hz), 131.9,129.5 (d, J=5.0Hz), 129.0,128.4 (d, J=2.0Hz), 127.0,54.3 (d, J=157.0Hz), 54.8 (d, J=7.0Hz), (53.9 d, J=7.0Hz), 21.3.
(tolysulfonyl amido) (4-trifluoromethyl) methyl-phosphoric acid dimethyl ester 1f
White solid, productive rate 99%, fusing point 228-230 ℃; 1H NMR (400MHz, CDCl 3) δ 8.91 (dd, J=10.6,2.4Hz, 1H), 7.41 (s, 4H), 7.40 (s, 1H), 7.01 (d, J=8.0Hz, 2H), 4.98 (dd, J=24.9,10.6Hz, 1H), 3.70 (d, J=10.7Hz, 3H), (3.49 d, J=10.7Hz, 3H), 3.35 (br s, NH, 1H), 2.19 (s, 3H); 13C NMR (100MHz, CDCl 3) δ 142.3,138.6,137.7 (d, J=1.0Hz), (128.9 d, J=5.0Hz), 128.8,127.7 (dd, J=31.0,3.0Hz), 126.5,124.4, (124.0 d, J=271.0Hz), 53.9 (d, J=7.0Hz), 53.3 (d, J=155.0Hz), (53.2 d, J=7.0Hz), 20.5.
(tolysulfonyl amido) (4-nitrophenyl) methyl-phosphoric acid dimethyl ester 1g
White solid, productive rate 98%, fusing point 207-208 ℃; 1H NMR (400MHz, DMSO-d 6) δ 8.98 (d, J=8.3Hz, 1H), 7.94 (d, J=8.7Hz, 2H), 7.50 (dd, J=8.8,2.0Hz, 2H), (7.44 d, J=8.3Hz, 2H), 7.07 (d, J=8.3Hz, 2H), 5.09 (dd, J=25.4,10.3Hz, 1H), (3.69 d, J=10.7Hz, 3H), 3.49 (d, J=10.8Hz, 3H), 2.19 (s, 3H); 13C NMR (100MHz, DMSO-d 6) δ 146.7 (d, J=3.0Hz), 142.8,142.2,138.0,129.7 (d, J=5.0Hz), 129.2,126.8,122.9,54.2 (d, J=7.0Hz), 53.6 (d, J=7.0Hz), 53.4 (d, J=142.0Hz), 20.9.
(tolysulfonyl amido) (2-p-methoxy-phenyl) methyl-phosphoric acid dimethyl ester 1h
White solid, productive rate 86%, fusing point 189-190 ℃; 1H NMR (400MHz, CDCl 3) δ 7.48 (s, 1H), 7.46 (s, 1H), (7.25 dt, J=9.6,1.9Hz, 1H), (7.02-7.06 m, 1H), 6.95 (d, J=8.0Hz, 2H), 6.70 (t, J=7.5Hz, 1H), (6.64 br d, J=7.8Hz, 1H), 6.61 (d, J=8.3Hz, 1H), 5.30 (dd, J=24.6,10.5Hz, 1H), 3.87 (d, J=10.7Hz, 3H), 3.74 (s, 3H), 3.44 (d, J=10.6Hz, 3H), 2.25 (s, 3H); 13C NMR (100MHz, CDCl 3) δ 156.4 (d, J=6.0Hz), 142.8,137.3 (d, J=2.0Hz), 129.5 (d, J=5.0Hz), 129.2 (d, J=3.0Hz), 128.8,127.0,121.8, (127.0 d, J=2.0Hz), 110.5 (d, J=2.0Hz), 55.6,54.4 (d, J=7.0Hz), 53.8 (d, J=7.0Hz), 49.0 (d, J=161.0Hz), 21.3.
(tolysulfonyl amido) (3-p-methoxy-phenyl) methyl-phosphoric acid dimethyl ester 1i
White solid, productive rate 78%, fusing point 163-164 ℃; 1H NMR (400MHz, CDCl 3) δ 7.48 (s, 1H), 7.46 (s, 1H), 7.39 (br d, J=6.4Hz, 1H), 7.00 (t, J=7.7Hz, 1H), 6.95 (d, J=8.0Hz, 2H), 6.78 (d, J=7.5Hz, 1H), 6.73 (s, 1H), (6.64 d, J=8.2Hz, 1H), 4.85 (dd, J=24.5,10.2Hz, 1H), 3.93 (d, J=10.8Hz, 3H), 3.52 (s, 3H), (3.43 d, J=10.6Hz, 3H), 2.26 (s, 3H); 13C NMR (100MHz, CDCl 3) δ 159.5 (d, J=2.0Hz), 142.8,137.9,134.5,129.2 (d, J=2.0Hz), 128.8,127.1,120.7 (d, J=6.0Hz), 114.2, (113.0 d, J=5.0Hz), 55.1 (d, J=157.0Hz), 54.9,54.8 (d, J=7.0Hz), (53.9 d, J=7.0Hz), 21.3.
