2-(Trimethylsilyl)-2-<(trimethylsilyl)oxy>ethanenitrile | 129601-09-8

• 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-(Trimethylsilyl)-2-<(trimethylsilyl)oxy>ethanenitrile
• 英文别名: Trimethylsilyl(trimethylsiloxy)acetonitril；2-Trimethylsilyl-2-trimethylsilyloxyacetonitrile
• CAS: 129601-09-8
• 化学式: C₈H₁₉NOSi₂
• 分子量: 201.416
• InChiKey: DRWMIGBRCPXJOT-UHFFFAOYSA-N

物化性质

• 沸点：
  81 °C(Press: 18 Torr)
• 密度：
  0.867±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  碘甲基三甲基硅烷 、 2-(Trimethylsilyl)-2-<(trimethylsilyl)oxy>ethanenitrile 在 四甲基乙二胺 、 lithium diethylamide 作用下， 生成 2,3-Bis(trimethylsilyl)-2-<(trimethylsilyl)oxy>propanenitrile
  参考文献：
  名称：

  Metalation-alkylation of O-trimethylsilyl formyltrimethylsilane cyanohydrin in the synthesis of oxazoles

  摘要：

  DOI：

  10.1021/jo00051a064
• 作为产物：
  描述：

  三甲基氯硅烷 、 2-<(Trimethylsilyl)oxy>ethanenitrile 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到2-(Trimethylsilyl)-2-<(trimethylsilyl)oxy>ethanenitrile
  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

文献信息

• Transformation of α-assisted carbanions into the corresponding trimethylsiloxy derivatives using bis(trimethylsilyl)peroxide
  作者：P. Dembech、A. Guerrini、A. Ricci、G. Seconi、M. Taddei

  DOI：10.1016/s0040-4020(01)88391-5

  日期：1990.1

  The reaction of bis(trimethylsilyl)peroxide with tlithium derivatives of sulphides and nitriles is reported to give the corresponding O-trimethylsilyl hemithioacetals and cyanohydrins. From these products the carbonyl function can be exposed in acidic media or in the presence of fluoride ions. This methodology provides an attractive route to transform a CH2-X group (X = PhS, MeS or CN) into the corresponding

  据报道，双（三甲基甲硅烷基）过氧化物与硫化物和腈的锂衍生物反应生成相应的O-三甲基甲硅烷基半硫缩醛和氰醇。从这些产物中，羰基官能团可以在酸性介质中或在氟离子存在下暴露。这种方法学提供了一种有吸引力的途径，可以将CH 2 -X基团（X = PhS，MeS或CN）转化为相应的CHO，从而可以制备认为难以制备的醛，例如生成的甲酰基三甲基硅烷并使用维蒂希反应原位捕获。
• 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.
• DEMBECH, P.;GUERRINI, A.;RICCI, A.;SECONI, G.;TADDEI, M., TETRAHEDRON, 46,(1990) N, C. 2999-3006
  作者：DEMBECH, P.、GUERRINI, A.、RICCI, A.、SECONI, G.、TADDEI, M.

  DOI：——

  日期：——
• The metalation-silylation of O-trimethylsilyl aldehyde cyanohydrins
  作者：Robert F. Cunico、Chia P. Kuan

  DOI：10.1021/jo00030a030

  日期：1992.2

  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.
• Metalation-alkylation of O-trimethylsilyl formyltrimethylsilane cyanohydrin in the synthesis of oxazoles
  作者：Robert F. Cunico、Chia P. Kuan

  DOI：10.1021/jo00051a064

  日期：1992.12