3-bis(trimethylsilyl)amino-2-methyl-1-trimethylsilylpropene | 129762-97-6

• 英文名称: 3-bis(trimethylsilyl)amino-2-methyl-1-trimethylsilylpropene
• 英文别名: (Z)-N,N,3-Tris(trimethylsilyl)-2-methyl-2-propen-1-amine；(Z)-1--(2-methyl)vinyltrimethylsilane；(Z)-2-methyl-N,N,3-tris(trimethylsilyl)prop-2-en-1-amine
• CAS: 129762-97-6
• 化学式: C₁₃H₃₃NSi₃
• 分子量: 287.668
• InChiKey: LVWQUDANUNAFFL-SEYXRHQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  3-trimethylsilylamino-1-methylpropene 在 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 36.0h， 生成 3-bis(trimethylsilyl)amino-2-methyl-1-trimethylsilylpropene
  参考文献：
  名称：

  有机合成中的甲硅烷基胺：N，C-二硫代甲硅烷基胺的制备和一些反应

  摘要：

  已经研究了一些烯烃和芳族N-三甲基甲硅烷基胺的双金属化。用二摩尔比例的正丁基锂处理得到有机二金属试剂，其与三甲基氯硅烷反应以45％至65％的产率得到N，N，C-三（三甲基甲硅烷基）胺。由（三甲基甲硅烷基）（烯丙基）胺获得的二元试剂与苯甲酰氯，N，N-二甲基甲酰胺，-2-呋喃甲酸乙酯和苯甲react反应，得到取代的吡咯和吡啶。

  DOI：

  10.1016/s0022-328x(00)99805-x

文献信息

• Amination reaction of allylic chlorides with silver iodide/lithium N,N-disilylamide mixed reagents
  作者：Toshiaki Murai、Mikio Yamamoto、Shinzi Kato

  DOI：10.1039/c39900000789

  日期：——

  The nucleophilic substitution of allylic chlorides with silver iodide/lithium N,N-disilylamide mixed reagents gives protected primary allylic amines in good to excellent yields.

  用碘化银/ N，N-二甲硅烷基酰胺混合试剂对烯丙基氯化物进行亲核取代，可以良好或极好的收率得到受保护的伯烯丙基胺。
• Silver iodide mediated amination reaction of allylic chlorides with lithium bis(trimethylsilyl)amide: a new synthetic method of N,N-disilylallylamines via lithium amide argentates
  作者：Toshiaki Murai、Mikio Yamamoto、Shigeru Kondo、Shinzi Kato

  DOI：10.1021/jo00078a024

  日期：1993.12

  The nucleophilic substitution reaction of allylic chlorides with lithium bis(trimethylsilyl)amide (1) in the presence of silver halides has been studied in detail. Silver iodide (AgI) was found to be most effective for facilitation of the amination reaction. The reaction of alkyl-substituted allylic chlorides proceeded smoothly in S(N)2 fashion to give N,N-disilylallylamines in high yields when 0.1 or 0.5 equiv of AgI was used as an additive, whereas a stoichiometric amount of AgI was indispensable in the reaction of allylic chlorides having a phenyl group. The reaction of geranyl or neryl chloride proceeded with retention of configuration of the C=C bond to give only one isomer 4 or 5, respectively. The oxygen-containing functional groups and chlorine remained intact during the reaction. The reaction of alpha-silylmetallyl chloride 17 proceeded in an S(N)2' manner to afford (Z)-allylamine 18. So as to disclose the active species in the AgI-mediated reaction, the variable low-temperature C-13 NMR experiments using the mixture of AgI and 1 in THF have been performed. It has been suggested that lithium amide argentates such as (Me3Si)2NAg(I)Li (20) and [(Me3Si)2N]2Ag(I)Li2 (21) are formed in the reaction mixture, and the nucleophilicity and basicity of 1 are controlled by forming these species.
• MURAI, TOSHIAKI;YAMAMOTO, MIKIO;KATO, SHINZI, J. CHEM. SOC. CHEM. COMMUN.,(1990) N1, C. 789-790
  作者：MURAI, TOSHIAKI、YAMAMOTO, MIKIO、KATO, SHINZI

  DOI：——

  日期：——