(S)-2-(adamantan-1-yl)propanenitrile | 1421692-33-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-2-(adamantan-1-yl)propanenitrile
• 英文别名: (2S)-2-(1-adamantyl)propanenitrile
• CAS: 1421692-33-2
• 化学式: C₁₃H₁₉N
• 分子量: 189.301
• InChiKey: CFVRENFYMWLAOB-HIVKSXORSA-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

• 作为产物：
  描述：

  1-金刚烷乙睛 在 正丁基锂 、 (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 甲苯 、 正戊烷 为溶剂， 反应 26.08h， 生成 (S)-2-(adamantan-1-yl)propanenitrile 、 (R)-2-(adamantan-1-yl)propanenitrile
  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

文献信息

• [EN] A PROCESS FOR INDUSTRIAL PREPARATION OF [(S)-N-TERT BUTOXYCARBONYL-3-HYDROXY]ADAMANTYLGLYCINE<br/>[FR] PROCÉDÉ DE PRÉPARATION INDUSTRIELLE DE LA [(S)-N-TERT BUTOXYCARBONYL-3-HYDROXY]ADAMANTYLGLYCINE
  申请人：LEE PHARMA LTD

  公开号：WO2014057495A1

  公开（公告）日：2014-04-17

  A commercially viable process for industrial preparation of [(S)-n-tert butoxycarbonyl-3-hydroxy]adamantylglycine which is a key intermediate for saxagliptin synthesis and is represented by compound of Formula-VI. The compound-VI obtained by the process of present invention has more than 99.5% HPLC purity, not more than 0.15 % of dihydroxy impurity, not more than 0.05% of isomer impurity and not more than 0.1% of any unknown impurity. Formula (VI).

  一种工业制备[(S)-n-叔丁氧羰基-3-羟基]金刚烷基甘氨酸的商业可行过程，该物质是撒格列普汀合成的关键中间体，代表化合物的结构式为VI。本发明的工艺获得的化合物VI具有超过99.5%的HPLC纯度，不超过0.15%的二羟基杂质，不超过0.05%的异构体杂质和不超过0.1%的任何未知杂质。结构式（VI）。
• 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.