Z-3-phenyl-2-(phenylsulfonyl)propenoyl chloride | 213193-51-2

• 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-3-phenyl-2-(phenylsulfonyl)propenoyl chloride
• 英文别名: (Z)-2-(benzenesulfonyl)-3-phenylprop-2-enoyl chloride
• CAS: 213193-51-2
• 化学式: C₁₅H₁₁ClO₃S
• 分子量: 306.77
• InChiKey: LRKHZZOOFQOJIH-KAMYIIQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 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：
  59.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Z-3-phenyl-2-(phenylsulfonyl)propenoyl chloride 在 吡啶 、 氨 作用下， 以 二氯甲烷 为溶剂， 反应 22.5h， 生成 trans-N-(tert-butoxycarbonyl)-4-phenyl-3-(phenylsulfonyl)-2-azetidinone
  参考文献：
  名称：

  用N-卤代琥珀酰亚胺卤化4-苯基-3-（苯基磺酰基）-2-氮杂环丁酮。动力学与热力学控制。

  摘要：

  DOI：

  10.1021/jo000273c
• 作为产物：
  描述：

  Z-3-苯基-2-(苯基磺酰基)丙烯酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 氯仿 为溶剂， 反应 4.0h， 生成 Z-3-phenyl-2-(phenylsulfonyl)propenoyl chloride
  参考文献：
  名称：

  用N-卤代琥珀酰亚胺卤化4-苯基-3-（苯基磺酰基）-2-氮杂环丁酮。动力学与热力学控制。

  摘要：

  DOI：

  10.1021/jo000273c

文献信息

• A novel asymmetric synthesis of 2-azetidinones from achiral precursors
  作者：Feng Zhou、Michael R. Detty、Rene J. Lachicotte

  DOI：10.1016/s0040-4039(98)02473-3

  日期：1999.1

  Asymmetric synthesis of (3S,4S)-3-phenylsulfonyl-4-phenylazetidin-2-ones in up to 46% ee from achiral amines and 2-phenylsulfonyl-3-phenylpropenoyl chloride was achieved with chiral Lewis-acid catalysis by salen-copper(II) complexes derived from (1R,2R)-(−)-1,2-diaminocyclohexane. The absolute configuration was assigned by single crystal, X-ray crystallographic analysis of enantiomerically pure (3S

  由Salen手性路易斯酸催化，由非手性胺和2-苯基磺酰基-3-苯基丙烯酰基氯不对称合成（3 S，4 S）-3-苯基磺酰基-4-苯基氮杂环丁烷-2-酮的不对称合成率高达46％ee。衍生自（1 R，2 R）-（-）-1,2-二氨基环己烷的-铜（II）络合物。通过对映体纯的（3 S，4 S）-（-）-3-苯基磺酰基-4-苯基氮杂环丁烷-2-酮（7）的单晶X射线晶体学分析确定绝对构型。
• 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.