[(1S,2R)-2-(diethoxyphosphorylmethyl)cyclohexyl]methyl acetate | 174152-14-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: [(1S,2R)-2-(diethoxyphosphorylmethyl)cyclohexyl]methyl acetate
• CAS: 174152-14-8
• 化学式: C₁₄H₂₇O₅P
• 分子量: 306.339
• InChiKey: MOQMBKJTWJLINC-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  Acetic acid (1S,6R)-6-(diethoxy-phosphorylmethyl)-cyclohex-3-enylmethyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 10.0h， 生成 [(1S,2R)-2-(diethoxyphosphorylmethyl)cyclohexyl]methyl acetate
  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