N-methyl-N-(trimethylsilylmethyl)nitrous amide | 256658-45-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-methyl-N-(trimethylsilylmethyl)nitrous amide
• CAS: 256658-45-4
• 化学式: C₅H₁₄N₂OSi
• 分子量: 146.264
• InChiKey: KHFIJVKREBBERS-UHFFFAOYSA-N

物化性质

• 沸点：
  197.0±23.0 °C(Predicted)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.48
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苯乙炔 、 N-methyl-N-(trimethylsilylmethyl)nitrous amide 以 甲苯 为溶剂， 反应 1.0h， 以11%的产率得到1-甲基-3-苯基-吡唑
  参考文献：
  名称：

  Novel generation of azomethine imines from α-silylnitrosamines by 1,4-silatropic shift and their cycloaddition

  摘要：

  Novel and facile generation of azomethine imines from alpha-silylnitrosamines and subsequent cycloaddition with dipolarophiles leading to a variety of pyrazole derivatives have been developed. The key to the reaction is a 1,4-silatropic shift caused by strong affinity of the nitroso oxygen atom toward the silicon atom. Thus, alpha-silylnitrosamines are treated with 1 equiv. of dipolarophiles in refluxing toluene for 1 h to give pyrazole derivatives in good to excellent yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01859-6
• 作为产物：
  描述：

  三甲基氯硅烷 、 亚硝基二甲胺 在 lithium diisopropyl amide 作用下， 生成 N-methyl-N-(trimethylsilylmethyl)nitrous amide
  参考文献：
  名称：

  Novel generation of azomethine imines from α-silylnitrosamines by 1,4-silatropic shift and their cycloaddition

  摘要：

  Novel and facile generation of azomethine imines from alpha-silylnitrosamines and subsequent cycloaddition with dipolarophiles leading to a variety of pyrazole derivatives have been developed. The key to the reaction is a 1,4-silatropic shift caused by strong affinity of the nitroso oxygen atom toward the silicon atom. Thus, alpha-silylnitrosamines are treated with 1 equiv. of dipolarophiles in refluxing toluene for 1 h to give pyrazole derivatives in good to excellent yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01859-6

文献信息

• Novel generation of azomethine imines from α-silylnitrosamines by 1,4-silatropic shift and their cycloaddition
  作者：Ken-Ichi Washizuka、Keiko Nagai、Satoshi Minakata、Ilhyong Ryu、Mitsuo Komatsu

  DOI：10.1016/s0040-4039(99)01859-6

  日期：1999.12

  Novel and facile generation of azomethine imines from alpha-silylnitrosamines and subsequent cycloaddition with dipolarophiles leading to a variety of pyrazole derivatives have been developed. The key to the reaction is a 1,4-silatropic shift caused by strong affinity of the nitroso oxygen atom toward the silicon atom. Thus, alpha-silylnitrosamines are treated with 1 equiv. of dipolarophiles in refluxing toluene for 1 h to give pyrazole derivatives in good to excellent yields. (C) 1999 Elsevier Science Ltd. All rights reserved.