4-phenyl-1-trimethylsilanyloxy-cyclohexanecarbonitri;e | 516484-49-4

• 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: 4-phenyl-1-trimethylsilanyloxy-cyclohexanecarbonitri;e
• 英文别名: 1-trimethylsilyloxy-1-(4'-phenylcyclohexyl)-1-carbonitrile；Cyclohexanecarbonitrile, 4-phenyl-1-[(trimethylsilyl)oxy]-；4-phenyl-1-trimethylsilyloxycyclohexane-1-carbonitrile
• CAS: 516484-49-4
• 化学式: C₁₆H₂₃NOSi
• 分子量: 273.45
• InChiKey: YYQUZZFRBYNMBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三甲基氰硅烷 、 4-苯基环己酮 在 N,N-二甲基苯胺氧化物 、 三乙基铝 、 N,N'-bis(3,5-di-tert-butylsalicylidene)ethylenediamine 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 11.0h， 以97%的产率得到4-phenyl-1-trimethylsilanyloxy-cyclohexanecarbonitri;e
  参考文献：
  名称：

  Highly Efficient Double-Activation Catalysts for the Synthesis of Ketone Cyanohydrins

  摘要：

  在无溶剂的环境温度下，使用沙仑-铝络合物（0.25 摩尔%）和 N-氧化物（0.5 摩尔%）合成了叔氰醇三甲基硅醚，化学收率极高。讨论了配体结构与催化剂效率之间的关系。进行了初步的机理研究，并提出了双活化催化剂作用的过渡态。

  DOI：

  10.1055/s-2004-831167

文献信息

• Cyanosilylation of Ketones Catalyzed by Quaternary Ammonium Salt and<i>N</i>-Oxide
  作者：Xiaoming Feng、Hui Zhou、Fu-Xue Chen、Bo Qin、Guolin Zhang

  DOI：10.1055/s-2004-820045

  日期：——

  Dibenzyldimethyl ammonium bromide and triethanol­amine N-oxide catalyze the formation of cyanohydrin trimethylsilyl ethers of ketones in 80-99% yield.

  二苄基二甲基溴化铵和三乙醇胺 N-氧化物可催化生成氰醇三甲基硅醚酮，产率为 80-99%。
• Dodecatungestophosphoric acid (H3PW12O40) as a solid green BrØnsted acid catalyzes high yielding and efficient trimethylcyanosylilation reactions of aldehydes and ketones by trimethylsilyl cyanide
  作者：Habib Firouzabadi、Nasser Iranpoor、Abbas Ali Jafari

  DOI：10.1016/j.jorganchem.2004.12.025

  日期：2005.3

  An efficient solvent-free method is described for the addition of TMSCN to carbonyl groups employing dodecatungestophosphoric acid (H3PW12O40) as a heterogeneous and environmentally benign catalyst. By this method, aromatic, aliphatic, cyclic and heterocyclic aldehydes and ketones are converted into their corresponding cyanotrimethylsilyl ethers in excellent yields (89-98%) in short reaction times (< 10 min). (c) 2004 Published by Elsevier B.V.
• Iodine as novel reagent for the 1,2-addition of trimethylsilyl cyanide to ketones including α,β-unsaturated ketones
  作者：J.S. Yadav、B.V.S. Reddy、M.Sridhar Reddy、A.R. Prasad

  DOI：10.1016/s0040-4039(02)02321-3

  日期：2002.12

  Molecular iodine is found to catalyze efficiently the addition of trimethylsilyl cyanide to a range of simple and functionalized ketones under very mild and convenient conditions to afford the corresponding cyanohydrin trimethylsilyl ethers in excellent yields in a short reaction period with high selectivity. a,P-Unsaturated ketones selectively afford the corresponding 1,2-adducts without the formation of 1,4-adducts under similar reaction conditions. (C) 2002 Elsevier Science Ltd. All rights reserved.
• A Highly Efficient and Recyclable Silica-Based Scandium(III) Interphase Catalyst for Cyanosilylation of Carbonyl Compounds
  作者：Babak Karimi、Leila Ma'Mani

  DOI：10.1021/ol0482083

  日期：2004.12.1

  A new silica-based scandium(III) interphase catalyst 2 efficiently catalyzes the cyanosilylation of a variety of aldehydes and ketones. The catalyst shows high thermal stability (up to 300degreesC) and also is stable in both organic and polar solvents. It also could be recovered and reused for at least 10 reaction cycles without considerable loss of reactivity.
• Chen, Fuxue; Feng, Xiaoming; Qin, Bo, Synlett, 2003, # 4, p. 558 - 560
  作者：Chen, Fuxue、Feng, Xiaoming、Qin, Bo、Zhang, Guolin、Jiang, Yaozhong

  DOI：——

  日期：——