(E)-2-phenylhex-4-ene-1,2-diol | 182509-79-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-2-phenylhex-4-ene-1,2-diol
• CAS: 182509-79-1
• 化学式: C₁₂H₁₆O₂
• 分子量: 192.258
• InChiKey: WWXAEOYOYJFSLG-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-2-phenylhex-4-ene-1,2-diol 在 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 2-(4-chlorophenyl)pent-4-ene-1,2-diol
  参考文献：
  名称：

  Lipase AKG mediated resolutions of α,α-disubstituted 1,2-diols in organic solvents; remarkably high regio- and enantio-selectivity

  摘要：

  Diols 1, which contain adjacent tertiary and primary hydroxy groups, can be selectively mono-acylated at the primary hydroxy group by many lipases in organic solvents, Since the reaction does not take place at the chiral tertiary centre itself, observed enantioselectivities are usually low. Only the combination of one lipase, lipase AKG (Amano, Pseudomonas sp.), with selected substrates gives high enantioselectivities (E 20 to > 200), Also, the solvent and acyl donor employed influences the outcome, On the basis of the results of Lipase AKG towards substrates 1 an active site model for this specific lipase has been developed, which can account for the results obtained, Fu!! experimental details on the synthesis of diols 1 and enzymatic preparation of acetates 2 are given, Also, the absolute stereochemistry of the enzymatically prepared diols 1 has been established by independent synthesis from (R)-mandelic acid.

  DOI：

  10.1039/p19960002051
• 作为产物：
  描述：

  2,2-二甲基-5-苯基-1,3-二氧杂烷-4-酮 在 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 (E)-2-phenylhex-4-ene-1,2-diol
  参考文献：
  名称：

  Lipase AKG mediated resolutions of α,α-disubstituted 1,2-diols in organic solvents; remarkably high regio- and enantio-selectivity

  摘要：

  Diols 1, which contain adjacent tertiary and primary hydroxy groups, can be selectively mono-acylated at the primary hydroxy group by many lipases in organic solvents, Since the reaction does not take place at the chiral tertiary centre itself, observed enantioselectivities are usually low. Only the combination of one lipase, lipase AKG (Amano, Pseudomonas sp.), with selected substrates gives high enantioselectivities (E 20 to > 200), Also, the solvent and acyl donor employed influences the outcome, On the basis of the results of Lipase AKG towards substrates 1 an active site model for this specific lipase has been developed, which can account for the results obtained, Fu!! experimental details on the synthesis of diols 1 and enzymatic preparation of acetates 2 are given, Also, the absolute stereochemistry of the enzymatically prepared diols 1 has been established by independent synthesis from (R)-mandelic acid.

  DOI：

  10.1039/p19960002051

文献信息

• Lipase AKG mediated resolutions of α,α-disubstituted 1,2-diols in organic solvents; remarkably high regio- and enantio-selectivity
  作者：Robert P. Hof、Richard M. Kellogg

  DOI：10.1039/p19960002051

  日期：——

  Diols 1, which contain adjacent tertiary and primary hydroxy groups, can be selectively mono-acylated at the primary hydroxy group by many lipases in organic solvents, Since the reaction does not take place at the chiral tertiary centre itself, observed enantioselectivities are usually low. Only the combination of one lipase, lipase AKG (Amano, Pseudomonas sp.), with selected substrates gives high enantioselectivities (E 20 to > 200), Also, the solvent and acyl donor employed influences the outcome, On the basis of the results of Lipase AKG towards substrates 1 an active site model for this specific lipase has been developed, which can account for the results obtained, Fu!! experimental details on the synthesis of diols 1 and enzymatic preparation of acetates 2 are given, Also, the absolute stereochemistry of the enzymatically prepared diols 1 has been established by independent synthesis from (R)-mandelic acid.