2-(trimethylsiloxy)-2-(trimethylsilyl)propanenitrile | 53173-08-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 2-(trimethylsiloxy)-2-(trimethylsilyl)propanenitrile
• 英文别名: 2-(Trimethylsilyl)-2-[(trimethylsilyl)oxy]propanenitrile；2-trimethylsilyl-2-trimethylsilyloxypropanenitrile
• CAS: 53173-08-3
• 化学式: C₉H₂₁NOSi₂
• 分子量: 215.443
• InChiKey: KZRPSLLRUDMFLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(trimethylsiloxy)-2-(trimethylsilyl)propanenitrile 在 盐酸 作用下， 以 乙醚 为溶剂， 以83%的产率得到2-Hydroxy-2-(trimethylsilyl)propanenitrile
  参考文献：
  名称：

  The metalation-silylation of O-trimethylsilyl aldehyde cyanohydrins

  摘要：

  The metalation-trimethylsilyation of O-trimethylsilyl (saturated) aldehyde cyanohydrins was achieved by in situ treatment with LDA and trimethylchlorosilane at -78-degrees-C. C-Silyl products (O-trimethylsilyl acylsilane cyanohydrins) generally predominated, but N-silyl derivatives (ketenimines) were found in some instances. LDA could be added across the C = N bond of the latter. The metalation-trimethylsilylation of O-trimethylsilyl benzaldehyde cyanohydrin could only be effected if 2 equiv of trimethylchlorosilane were employed per equivalent of cyanohydrin anion.

  DOI：

  10.1021/jo00030a030
• 作为产物：
  描述：

  三甲基氰硅烷 、 1-(trimethylsilyl)ethanone 在 吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 生成 2-(trimethylsiloxy)-2-(trimethylsilyl)propanenitrile
  参考文献：
  名称：

  Acetylsilane O-silylcyanohydrins as precursors to .alpha.-silyl ketones and .beta.-siloxy-N,N-bissilylenamines

  摘要：

  DOI：

  10.1021/jo00302a029

文献信息

• A preparation of N,N-bis(trimethylsilyl)allenamines
  作者：Robert F. Cunico、Chia P. Kuan

  DOI：10.1016/0022-328x(94)05068-m

  日期：1995.2

  elimination of 2-[N,N-bis(trimethylsilyl)amino]alkenyl (diethyl)phosphates affords 1-[N,N-bis(trimethylsilyl)amino]-1,2-alkadienes (“allenamines”). Conjugatively-substituted allenamines undergo further metalation under these eliminative conditions to form allenyl carbanions which may be trapped in situ by chlorotrimethylsilane to give 3-trimethylsilyl-or 3,3-bis(trimethylsilyl)-N,N-bis(trimethylsilyl)allenamines

  二异丙基氨基锂诱导的2- [ N，N-双（三甲基甲硅烷基）氨基]链烯基（二乙基）磷酸酯的消除得到1- [ N，N-双（三甲基甲硅烷基）氨基] -1,2-链二烯（“亚胺基”） 。在这些消除条件下，共轭取代的烯丙胺进一步金属化，形成烯丙基碳负离子，这些碳烯基碳负离子可以被氯三甲基硅烷原位捕获，得到3-三甲基甲硅烷基-或3,3-双（三甲基甲硅烷基）-N，N-双（三甲基甲硅烷基）亚烷基胺。
• Synthesis of oxazoles from O-trimethylsilyl acyltrimethylsilane cyanohydrins
  作者：Robert F. Cunico、Chia P. Kuan

  DOI：10.1021/jo00038a020

  日期：1992.6

  Sequential addition of organolithium reagents and acyl chlorides (or anhydrides) to O-trimethylsilyl acyltrimethylsilane cyanohydrins affords beta-(acyloxy)-N,N-bis(trimethylsilyl) enamines which cyclize to substituted oxazoles under thermolysis or treatment with trimethylsilyl trifluoromethanesulfonate. Oxazoles were prepared containing alkyl and phenyl substituents at C-5, alkyl, alkenyl, and phenyl substituents at C-4, and alkyl, alkenyl, phenyl, and functionalized substituents at C-2.
• New anionic rearrangements. XVII. 1,2-Anionic rearrangements from oxygen to carbon in benzyloxyorganosilanes and benzyloxyorganogermanes
  作者：Antony Wright、Robert West

  DOI：10.1021/ja00817a030

  日期：1974.5
• Oxazoles from β-acyloxy-n,n-bis(trimethylsilyl)enamines
  作者：Robert F. Cunico、Chia P. Kuan

  DOI：10.1016/s0040-4039(00)88885-1

  日期：1990.1
• CUNICO, ROBERT F.;KUAN, CHIA P., TETRAHEDRON LETT., 31,(1990) N4, C. 1945-1948
  作者：CUNICO, ROBERT F.、KUAN, CHIA P.

  DOI：——

  日期：——