(5aR,9aS)-Octahydro-benzo[e][1,3,2]dioxathiepine 3,3-dioxide | 174152-13-7

• 英文名称: (5aR,9aS)-Octahydro-benzo[e][1,3,2]dioxathiepine 3,3-dioxide
• CAS: 174152-13-7
• 化学式: C₈H₁₄O₄S
• 分子量: 206.263
• InChiKey: IZOQUTLQUZLEHF-OCAPTIKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.08
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (5aR,9aS)-Octahydro-benzo[e][1,3,2]dioxathiepine 3,3-dioxide 在 硫酸 作用下， 反应 13.5h， 生成 (+)-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：

  cis-1,2-cyclohexanedimethanol 在 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 、 三乙胺 作用下， 生成 (5aR,9aS)-Octahydro-benzo[e][1,3,2]dioxathiepine 3,3-dioxide
  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