benzyl (2R,3aR,7aR)-octahydroindole-2-carboxylate | 760916-37-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: benzyl (2R,3aR,7aR)-octahydroindole-2-carboxylate
• 英文别名: benzyl (2R,3aR,7aR)-2,3,3a,4,5,6,7,7a-octahydro-1H-indole-2-carboxylate
• CAS: 760916-37-8
• 化学式: C₁₆H₂₁NO₂
• 分子量: 259.348
• InChiKey: ARGCRCXTJMQKNA-RBSFLKMASA-N

物化性质

• 沸点：
  376.3±25.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  benzyl (2R,3aR,7aR)-octahydroindole-2-carboxylate 、 二碳酸二叔丁酯 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 以81%的产率得到benzyl (2R,3aR,7aR)-N-(tert-butoxycarbonyl)octahydroindole-2-carboxylate
  参考文献：
  名称：

  Efficient access to enantiomerically pure cyclic α-amino esters through a lipase-catalyzed kinetic resolution

  摘要：

  A series of alpha-amino acid derivatives containing the 2,3-dihydroindole or octahydroindole core have been chemoenzymatically synthesized in good overall yields and high enantiomeric purity under mild reaction conditions using lipases for the introduction of chirality. Candida antarctica lipase type A has shown excellent activity and high enantiodiscrimination ability toward the two cyclic amino esters used as substrates. The selectivity of the process proved to be greatly dependent on the alkoxycarbonylating agent. Thus, the enzymatic kinetic resolution of methyl indoline-2-carboxylate has been successfully achieved using 3-methoxyphenyl allyl carbonate, whereas (2R,3aR,7aR)-benzyl octahydroindole-2-carboxylate required the less reactive diallyl carbonate. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.010
• 作为产物：
  描述：

  碳酸二稀丙酯 、 (2S,3aS,7aS)-八氢-1H-吲哚-2-羧酸苯甲酯 在 IMB-104 Candida antarctica lipase A 作用下， 以 various solvent(s) 为溶剂， 反应 72.0h， 以91%的产率得到benzyl (2S,3aS,7aS)-N-(allyloxycarbonyl)-octahydroindole-2-carboxylate
  参考文献：
  名称：

  Efficient access to enantiomerically pure cyclic α-amino esters through a lipase-catalyzed kinetic resolution

  摘要：

  A series of alpha-amino acid derivatives containing the 2,3-dihydroindole or octahydroindole core have been chemoenzymatically synthesized in good overall yields and high enantiomeric purity under mild reaction conditions using lipases for the introduction of chirality. Candida antarctica lipase type A has shown excellent activity and high enantiodiscrimination ability toward the two cyclic amino esters used as substrates. The selectivity of the process proved to be greatly dependent on the alkoxycarbonylating agent. Thus, the enzymatic kinetic resolution of methyl indoline-2-carboxylate has been successfully achieved using 3-methoxyphenyl allyl carbonate, whereas (2R,3aR,7aR)-benzyl octahydroindole-2-carboxylate required the less reactive diallyl carbonate. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.010

文献信息

• Novel method for preparation of crystalline perindopril erbumine
  申请人：Singh Pal Girij

  公开号：US20070149604A1

  公开（公告）日：2007-06-28

  A process for preparation of crystalline perindopril erbumine of formula (II) which exhibits the X-ray (powder) diffraction pattern like that shown in FIG. 2 The process comprises reacting a solution of perindopril of formula (I), in a solvent selected from N,N-dimethylformamide, dimethyl acetals of lower aliphatic aldehydes, dimethyl ketals of lower aliphatic ketones and 1,2-dialkoxyethane with tertiary butylamine and crystallization of the erbumine salt thus obtained by heating the reaction mixture to reflux, filtering hot, cooling gradually to 20° C. to 30° C., and further cooling to 0° C. to 15° C. for 30 minutes to 1 hour and finally filtering off and drying the crystals.

  一种制备式（II）晶体型的依普利酸厄贝林的方法，其展现出类似于图2所示的X射线（粉末）衍射图谱。该方法包括在从N,N-二甲基甲酰胺、低级脂肪醛的二甲基缩醛、低级脂肪酮的二甲基缩酮和1,2-二烷氧基乙烷中选择的溶剂中反应式（I）的依普利酸溶液，与叔丁胺反应，并通过将反应混合物加热至回流，过滤热，逐渐冷却至20°C至30°C，然后进一步冷却至0°C至15°C，保持30分钟至1小时，最后过滤并干燥晶体来结晶得到厄贝林盐。
• US7456296B2
  申请人：——

  公开号：US7456296B2

  公开（公告）日：2008-11-25
• US7521566B2
  申请人：——

  公开号：US7521566B2

  公开（公告）日：2009-04-21
• Efficient access to enantiomerically pure cyclic α-amino esters through a lipase-catalyzed kinetic resolution
  作者：Sergio Alatorre-Santamaría、María Rodriguez-Mata、Vicente Gotor-Fernández、Marcos Carlos de Mattos、Francisco J. Sayago、Ana I. Jiménez、Carlos Cativiela、Vicente Gotor

  DOI：10.1016/j.tetasy.2008.06.010

  日期：2008.7

  A series of alpha-amino acid derivatives containing the 2,3-dihydroindole or octahydroindole core have been chemoenzymatically synthesized in good overall yields and high enantiomeric purity under mild reaction conditions using lipases for the introduction of chirality. Candida antarctica lipase type A has shown excellent activity and high enantiodiscrimination ability toward the two cyclic amino esters used as substrates. The selectivity of the process proved to be greatly dependent on the alkoxycarbonylating agent. Thus, the enzymatic kinetic resolution of methyl indoline-2-carboxylate has been successfully achieved using 3-methoxyphenyl allyl carbonate, whereas (2R,3aR,7aR)-benzyl octahydroindole-2-carboxylate required the less reactive diallyl carbonate. (C) 2008 Elsevier Ltd. All rights reserved.