N-[(4-fluorophenyl)-trimethylsilylmethyl]-N-methylnitrous amide | 256658-43-2

• 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: N-[(4-fluorophenyl)-trimethylsilylmethyl]-N-methylnitrous amide
• CAS: 256658-43-2
• 化学式: C₁₁H₁₇FN₂OSi
• 分子量: 240.353
• InChiKey: IYQYWCBYYKQHFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  丁炔二酸二甲酯 、 N-[(4-fluorophenyl)-trimethylsilylmethyl]-N-methylnitrous amide 以 甲苯 为溶剂， 反应 1.0h， 以88%的产率得到5-(4-Fluoro-phenyl)-1-methyl-1H-pyrazole-3,4-dicarboxylic acid dimethyl ester
  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：

  (4-氟苯基)甲基三甲基硅烷 在 N-溴代丁二酰亚胺(NBS) 、 sodium nitrite 作用下， 以 甲醇 、 四氯化碳 为溶剂， 生成 N-[(4-fluorophenyl)-trimethylsilylmethyl]-N-methylnitrous 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.