3-(Trimethyl)siloxynonanenitrile | 125945-82-6

• 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: 3-(Trimethyl)siloxynonanenitrile
• 英文别名: 3-Trimethylsilyloxynonanenitrile
• CAS: 125945-82-6
• 化学式: C₁₂H₂₅NOSi
• 分子量: 227.422
• InChiKey: MFEONMZKQAZUNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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 、 1,2-环氧辛烷 在 calcium fluoride 作用下， 以 正庚烷 为溶剂， 反应 72.0h， 生成 3-(Trimethyl)siloxynonanenitrile
  参考文献：
  名称：

  Sugita, Keisuke; Ohta, Akihisa; Onaka, Makoto, Chemistry Letters, 1990, # 3, p. 481 - 484

  摘要：

  DOI：

文献信息

• Regiospecific Ring Opening of Epoxides with Cyanotrimethylsilane on Solid Bases: Reaction Features, and Role of Metal Cations of Solid Bases
  作者：Keisuke Sugita、Akihisa Ohta、Makoto Onaka、Yusuke Izumi

  DOI：10.1246/bcsj.64.1792

  日期：1991.6

  A new attempt of utilizing solid acids and bases for ring opening of epoxides with Me3SiCN was investigated. Solid strong bases such as calcium oxide and magnesium oxide catalyzed the regio- and chemoselective ring opening of epoxides with Me3SiCN much more effectively than homogeneous catalysts. On CaO and MgO, the reactions of unsymmetrical epoxides with Me3SiCN afforded 3-trimethylsiloxyalkanenitriles in high yields through regio- and stereoselective attack of cyanide ion on the less substituted epoxycarbon. Additionally, on CaO, 2,3-epoxy-1-alkanol derivatives were selectively converted to the corresponding C-3 opened products by the attack of cyanide ion. In these cases no isocyanides were formed. It was suggested that CaO acted as a bifunctional catalyst; the lattice oxide anions of CaO activated Me3SiCN, and simultaneously calcium ions promoted the ring opening of epoxyalkanol as Lewis acid sites.

  利用固态酸和碱进行环氧化物与Me3SiCN开环反应的新尝试已被研究。与均相催化剂相比，固态强碱如氧化钙和氧化镁能更有效地催化环氧化物与Me3SiCN的区域选择性和化学选择性开环反应。在氧化钙和氧化镁存在下，不对称环氧化物与Me3SiCN的反应通过氰离子对次级环氧碳的区域和立体选择性攻击，高产率地生成了3-三甲基硅氧基烷腈。此外，在氧化钙存在下，2,3-环氧-1-醇衍生物被氰离子选择性地转化为相应的C-3开环产物，且未形成异氰化物。研究提出，氧化钙作为一种双功能催化剂，其晶格氧化物阴离子活化Me3SiCN，同时钙离子作为路易斯酸位点促进环氧醇的开环反应。
• 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.
• Reaction of cyanotrimethylsilane with oxiranes under Yb(CN)3 catalysis
  作者：Seijiro Matsubara、Hitoshi Onishi、Kiitiro Utimoto

  DOI：10.1016/s0040-4039(00)97026-6

  日期：1990.1
• MATSUBARA, SEIJIRO;ONISHI, HITOSHI;UTIMOTO, KIITIRO, TETRAHEDRON LETT., 31,(1990) N3, C. 6209-6212
  作者：MATSUBARA, SEIJIRO、ONISHI, HITOSHI、UTIMOTO, KIITIRO

  DOI：——

  日期：——