(1R,2S)-N-(2-phenylcyclohexyl)methoxyacetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2S)-N-(2-phenylcyclohexyl)methoxyacetamide
• 英文别名: 2-methoxy-N-[(1R,2S)-2-phenylcyclohexyl]acetamide
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: NMHQZFLDJUIDFC-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-苯基环己酮 在 钯 甲酸 、 Novozyme 435 immobilized on polyacrylamide 、 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 78.0h， 生成 (1R,2S)-N-(2-phenylcyclohexyl)methoxyacetamide
  参考文献：
  名称：

  Enantioselective acylation of rac-2-phenylcycloalkanamines catalyzed by lipases

  摘要：

  The kinetic resolution of some 2-phenylcycloalkanamines was performed by means of aminolysis reactions catalyzed by lipases, with Kazlauskas' rule being obeyed in all cases. The size of the ring and the stereochemistry of the stereogenic centers of the amines had a strong influence on both the enantiomeric ratio and the reaction rate of these aminolysis processes. Lipase B from Candida antarctica (CAL-B) showed excellent enantio selectivities toward trans-2-phenylcyclohexanamine in a variety of reaction conditions (E > 150), whereas lipase A from C antarctica (CAL-A) was the best catalyst for the acylation of cis-2-phenylcyclohexanamine (E = 34) and trans-2-phenylcyclopropanamine (E = 9). (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.033

文献信息

• Enantioselective acylation of rac-2-phenylcycloalkanamines catalyzed by lipases
  作者：Javier González-Sabín、Vicente Gotor、Francisca Rebolledo

  DOI：10.1016/j.tetasy.2005.07.033

  日期：2005.9

  The kinetic resolution of some 2-phenylcycloalkanamines was performed by means of aminolysis reactions catalyzed by lipases, with Kazlauskas' rule being obeyed in all cases. The size of the ring and the stereochemistry of the stereogenic centers of the amines had a strong influence on both the enantiomeric ratio and the reaction rate of these aminolysis processes. Lipase B from Candida antarctica (CAL-B) showed excellent enantio selectivities toward trans-2-phenylcyclohexanamine in a variety of reaction conditions (E > 150), whereas lipase A from C antarctica (CAL-A) was the best catalyst for the acylation of cis-2-phenylcyclohexanamine (E = 34) and trans-2-phenylcyclopropanamine (E = 9). (C) 2005 Elsevier Ltd. All rights reserved.