3-methyl-3-<(trimethylsilyl)oxy>butyronitrile | 14904-41-7

• 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-methyl-3-<(trimethylsilyl)oxy>butyronitrile
• 英文别名: 3-Methyl-3-(trimethylsiloxy)butanenittile；3-methyl-3-(trimethylsiloxy)butanenitrile；3,3-Dimethyl-3-trimethylsiloxy-propionitril；3-Methyl-3-((trimethylsilyl)oxy)butanenitrile；3-methyl-3-trimethylsilyloxybutanenitrile
• CAS: 14904-41-7
• 化学式: C₈H₁₇NOSi
• 分子量: 171.315
• InChiKey: DBUVYXFBFZDAOQ-UHFFFAOYSA-N

物化性质

• 沸点：
  199.5±13.0 °C(Predicted)
• 密度：
  0.873±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  11
• 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

• 作为产物：
  描述：

  甲基环氧丙烷 、 三甲基氰硅烷 在 氯化二乙基铝 作用下， 反应 48.0h， 以52%的产率得到3-methyl-3-<(trimethylsilyl)oxy>butyronitrile
  参考文献：
  名称：

  Regiospecificity of reactions of epoxides and oxetanes with trimethylsilyl cyanide

  摘要：

  DOI：

  10.1021/jo00136a011

文献信息

• Monosodium acetonitriles, their preparation, properties and reactions
  作者：Carl Krüger

  DOI：10.1016/s0022-328x(00)92412-4

  日期：1967.7

  Monosodium acetonitrile and homologous compounds are prepared by the reaction of sodium bis(trimethylsilyl)amide with acetonitrile or the corresponding nitriles in either solution at low temperature. The IR and NMR spectra of these compounds are discussed. Sodium acetonitrile adds to polar double bonds (carbonyl and cyano groups) only. It is shown that sodium acetonitrile and analogous compounds are

  通过双（三甲基甲硅烷基）酰胺钠与乙腈或相应的腈在任何一种溶液中在低温下反应，制得乙腈单钠盐和同源化合物。讨论了这些化合物的IR和NMR光谱。乙腈钠仅加到极性双键（羰基和氰基）上。已表明乙腈和类似化合物是腈与烯胺的缩合反应的中间体。乙腈钠最好是在氰化物受体存在下充当卡宾生成器。
• 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。
• Sugita, Keisuke; Ohta, Akihisa; Onaka, Makoto, Chemistry Letters, 1990, # 3, p. 481 - 484
  作者：Sugita, Keisuke、Ohta, Akihisa、Onaka, Makoto、Izumi, Yusuke

  DOI：——

  日期：——
• Reaction of cyanotrimethylsilane with oxiranes. Effects of catalysts or mediators on regioselectivity and ambident character
  作者：Katsuharu Imi、Naoto Yanagihara、Kiitiro Utimoto

  DOI：10.1021/jo00382a008

  日期：1987.3
• Regiospecificity of reactions of epoxides and oxetanes with trimethylsilyl cyanide
  作者：Jeffrey C. Mullis、William P. Weber

  DOI：10.1021/jo00136a011

  日期：1982.7