(Z)-2-Benzenesulfinyl-3-phenyl-acrylic acid | 213193-38-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-2-Benzenesulfinyl-3-phenyl-acrylic acid
• 英文别名: (Z)-2-(benzenesulfinyl)-3-phenylprop-2-enoic acid
• CAS: 213193-38-5
• 化学式: C₁₅H₁₂O₃S
• 分子量: 272.324
• InChiKey: HDTYRQHYUHQFHH-KAMYIIQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  73.6
• 氢给体数：
  1
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	Z-3-phenyl-2-(phenylthio)propenoic acid	58808-67-6	C15H12O2S	256.325

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  Z-3-苯基-2-(苯基磺酰基)丙烯酸	Z-3-phenyl-2-(phenylsulfonyl)propenoic acid	213193-39-6	C15H12O4S	288.324
  ——	(Z)-2-Benzenesulfinyl-3-phenyl-acryloyl chloride	213193-45-4	C15H11ClO2S	290.77
  ——	Z-3-phenyl-2-(phenylsulfonyl)propenoyl chloride	213193-51-2	C15H11ClO3S	306.77

反应信息

• 作为反应物：
  描述：

  (Z)-2-Benzenesulfinyl-3-phenyl-acrylic acid 在 Oxone 、 草酰氯 作用下， 以 1,4-二氧六环 、 氘代氯仿 、 水 为溶剂， 反应 5.0h， 生成 Z-3-phenyl-2-(phenylsulfonyl)propenoyl chloride
  参考文献：
  名称：

  Activated Michael Acceptors as Precursors to Heterocycles. 1. 2-Azetidinones from 2-(Arylsulfonyl)propenoyl Chlorides and Amines

  摘要：

  The addition of NH3 and other primary amines to Z-3-phenyl-2-(arylsulfonyl)propenoyl chlorides gives trans-2-arylsulfonyl-3-phenyl-2-azetidinones as the major product in addition to the corresponding 2-arylsulfonyl-3-phenylpropenamide. Electron-withdrawing substituents in the arylsulfonyl group increased the percentage of products derived from 1,4-addition relative to 1,2-addition, while electron-donating substituents increased the amount of 1,2-addition observed in the product mixture. Addition of alpha-methylbenzylamine gave a 68:32 mixture of the two diastereomers of the trans-azetidinone. The major diastereomer was identified as the 1-(1R)-(3S,4S) and 1-(1S)-(3R,4R) enantiomers 16a by single-crystal X-ray crystallographic analysis, Phenylthio and phenylsulfoxo substituents did not promote 1,4-addition, although the addition of ammonia to Z-3-phenyl-2-(phenylsulfoxo)propenoyl chloride (7a) gave a 95:5 ratio of the corresponding propenamide 8a and a 3-(phenylsulfoxo)azetidinone 9a. trans-4-Phenyl-3-(arylsulfonyl)-2-azetidinones 12a and 12c were sulfonated by the pyridine-SO3 complex to give the corresponding N-sulfonates 28 in > 80% yield. The p-methoxybenzyl substituent of 15 was removed by eerie ammonium nitrate in CH3CN to give 12a in 70% yield.

  DOI：

  10.1021/jo980234p
• 作为产物：
  描述：

  Z-3-phenyl-2-(phenylthio)propenoic acid 在 sodium tungstate 、 双氧水 作用下， 反应 15.0h， 以86%的产率得到(Z)-2-Benzenesulfinyl-3-phenyl-acrylic acid
  参考文献：
  名称：

  Activated Michael Acceptors as Precursors to Heterocycles. 1. 2-Azetidinones from 2-(Arylsulfonyl)propenoyl Chlorides and Amines

  摘要：

  The addition of NH3 and other primary amines to Z-3-phenyl-2-(arylsulfonyl)propenoyl chlorides gives trans-2-arylsulfonyl-3-phenyl-2-azetidinones as the major product in addition to the corresponding 2-arylsulfonyl-3-phenylpropenamide. Electron-withdrawing substituents in the arylsulfonyl group increased the percentage of products derived from 1,4-addition relative to 1,2-addition, while electron-donating substituents increased the amount of 1,2-addition observed in the product mixture. Addition of alpha-methylbenzylamine gave a 68:32 mixture of the two diastereomers of the trans-azetidinone. The major diastereomer was identified as the 1-(1R)-(3S,4S) and 1-(1S)-(3R,4R) enantiomers 16a by single-crystal X-ray crystallographic analysis, Phenylthio and phenylsulfoxo substituents did not promote 1,4-addition, although the addition of ammonia to Z-3-phenyl-2-(phenylsulfoxo)propenoyl chloride (7a) gave a 95:5 ratio of the corresponding propenamide 8a and a 3-(phenylsulfoxo)azetidinone 9a. trans-4-Phenyl-3-(arylsulfonyl)-2-azetidinones 12a and 12c were sulfonated by the pyridine-SO3 complex to give the corresponding N-sulfonates 28 in > 80% yield. The p-methoxybenzyl substituent of 15 was removed by eerie ammonium nitrate in CH3CN to give 12a in 70% yield.

  DOI：

  10.1021/jo980234p

文献信息

• Activated Michael Acceptors as Precursors to Heterocycles. 1. 2-Azetidinones from 2-(Arylsulfonyl)propenoyl Chlorides and Amines
  作者：Feng Zhou、Jonathan Rosen、Jennifer M. Zebrowski-Young、Patricia M. Freihammer、Michael R. Detty、Rene J. Lachicotte

  DOI：10.1021/jo980234p

  日期：1998.8.1

  The addition of NH3 and other primary amines to Z-3-phenyl-2-(arylsulfonyl)propenoyl chlorides gives trans-2-arylsulfonyl-3-phenyl-2-azetidinones as the major product in addition to the corresponding 2-arylsulfonyl-3-phenylpropenamide. Electron-withdrawing substituents in the arylsulfonyl group increased the percentage of products derived from 1,4-addition relative to 1,2-addition, while electron-donating substituents increased the amount of 1,2-addition observed in the product mixture. Addition of alpha-methylbenzylamine gave a 68:32 mixture of the two diastereomers of the trans-azetidinone. The major diastereomer was identified as the 1-(1R)-(3S,4S) and 1-(1S)-(3R,4R) enantiomers 16a by single-crystal X-ray crystallographic analysis, Phenylthio and phenylsulfoxo substituents did not promote 1,4-addition, although the addition of ammonia to Z-3-phenyl-2-(phenylsulfoxo)propenoyl chloride (7a) gave a 95:5 ratio of the corresponding propenamide 8a and a 3-(phenylsulfoxo)azetidinone 9a. trans-4-Phenyl-3-(arylsulfonyl)-2-azetidinones 12a and 12c were sulfonated by the pyridine-SO3 complex to give the corresponding N-sulfonates 28 in > 80% yield. The p-methoxybenzyl substituent of 15 was removed by eerie ammonium nitrate in CH3CN to give 12a in 70% yield.