(-)-cis-1-(diethylphosphono)methyl-2-hydroxymethylcyclohexane

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (-)-cis-1-(diethylphosphono)methyl-2-hydroxymethylcyclohexane
• 英文别名: [(1S,2R)-2-(diethoxyphosphorylmethyl)cyclohexyl]methanol
• 化学式: C₁₂H₂₅O₄P
• 分子量: 264.302
• InChiKey: NSQWSLKMELUKCT-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-cis-1-(diethylphosphono)methyl-2-hydroxymethylcyclohexane 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (1R,2S)-2-diethylphosphonomethylcyclohexane-1-carboxyaldehyde
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of cis-1-diethylphosphonomethyl-2-hydroxymethylcyclohexane. Application to enantioselective synthesis of 1-diethylphosphonomethyl-2-(5′-hydantoinyl)cyclohexane

  摘要：

  A kinetic resolution of cis-1-diethylphosphonomethyl-2-hydroxymethylcyclohexane 1 by lipase has been developed. The transesterification of (+/-)-1 with vinyl acetate in the presence of Lipase AK without solvent proceeded to give (+)-1 and the corresponding acetate (+)-5 in good yield and high enantiomeric ratio. The alcohol (+)-1 was transformed to the optically active hydantoins 12 and 13, possible intermediates for the synthesis of conformational constrained analogues of AP-5.

  DOI：

  10.1016/0957-4166(95)00403-3
• 作为产物：
  描述：

  [(1S,2R)-2-(diethoxyphosphorylmethyl)cyclohexyl]methyl acetate 在 甲醇 、 氨 作用下， 反应 48.0h， 以58%的产率得到(-)-cis-1-(diethylphosphono)methyl-2-hydroxymethylcyclohexane
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of cis-1-diethylphosphonomethyl-2-hydroxymethylcyclohexane. Application to enantioselective synthesis of 1-diethylphosphonomethyl-2-(5′-hydantoinyl)cyclohexane

  摘要：

  A kinetic resolution of cis-1-diethylphosphonomethyl-2-hydroxymethylcyclohexane 1 by lipase has been developed. The transesterification of (+/-)-1 with vinyl acetate in the presence of Lipase AK without solvent proceeded to give (+)-1 and the corresponding acetate (+)-5 in good yield and high enantiomeric ratio. The alcohol (+)-1 was transformed to the optically active hydantoins 12 and 13, possible intermediates for the synthesis of conformational constrained analogues of AP-5.

  DOI：

  10.1016/0957-4166(95)00403-3

文献信息

• Lipase-catalyzed kinetic resolution of cis-1-diethylphosphonomethyl-2-hydroxymethylcyclohexane. Application to enantioselective synthesis of 1-diethylphosphonomethyl-2-(5′-hydantoinyl)cyclohexane
  作者：Tsutomu Yokomatsu、Nobuko Nakabayashi、Keita Matsumoto、Shiroshi Shibuya

  DOI：10.1016/0957-4166(95)00403-3

  日期：1995.12

  A kinetic resolution of cis-1-diethylphosphonomethyl-2-hydroxymethylcyclohexane 1 by lipase has been developed. The transesterification of (+/-)-1 with vinyl acetate in the presence of Lipase AK without solvent proceeded to give (+)-1 and the corresponding acetate (+)-5 in good yield and high enantiomeric ratio. The alcohol (+)-1 was transformed to the optically active hydantoins 12 and 13, possible intermediates for the synthesis of conformational constrained analogues of AP-5.