(tolysulfonyl amido) (2-chloro-phenyl-) methyl-phosphoric acid dimethyl ester 1j
White solid, productive rate 91%, fusing point 223-224 ℃; IR3152,2954,1449,1334,1239,1156,1065,1033cm -1 1H NMR (400MHz, CDCl 3) δ 7.52 (d, J=8.2Hz, 2H), 7.47 (d, J=7.8Hz, 1H), 7.18 (d, J=7.9Hz, 2H), 7.05 (t, J=7.4Hz, 3H), 6.96 (d, J=8.0Hz, 2H), (5.50 dd, J=24.6,10.1Hz, 1H), (3.95 d, J=10.8Hz, 3H), 3.44 (d, J=10.7Hz, 3H), 2.25 (s, 3H); 13C NMR (100MHz, CDCl 3) δ 142.9,137.2,133.3 (d, J=7.0Hz), 131.6,129.6 (d, J=4.0Hz), 129.1 (d, J=2.0Hz), 129.0,126.9, (126.8 d, J=3.0Hz), 54.8 (d, J=7.0Hz), 54.0 (d, J=7.0Hz), (50.5 d, J=158.0Hz), 21.3; HRMS (ESI) calcdfor C 16H 19ClNO 5PSNa (MNa +) 426.0308, found426.0313.
(tolysulfonyl amido) furfuryl dimethyl phosphate 1k
White solid, productive rate 99%, fusing point 163-164 ℃; 1H NMR (400MHz, CDCl 3) δ 7.57 (d, J=8.4Hz, 2H), 7.19-7.07 (m, 3H), 6.32-6.01 (m, 3H), (4.92 dd, J=24.1,10.1Hz, 1H), 3.85 (d, J=10.8Hz, 3H), 3.58 (d, J=10.8Hz, 3H), 2.35 (s, 3H); 13C NMR (100MHz, CDCl 3) δ 146.5,143.1,142.6 (d, J=3.0Hz), 137.3,129.2,126.9,110.6 (d, J=2.0Hz), 109.7 (d, J=7.0Hz), 54.6 (d, J=7.0Hz), 53.9 (d, J=7.0Hz), 48.5 (d, J=163.0Hz), 21.4.
(tolysulfonyl amido)-2-naphthyl methyl dimethyl phosphate 1l
White solid, productive rate 92%, fusing point 172-173 ℃; IR3437,3108,2950,1457,1326,1235,1164,1057,1029cm -1 1H NMR (400MHz, CDCl 3) δ 7.71 (d, J=8.0Hz, 1H), 7.60 (s, 1H), (7.54 d, J=8.5Hz, 2H), 7.50 (d, J=8.0Hz, 2H), 7.46-7.34 (m, 5H), 7.29 (br s, NH), (6.69 d, J=8.0Hz, 2H), 5.02 (dd, J=24.2,10.0Hz, 1H), 3.96 (d, J=10.8Hz, 3H), (3.43 d, J=10.6Hz, 3H), 1.94 (s, 3H); 13C NMR (100MHz, CDCl 3) δ 142.8,137.7 (d, J=2.0Hz), 132.8 (d, J=2.0Hz), (132.7 dd, J=6.0,2.0Hz), 130.3,128.7, (128.1 d, J=1.0Hz), 127.9,127.8 (d, J=8Hz), 127.3,126.9,126.2,126.0,125.6 (d, J=4.0Hz), 55.3 (d, J=157.0Hz), 54.8 (d, J=7.0Hz), 54.0 (d, J=7.0Hz), 20.9; HRMS (ESI) calcd for C 20H 22NO 5PSNa (MNa +) 442.0854, found442.0871.
(tolysulfonyl amido) butyl phosphoric acid dimethyl ester 1m
White solid, productive rate 63%, fusing point 117-118 ℃; 1H NMR (400MHz, CDCl 3) δ 7.76 (d, J=8.2Hz, 2H), 7.29 (d, J=8.2Hz, 2H), 5.40 (br s, NH), 3.66 (d, J=1.3Hz, 3H), 3.63 (d, J=1.1Hz, 3H), (2.42 s, 3H), 1.77-1.60 (m, 1H), (1.58-1.32 m, 2H), 1.31-1.18 (m, 2H), (0.79 dt, J=7.3,1.9Hz, 3H); 13CNMR (100MHz, CDCl 3) δ 143.3,138.3,129.4,127.0,53.5 (d, J=7.0Hz), 52.9 (d, J=7.0Hz), 49.7 (d, J=157.0Hz), 32.5 (d, J=3.0Hz), 21.5,18.7 (d, J=10.0Hz), 13.6.
