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(e)-Synthetic method of alkenyl sulfone compounds

A synthesis method and compound technology, applied in the field of organic chemical synthesis, can solve problems such as being unsuitable for large-scale production

Active Publication Date: 2020-05-26
SHIJIAZHUANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods all use dangerous peroxides as raw materials and are not suitable for large-scale production.

Method used

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  • (e)-Synthetic method of alkenyl sulfone compounds
  • (e)-Synthetic method of alkenyl sulfone compounds

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] In the reactor, add 148mg (1mmol) cinnamic acid, 206mg (1.2mmol) benzenesulfonyl hydrazide, 66.4mg (0.4mmol) KI, 22.6mg (0.1mmol) SbCl 3 , 35.4 mg (0.6 mmol) CuSO 4 , 300mg (2.5mmol) of styrene oxide and 7mL of MeCN, stirred, then added 689mg (6mmol) of 30% H 2 o 2 , react at room temperature for 1h, add 15mL saturated NaHSO 3 solution, stirred for 20min, distilled off MeCN under reduced pressure, then added 10mL of ethyl acetate and 10mL of H 2 O, separate layers, extract with ethyl acetate, dry, filter, concentrate the filtrate, purify by silica gel column chromatography (petroleum ether / ethyl acetate 20:1), get ( E )-(benzenesulfonyl)vinylbenzene, yield 63.2%. mp 69-71°C; 1 H NMR (400MHz, CDCl 3 ) δ 7.95(d, J =15.2Hz, 1H),7.69(d, J =15.2Hz, 1H), 7.62(t, J =7.2Hz, 1H), 7.55(t, J =7.6Hz, 2H), 7.50-7.47(m, 2H), 7.42-7.37 (m, 3H), 6.87(d, J =15.2Hz, 1H).

Embodiment 2

[0015] In the reactor, add 178 mg (1 mmol) 4-methoxycinnamic acid, 242 mg (1.2 mmol) 4-methoxybenzenesulfonyl hydrazide, 66.4 mg (0.4 mmol) KI, 22.6 mg (0.1 mmol) SbCl 3 , 73.2 mg (0.55 mmol) CuCl 2 , 216mg (3mmol) of 1,2-epoxybutane and 7mL of MeCN, stirred, then added 804mg (7mmol) of 30% H 2 o 2 , react at room temperature for 1h, add 15mL saturated NaHSO 3 solution, stirred for 20min, distilled off MeCN under reduced pressure, then added 10mL of ethyl acetate and 10mL of H 2 O, separate layers, extract with ethyl acetate, dry, filter, concentrate the filtrate, purify by silica gel column chromatography (petroleum ether / ethyl acetate 20:1), get ( E )-1-methoxy-4-(2-((4-methoxyphenyl)sulfonyl)alkenyl)benzene, yield 74.7%. 1 H NMR (400MHz, CDCl 3 ) δ 7.88(d, J =8.7Hz, 2H), 7.60(d, J =15.3Hz, 1H), 7.42(t, J =8.7Hz, 2H), 7.01(d, J =9.0Hz,2H), 6.90(d, J =8.7Hz, 2H), 6.72(d, J =15.6Hz,1H), 3.86(s, 3H), 3.83(s, 3H).

Embodiment 3

[0017] In the reactor, add 162 mg (1 mmol) 4-methylcinnamic acid, 233 mg (1.2 mmol) n-octylsulfonyl hydrazide, 66.4 mg (0.4 mmol) KI, 22.6 mg (0.1 mmol) SbCl 3 , 108.6 mg (0.6 mmol) Cu(OAc) 2 , 174mg (3mmol) 1,2-propylene oxide and 7mLMeCN, stirred, then added 804mg (7mmol) 30% H 2 o 2 , react at room temperature for 1h, add 15mL saturated NaHSO 3 solution, stirred for 20min, distilled off MeCN under reduced pressure, then added 10mL of ethyl acetate and 10mL of H 2 O, separate layers, extract with ethyl acetate, dry, filter, concentrate the filtrate, purify by silica gel column chromatography (petroleum ether / ethyl acetate 20:1), get ( E )-1-methyl-4-(2-(octylsulfonyl)alkenyl)benzene, yield 73.9%. 1 H NMR (400MHz, CDCl 3 ) δ 7.60(d, J =15.0Hz,1H), 7.43(d, J =7.8Hz, 2H), 7.24(d, J =7.8Hz, 2H), 6.79(d, J =15.6Hz, 1H), 3.06-2.91(m, 2H), 2.39(s, 3H), 1.84-1.75(m, 2H), 1.27-1.22(m, 8H), 8.07(t, J =6.9Hz, 3H).

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Abstract

The invention discloses a synthesis method of a (E)-vinyl sulfone compound. The synthesis method comprises the following steps: using acetonitrile as a solvent, under the catalysis of SbCl3, oxidizingand reducing 1,2-alkylene oxide compound (IV) to generate beta-peroxy alcohols compound (V) as well as oxidizing and reducing KI to generate I2 by 30% H2O2 at the same time.In the presence of Cu (II)salt, I2 and the compound (V) catalyze the reaction of cinnamate compound (II) and sulfonyl hydrazide compound (III), and (E)-vinyl sulfone compound (I) is synthesized by decarboxylation and denitrification.The invention has the advantages that raw materials can be easily obtained, peroxide reagent beta-peroxy alcohols compound and iodine are generated in situ, the method provided by the invention is safe and economic, and iodine-containinged compound can be recycled.

Description

technical field [0001] The present invention relates to the field of organic chemical synthesis, specifically ( E )-The synthetic method of alkenyl sulfone compound. Background technique [0002] ( E )-Alkenyl sulfone compounds have many good biological activities and are often used as potent inhibitors of enzymatic processes, such as VCAM-1 expression inhibitors, cysteine ​​protease inhibitors, HIV-1 integrase inhibitors, etc. also,( E )-alkenyl sulfone compounds, as an important organic structural building block, also have a wide range of applications in organic synthetic chemistry, for example, alkenyl sulfone compounds can be used as acceptors for Michael addition reactions, and can also be used as important for D-A reactions. raw material. Li's group reported that CuI or Cu / Fe synergistic di-tert-butyl peroxide (DTBP) was used as a catalyst to prepare aromatic alkynes or aromatic alkyne acids with sulfonyl hydrazides at 100 °C ( E )-alkenyl sulfones in moderate yie...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C315/00C07C317/14C07C317/22
CPCC07C315/00C07C407/00C07C2601/14C07C317/14C07C317/22C07C409/04C07C409/14C07C409/08
Inventor 张宝华史兰香
Owner SHIJIAZHUANG UNIVERSITY