2-(adamantan-1-yl)propanenitrile | 790248-36-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(adamantan-1-yl)propanenitrile
• 英文别名: 2-(1-adamantyl)propanenitrile
• CAS: 790248-36-1
• 化学式: C₁₃H₁₉N
• 分子量: 189.301
• InChiKey: CFVRENFYMWLAOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(adamantan-1-yl)propanenitrile 、 叔丁基二甲基氯硅烷 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 12.08h， 以83%的产率得到N-(2-(adamantan-1-yl)prop-1-en-1-ylidene)-1-(tert-butyl)-1,1-dimethylsilanamine
  参考文献：
  名称：

  Catalytic Asymmetric Protonation of Silyl Ketene Imines

  摘要：

  An efficient catalytic and highly enantioselective protonation of silyl ketene imines is described. The reaction is catalyzed by the chiral phosphoric acids TRIP or STRIP in the presence of a stoichiometric amount of methanol as the proton source and silyl acceptor. A variety of substituted racemic silyl ketene imines have been transformed into highly enantioenriched nitriles.

  DOI：

  10.1021/ja312141b
• 作为产物：
  描述：

  1,3-脱氢金刚烷 、 丙腈 以 乙醚 为溶剂， 反应 8.0h， 以82%的产率得到2-(adamantan-1-yl)propanenitrile
  参考文献：
  名称：

  Adamantylation of carbonitriles with 1,3-dehydroadamantane and its homologs

  摘要：

  1,3-Dehydroadamantane and its methyl-substituted homologs react with carbonitriles at the alpha-carbon atom of the latter to give the corresponding alpha-adamantyl carbonitriles. This reaction provide a convenient one-step procedure for selective synthesis of branched nitriles which are difficult to obtain by traditional procedures.

  DOI：

  10.1134/s1070428014090085

文献信息

• Catalytic Asymmetric Protonation of Silyl Ketene Imines
  作者：Joyram Guin、Georgy Varseev、Benjamin List

  DOI：10.1021/ja312141b

  日期：2013.2.13

  An efficient catalytic and highly enantioselective protonation of silyl ketene imines is described. The reaction is catalyzed by the chiral phosphoric acids TRIP or STRIP in the presence of a stoichiometric amount of methanol as the proton source and silyl acceptor. A variety of substituted racemic silyl ketene imines have been transformed into highly enantioenriched nitriles.
• Adamantylation of carbonitriles with 1,3-dehydroadamantane and its homologs
  作者：V. M. Mokhov、G. M. Butov

  DOI：10.1134/s1070428014090085

  日期：2014.9

  1,3-Dehydroadamantane and its methyl-substituted homologs react with carbonitriles at the alpha-carbon atom of the latter to give the corresponding alpha-adamantyl carbonitriles. This reaction provide a convenient one-step procedure for selective synthesis of branched nitriles which are difficult to obtain by traditional procedures.