(+/-)-trans-1-acetoxy-2-phthalimidocyclohexane | 1491151-40-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (+/-)-trans-1-acetoxy-2-phthalimidocyclohexane
• 英文别名: (1R,2R)-trans-2-phthalimido-1-acetoxycyclohexane
• CAS: 1491151-40-6
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: XEAVISFFLUIAGN-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (+/-)-trans-1-acetoxy-2-phthalimidocyclohexane 在 Arthrobacter sp. lipase 、 水 、 一水合肼 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 (1R,2R)-(-)-2-氨基环己醇
  参考文献：
  名称：

  Cyclic trans-β-amino alcohols: preparation and enzymatic kinetic resolution

  摘要：

  Enantioenriched cyclic beta-amino alcohols, trans-2-aminocyclohexanols (ee, > 99%), trans-2-aminocyclopentanols (ee, > 99%), trans-1-amino-2-indanols (ee, > 99%) and trans-2-amino-1-indanols (ee, similar to 98%) were prepared in high yields via an Arthrobacter sp. Lipase/PLAP catalyzed kinetic resolution of racemic phthalimido acetates. The addition of toluene as a co-solvent dramatically improved the hydrolysis and enantioselectivity, whereas for indanols, substrate immobilization on Celite improved the efficacy of the kinetic resolution. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.019
• 作为产物：
  描述：

  苯酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 (+/-)-trans-1-acetoxy-2-phthalimidocyclohexane
  参考文献：
  名称：

  Cyclic trans-β-amino alcohols: preparation and enzymatic kinetic resolution

  摘要：

  Enantioenriched cyclic beta-amino alcohols, trans-2-aminocyclohexanols (ee, > 99%), trans-2-aminocyclopentanols (ee, > 99%), trans-1-amino-2-indanols (ee, > 99%) and trans-2-amino-1-indanols (ee, similar to 98%) were prepared in high yields via an Arthrobacter sp. Lipase/PLAP catalyzed kinetic resolution of racemic phthalimido acetates. The addition of toluene as a co-solvent dramatically improved the hydrolysis and enantioselectivity, whereas for indanols, substrate immobilization on Celite improved the efficacy of the kinetic resolution. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.019

文献信息

• Enzymatic transesterification of pharmacologically interesting β-aminocycloalkanol precursors
  作者：Javier González-Sabín、Nicolás Ríos-Lombardía、Vicente Gotor、Francisco Morís

  DOI：10.1016/j.tetasy.2013.08.007

  日期：2013.11

  Chemoenzymatic syntheses of both enantiomers of cis- and trans-2-aminocyclopentanol as well as cis- and trans-2-aminocyclohexanol, which are valuable building blocks for a plethora of ligands and pharmaceuticals have been efficiently carried out. The strategy involves the stereospecific syntheses of racemic aminocycloalkanol precursors via tagging of a phthalimide as a masking group and subsequent lipase-catalyzed kinetic resolution. Most of the lipases exhibited excellent enantioselectivity (E >> 200) in the transesterification reactions of trans-derivatives, with both N-protected (R,R)-amino acetates and (S,S)-amino alcohols being isolated in enantiopure form. With regard to cis-derivatives, lipases were also very selective, even though the biotransformations were significantly slower. (C) 2013 Elsevier Ltd. All rights reserved.