N-[(1S,2R)-2-hydroxymethylcyclohexyl]benzamide | 203064-42-0

• 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: N-[(1S,2R)-2-hydroxymethylcyclohexyl]benzamide
• 英文别名: N-Benzoyl-cis-2-hydroxymethylcyclohexylamin；N-[(1S,2R)-2-(hydroxymethyl)cyclohexyl]benzamide
• CAS: 203064-42-0
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: SBVMITIYFLLAQQ-STQMWFEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[(1S,2R)-2-hydroxymethylcyclohexyl]benzamide 在 盐酸 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 106.5h， 生成 (1S,2R)-2-甲基环己胺
  参考文献：
  名称：

  Rational de novo design of NADH mimic for stereoselective reduction based on molecular orbital calculation

  摘要：

  The methodology of rational design of NADH mimics in stereoselective reduction of carbonyl and imino groups based on molecular orbital calculation was described. The designed NADH mimics la and Ib were subjected to the reduction of benzoylformate and acetyliminophenylacetate. As expected from the calculations of the transition-states, the reduction with la proceeded with high stereoselectivity in both substrates, while Ib showed much lower chirality transfer. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10294-0
• 作为产物：
  描述：

  (-)-顺式-2-苄胺基环己基羧酸 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.5h， 生成 N-[(1S,2R)-2-hydroxymethylcyclohexyl]benzamide
  参考文献：
  名称：

  Rational de novo design of NADH mimic for stereoselective reduction based on molecular orbital calculation

  摘要：

  The methodology of rational design of NADH mimics in stereoselective reduction of carbonyl and imino groups based on molecular orbital calculation was described. The designed NADH mimics la and Ib were subjected to the reduction of benzoylformate and acetyliminophenylacetate. As expected from the calculations of the transition-states, the reduction with la proceeded with high stereoselectivity in both substrates, while Ib showed much lower chirality transfer. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10294-0