(1R,2S)-cis-2-phthalimido-1-acetoxycyclohexane | 1491151-39-3

• 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: (1R,2S)-cis-2-phthalimido-1-acetoxycyclohexane
• 英文别名: [(1R,2S)-2-(1,3-dioxoisoindol-2-yl)cyclohexyl] acetate
• CAS: 1491151-39-3
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: XEAVISFFLUIAGN-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-((1R,2R)-2-hydroxycyclohexyl)-1H-isoindole-1,3(2H)-dione 在 甲醇 、 lipase from Pseudomonas Cepacia 、 三苯基膦 、 sodium hydroxide 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲基叔丁基醚 为溶剂， 反应 72.0h， 生成 (±)-cis-2-phthalimidocyclohexanol 、 (1R,2S)-cis-2-phthalimido-1-acetoxycyclohexane
  参考文献：
  名称：

  Enzymatic transesterification of pharmacologically interesting β-aminocycloalkanol precursors

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2013.08.007