(E)-1,1,1-trimethyl-N-(3-phenyl-2-propenyl)-N-(trimethylsilyl)silanamine | 124582-74-7

• 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: (E)-1,1,1-trimethyl-N-(3-phenyl-2-propenyl)-N-(trimethylsilyl)silanamine
• 英文别名: N,N-Bis(trimethylsiyl)cinnamylamine；(E)-3-phenyl-N,N-bis(trimethylsilyl)prop-2-en-1-amine
• CAS: 124582-74-7
• 化学式: C₁₅H₂₇NSi₂
• 分子量: 277.557
• InChiKey: ZQKXFFIHKKAJCA-JLHYYAGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1,1,1-trimethyl-N-(3-phenyl-2-propenyl)-N-(trimethylsilyl)silanamine 在 盐酸 作用下， 以 甲苯 为溶剂， 生成 肉桂基胺
  参考文献：
  名称：

  由1-三丁基锡烷基-3-双（三甲基甲硅烷基）氨基丙-1-烯简单合成伯E-烯丙基胺

  摘要：

  通过使用乙烯基锡基的直接钯催化偶联或通过转化为γ-氨基乙烯基锂试剂，从容易获得的γ-氨基乙烯基锡试剂2中描述了一种简便且选择性的伯E-烯丙基胺的制备方法。

  DOI：

  10.1016/s0040-4039(00)79880-7
• 作为产物：
  描述：

  肉桂基氯 、 lithium hexamethyldisilazane 在 silver(I) iodide 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以59%的产率得到(E)-1,1,1-trimethyl-N-(3-phenyl-2-propenyl)-N-(trimethylsilyl)silanamine
  参考文献：
  名称：

  烯丙基氯化物与碘化银/ N，N-二甲硅烷基酰胺混合试剂的胺化反应

  摘要：

  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。

  DOI：

  10.1039/c39900000789

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。
• A simple synthesis of primary E-allylic amines from 1-tributylstannyl-3-bis(trimethylsilyl)amino prop-1-ene
  作者：Robert J.P. Corriu、Geng Bolin、Joël J.E. Moreau

  DOI：10.1016/s0040-4039(00)79880-7

  日期：1991.8

  A facile and selective preparation of primary E-allylic amines is described from the readily available γ-amino vinylic tin reagent 2, either by using the direct palladium catalysed coupling of the vinyl tin moitie or via conversion to a γ-amino vinyl lithium reagent.

  通过使用乙烯基锡基的直接钯催化偶联或通过转化为γ-氨基乙烯基锂试剂，从容易获得的γ-氨基乙烯基锡试剂2中描述了一种简便且选择性的伯E-烯丙基胺的制备方法。
• Cobalt carbonyl catalyzed hydrosilylation of nitriles: a new preparation of N,N-disilylamines
  作者：Toshiaki Murai、Takehiko Sakane、Shinzi Kato

  DOI：10.1021/jo00289a014

  日期：1990.1
• 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：——
• 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.