(Z)-N-(but-2-ynyl)-N-(4-chlorobut-2-enyl)-4-methylbenzenesulfonamide | 1234505-52-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-N-(but-2-ynyl)-N-(4-chlorobut-2-enyl)-4-methylbenzenesulfonamide
• 英文别名: N-but-2-ynyl-N-[(Z)-4-chlorobut-2-enyl]-4-methylbenzenesulfonamide
• CAS: 1234505-52-2
• 化学式: C₁₅H₁₈ClNO₂S
• 分子量: 311.832
• InChiKey: TWUPTHQZBPUJRS-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-N-(but-2-ynyl)-N-(4-chlorobut-2-enyl)-4-methylbenzenesulfonamide 在 silver hexafluoroantimonate 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 1,4-双(二苯基膦)丁烷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以82%的产率得到(E)-3-(1-chloroethylidene)-1-tosyl-4-vinylpyrrolidine
  参考文献：
  名称：

  Rhodium-catalyzed synthesis of γ-butyrolactams and pyrrolidines via cycloisomerization of N-tethered 1,6-enynes

  摘要：

  A rhodium-catalyzed cycloisomerization reaction of N-tethered 1,6-enynes with an intramolecular halogen shift has been developed, providing a useful process for the synthesis of stereo defined gamma-butyrolactam and pyrrolidine derivatives in good to excellent yields. Effects of both electronic feature and steric structure of the substrates on the outcome of the reaction were investigated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.097
• 作为产物：
  描述：

  顺式-1,4-二氯-2-丁烯 、 4-methyl-N-(prop-1-yn-1-yl)benzenesulfonamide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以52%的产率得到(Z)-N-(but-2-ynyl)-N-(4-chlorobut-2-enyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Rhodium-catalyzed synthesis of γ-butyrolactams and pyrrolidines via cycloisomerization of N-tethered 1,6-enynes

  摘要：

  A rhodium-catalyzed cycloisomerization reaction of N-tethered 1,6-enynes with an intramolecular halogen shift has been developed, providing a useful process for the synthesis of stereo defined gamma-butyrolactam and pyrrolidine derivatives in good to excellent yields. Effects of both electronic feature and steric structure of the substrates on the outcome of the reaction were investigated. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.097

文献信息

• Rhodium-catalyzed synthesis of γ-butyrolactams and pyrrolidines via cycloisomerization of N-tethered 1,6-enynes
  作者：Jianping Wang、Xiaomin Xie、Fangfang Ma、Zhiyong Peng、Lei Zhang、Zhaoguo Zhang

  DOI：10.1016/j.tet.2010.03.097

  日期：2010.6

  A rhodium-catalyzed cycloisomerization reaction of N-tethered 1,6-enynes with an intramolecular halogen shift has been developed, providing a useful process for the synthesis of stereo defined gamma-butyrolactam and pyrrolidine derivatives in good to excellent yields. Effects of both electronic feature and steric structure of the substrates on the outcome of the reaction were investigated. (C) 2010 Elsevier Ltd. All rights reserved.