(Z)-2,3-bis(trimethylsilylmethyl)-6-(pyrrolidin-1-yl)hex-2-enenitrile | 1236131-34-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (Z)-2,3-bis(trimethylsilylmethyl)-6-(pyrrolidin-1-yl)hex-2-enenitrile
• 英文别名: (Z)-6-pyrrolidin-1-yl-2,3-bis(trimethylsilylmethyl)hex-2-enenitrile
• CAS: 1236131-34-2
• 化学式: C₁₈H₃₆N₂Si₂
• 分子量: 336.668
• InChiKey: LXKZFEWODUIZIA-ZCXUNETKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.36
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-吡咯烷基丁腈 、 1,4-bis(trimethylsilyl)-2-butyne 在 bis(1,5-cyclooctadiene)nickel (0) 、 三(2-甲氧基苯基)膦 、 三甲基铝 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 5.0h， 以94%的产率得到(Z)-2,3-bis(trimethylsilylmethyl)-6-(pyrrolidin-1-yl)hex-2-enenitrile
  参考文献：
  名称：

  Heteroatom-Directed Alkylcyanation of Alkynes

  摘要：

  Alkanenitriles having a heteroatom such as nitrogen, oxygen, and sulfur at the gamma-position are found to add across alkynes stereo- and regioselectively by nickel/Lewis acid catalysis to give highly substituted acrylonitriles. The heteroatom functionalities likely coordinate to the nickel center to make oxidative addition of the C-CN bonds of the alkyl cyanides kinetically favorable, forming a five-membered nickelacycle intermediate and, thus, preventing beta-hydride elimination to allow the alkylcyanation reaction.

  DOI：

  10.1021/ja1017078

文献信息

• Heteroatom-Directed Alkylcyanation of Alkynes
  作者：Yoshiaki Nakao、Akira Yada、Tamejiro Hiyama

  DOI：10.1021/ja1017078

  日期：2010.7.28

  Alkanenitriles having a heteroatom such as nitrogen, oxygen, and sulfur at the gamma-position are found to add across alkynes stereo- and regioselectively by nickel/Lewis acid catalysis to give highly substituted acrylonitriles. The heteroatom functionalities likely coordinate to the nickel center to make oxidative addition of the C-CN bonds of the alkyl cyanides kinetically favorable, forming a five-membered nickelacycle intermediate and, thus, preventing beta-hydride elimination to allow the alkylcyanation reaction.