(Z)-2-(3-methylphenyl)sulfonyl-3-phenylprop-2-enoic acid | 213193-85-2

• 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-(3-methylphenyl)sulfonyl-3-phenylprop-2-enoic acid
• CAS: 213193-85-2
• 化学式: C₁₆H₁₄O₄S
• 分子量: 302.351
• InChiKey: ULYFENYYCFZCEB-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  79.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (Z)-2-(3-methylphenyl)sulfonyl-3-phenylprop-2-enoic acid 在 ammonium hydroxide 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 氘代氯仿 、 二氯甲烷 为溶剂， 反应 1.0h， 生成
  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)-2-(3-methylphenyl)sulfinyl-3-phenylprop-2-enoic acid 在 Oxone 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.0h， 生成 (Z)-2-(3-methylphenyl)sulfonyl-3-phenylprop-2-enoic 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.