(-)-(1S,5R)-sobrerol | 137821-91-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-(1S,5R)-sobrerol
• CAS: 137821-91-1
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: DVQXSZLFASOBJB-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (-)-(1S,5R)-sobrerol 在 氢氧化钾 作用下， 以 甲醇 、 水 为溶剂， 以300 mg的产率得到反式-索布瑞醇
  参考文献：
  名称：

  Resolution of (±)-trans-sobrerol by lipase PS-catalyzed transesterification and effects of organic solvents on enantioselectivity

  摘要：

  Resolution of the mucolytic drug (+/-)-trans-sobrerol (1) was achieved by transesterification with vinyl acetate in organic media, catalyzed by free or immobilized Lipase PS. The enantioselectivity of the enzyme was markedly influenced by the nature of the organic solvent, but there was no correlation between enantiomeric ratio values (70-500) and either the hydrophobicity or the dielectric constant of the medium. With the enzyme immobilized onto Hyflo Super Cell and t-amyl alcohol as the solvent, the selectivity of Lipase PS for (-)-1 was extremely high and, at 50 % conversion both (-)-trans-sobrerol and (+)-trans-sobrerol monoacetate were obtained in practically 100 % optical purity.

  DOI：

  10.1016/s0957-4166(00)82205-3
• 作为产物：
  描述：

  反式-索布瑞醇 、 乙酸乙烯酯 在 lyophilized subtilisin 作用下， 以 四氢呋喃 为溶剂， 生成 (-)-(1S,5R)-sobrerol
  参考文献：
  名称：

  Application of structure-based thermodynamic calculations to the rationalization of the enantioselectivity of subtilisin in organic solvents

  摘要：

  The effect of organic solvents on the selectivity of lyophilized or CLEC (cross-linked enzyme crystals)-subtilisin in the resolution of sec-phenethyl alcohol and trans-sobrerol was studied. A theoretical model, that tries to predict solvent effects on enantioselectivity only as a function of the activity coefficients of the desolvated part of the substrate in the relevant transition state of the reaction (Ke, T.; Wescott, C. R.; Klibanov, A. M. J. Am. Chem. Sec., 1996, 118, 3366) was examined and shown to agree poorly with the experimental data. The tetrahedral intermediate was studied with MonteCarlo molecular mechanics, and the activity coefficients were calculated with UNIFAC. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00086-x