(tolysulfonyl amido) cyclohexyl methyl dimethyl phosphate 1n
White solid, productive rate 95%, fusing point 160-161 ℃; IR3152,2950,2922,2847,1465,1322,1235,1152,1105,1057,1013cm -1 1H NMR (400MHz, CDCl 3) δ 7.75 (d, J=8.0Hz, 2H), 7.39-7.18 (m, 2H), 3.59 (d, J=10.7Hz, 3H), 3.53 (d, J=10.7Hz, 3H), 2.42 (s, 3H), 1.80-1.55 (m, 6H), 1.22-1.00 (m, 5H); 13CNMR (100MHz, CDCl 3) δ 143.2,138.4,129.3,127.1, (54.8 d, J=151.0Hz), 52.8 (d, J=7.0Hz), (52.7 d, J=6.0Hz), 39.2 (d, J=4.0Hz), (30.4 d, J=11.0Hz), 28.0 (d, J=3.0Hz), 26.1 (d, J=1.0Hz), 26.0,25.7,21.5; HRMS (ESI) calcd for C 16H 26NO 5PSNa (MNa +) 398.1167, found398.1142.
(tertbutyloxycarbonyl amido) phenmethyl dimethyl phosphate 1o
White solid, productive rate 94%, fusing point 110-113 ℃; 1H NMR (400MHz, CDCl 3) δ 7.44-7.30 (m, 5H), 5.54 (brs, NH, 1H), 5.15 (dd, J=21.4,9.9Hz, 1H), 3.77 (d, J=10.7Hz, 3H), 3.50 (d, J=10.6Hz, 3H), 1.43 (s, 9H); 13C NMR (100MHz, CDCl 3) δ 154.8 (d, J=9.0Hz), 135.1,128.7,128.1 (d, J=3.0Hz), (127.7 d, J=5.0Hz), 80.5,53.7 (d, J=7.0Hz), (53.6 d, J=7.0Hz), 51.4 (d, J=153.0Hz), 28.2.
(p-nitrophenyl sulfoamido) phenmethyl dimethyl phosphate 1p
Yellow solid, productive rate 95%, fusing point 240-241 ℃; 1H NMR (400MHz, CDCl 3) δ 8.28 (d, J=6.4Hz, 1H), 7.96-7.90 (m, 2H), 7.76-7.69 (m, 2H), 7.23 (br s, NH), 7.21 (d, J=1.7Hz, 1H), (7.16-7.02 m, 3H), 4.94 (dd, J=24.4,10.2Hz, 1H), 4.02 (d, J=10.9Hz, 3H), 3.42 (d, J=10.7Hz, 3H); 13C NMR (100MHz, CDCl 3) δ 149.3,146.8 (d, J=2.0Hz), 132.5,128.5 (d, J=3.0Hz), (128.4 d, J=2.0Hz), 128.3 (d, J=6.0Hz), 128.2,123.3, (55.2 d, J=158.0Hz), 54.8 (d, J=7.0Hz), 54.3 (d, J=8.0Hz).

Claims (3)

1. trimethylsiloxy group dimethylphosphite and the imines of following formula (I) expression, under the catalyst-free effect, by autocatalysis phosphine hydrogenation, prepare the phosphine hydrogenation of α-aminophosphonicacid ester, synthetic α-aminophosphonicacid ester.
Figure FSA00000860240900011
2. the preparation of α-aminophosphonicacid ester according to claim 1 is characterized in that not adding any catalyzer.
3. the preparation of α-aminophosphonicacid ester according to claim 1, R group can be aromatic base or hetero-aromatic ring or alkyl base, and nitrogen atom protecting group PG can be benzenesulfonyl or the tertbutyloxycarbonyl of various replacements.
CN2013100666906A 2013-03-04 2013-03-04 Synthesis method of alpha-aminophosphonate Pending CN103087100A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115974919A (en) * 2022-11-14 2023-04-18 石河子大学 2- (triphenyl phosphonium) benzene sulfonate derivative and preparation method thereof
CN116178229A (en) * 2022-11-14 2023-05-30 石河子大学 N-acyl sulfilimine compound and preparation method thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115974919A (en) * 2022-11-14 2023-04-18 石河子大学 2- (triphenyl phosphonium) benzene sulfonate derivative and preparation method thereof
CN116178229A (en) * 2022-11-14 2023-05-30 石河子大学 N-acyl sulfilimine compound and preparation method thereof
CN116178229B (en) * 2022-11-14 2024-03-15 石河子大学 N-acyl sulfilimine compound and preparation method thereof
CN115974919B (en) * 2022-11-14 2024-04-16 石河子大学 2- (Triphenylphosphine) benzenesulfonate derivative and preparation method thereof

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