1-cyano-2-trimethylsilyloxycyclohexane | 96101-62-1

• 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: 1-cyano-2-trimethylsilyloxycyclohexane
• 英文别名: (2-cyanocyclohexyloxy)trimethylsilane；O-(Trimethylsilyl)cyclohexanon-cyanhydrin；2-Trimethylsilyloxycyclohexane-1-carbonitrile
• CAS: 96101-62-1
• 化学式: C₁₀H₁₉NOSi
• 分子量: 197.352
• InChiKey: MOJPZIXGLYGBKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  249.7±33.0 °C(Predicted)
• 密度：
  0.92±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 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 、 氧化环己烯 在 Laponite-Yb 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以98%的产率得到1-cyano-2-trimethylsilyloxycyclohexane
  参考文献：
  名称：

  Scope and limitations of one-pot multistep reactions with heterogeneous catalysts: The case of alkene epoxidation coupled to epoxide ring-opening

  摘要：

  The combination of two reactions in one-pot multistep system requires the compatibility not only between the catalysts of both reactions, but also between all the reaction components and conditions. In the case of the coupling of alkene epoxidation and epoxide ring opening, it has been possible to synthesize cyanohydrin and azidohydrin derivatives through a simple process that involves a one-pot multistep process by using a mixture of two heterogeneous catalysts, a silica-grafted Ti catalyst and ytterbium chloride, whose efficiency depends on the reactivity of the starting alkene. In addition, in some cases the mixture of catalysts can be recovered and reused in several one-pot multistep cycles. However, this system is not possible with electron- deficient alkenes, as the basic catalyst required for epoxidation has shown to be incompatible with the ring-opening process. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cattod.2011.03.067

文献信息

• Tetraaryl-1,3-dioxolane-4,5-dimethanols as catalysts for the addition of trimethylsilyl cyanide to benzaldehyde and the oxirane ring
  作者：Yu. N. Belokon’、V. I. Maleev、Z. T. Gugkaeva、M. A. Moskalenko、A. T. Tsaloev、A. S. Peregudov、S. Ch. Gagieva、K. A. Lyssenko、V. N. Khrustalev、A. V. Grachev

  DOI：10.1007/s11172-007-0233-7

  日期：2007.8

  The synthesis of 1,2-, 1,3-, and 1,4-phenylene-bis[(4R,5R)-4,5-di(hydroxydiphenylmethyl)-1,3-dioxolane]s (ortho-, meta-, and para-bis-(R,R)-TADDOLs) and bis[4-[(4R, 5R)-4,5-di(hydroxydiphenylmethyl)]-1,3-dioxolan-2-yl}phenyl]methane was carried out. The possibilities of the use of these compounds as catalysts for the C-C bond formation in the addition of Me3SiCN to benzaldehyde and the oxirane ring opening in cyclohexene oxide by Me3SiCN were investigated. The catalytic activity of different bis-(R, R)-TADDOLs in this series depends on their structure.

  研究人员合成了 1,2-、1,3-和 1,4-亚苯基双[(4R,5R)-4,5-二(羟基二苯基甲基)-1,3-二氧戊环]（正、偏和对位双双(R,R)-TADDOLs）和双[4-[(4R,5R)-4,5-二(羟基二苯基甲基)]-1,3-二氧戊环-2-基}苯基]甲烷。研究了这些化合物作为催化剂在 Me3SiCN 与苯甲醛的加成反应中形成 C-C 键以及 Me3SiCN 在环己烯氧化物中开启环氧乙烷环的可能性。该系列中不同双（R，R）-TADDOL 的催化活性取决于它们的结构。
• Asymmetric meso-Epoxide Ring-Opening with Trimethylsilyl Cyanide Promoted by Chiral Binuclear Complexes of Titanium. Dichotomy of CC versus CN Bond Formation
  作者：Yuri N. Belokon、Denis Chusov、Alexander S. Peregudov、Lidia V. Yashkina、Galina I. Timofeeva、Victor I. Maleev、Michael North、Henri B. Kagan

  DOI：10.1002/adsc.200900523

  日期：2009.12

  In the presence of chiral catalysts derived from the same chiral hexadentate ligand and aluminium, zinc or titanium ions, the reaction between cyclohexene oxide and trimethylsilyl cyanide can be controlled to give predominantly either the nitrile (up to 99% ee) or the isonitrile product (up to 94% ee). The metal ion, ligand stereochemistry and base concentration all play a role in determining the product

  在衍生自相同手性六齿配体和铝，锌或钛离子的手性催化剂存在的情况下，可以控制环己烯氧化物与三甲基甲硅烷基氰化物之间的反应，从而主要生成腈（至多为99％ee）或异腈产物（高达94％ee）。金属离子，配体立体化学和碱浓度均在确定产物比率中起作用。
• Lidy,W.; Sundermeyer,W., Chemische Berichte, 1973, vol. 106, p. 587 - 593
  作者：Lidy,W.、Sundermeyer,W.

  DOI：——

  日期：——
• Lakshmi Kantam; Choudary; Bharathi, Synthetic Communications, 1999, vol. 29, # 7, p. 1121 - 1128
  作者：Lakshmi Kantam、Choudary、Bharathi

  DOI：——

  日期：——
• Scope and limitations of one-pot multistep reactions with heterogeneous catalysts: The case of alkene epoxidation coupled to epoxide ring-opening
  作者：José M. Fraile、Nuria García、Clara I. Herrerías、José A. Mayoral

  DOI：10.1016/j.cattod.2011.03.067

  日期：2011.9

  The combination of two reactions in one-pot multistep system requires the compatibility not only between the catalysts of both reactions, but also between all the reaction components and conditions. In the case of the coupling of alkene epoxidation and epoxide ring opening, it has been possible to synthesize cyanohydrin and azidohydrin derivatives through a simple process that involves a one-pot multistep process by using a mixture of two heterogeneous catalysts, a silica-grafted Ti catalyst and ytterbium chloride, whose efficiency depends on the reactivity of the starting alkene. In addition, in some cases the mixture of catalysts can be recovered and reused in several one-pot multistep cycles. However, this system is not possible with electron- deficient alkenes, as the basic catalyst required for epoxidation has shown to be incompatible with the ring-opening process. (C) 2011 Elsevier B.V. All rights reserved.