2-[(Z)-hept-1-enyl]propane-1,3-diol | 138436-16-5

• 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: 2-[(Z)-hept-1-enyl]propane-1,3-diol
• CAS: 138436-16-5
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: USDZXVPSEPAPRW-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.72
• 重原子数：
  12.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  乙酸乙烯酯 、 2-[(Z)-hept-1-enyl]propane-1,3-diol 在 3 A molecular sieve 作用下， 反应 15.0h， 生成 Acetic acid (Z)-(S)-2-hydroxymethyl-non-3-enyl ester
  参考文献：
  名称：

  Enzymatic asymmetrization of some prochiral and meso diols through monoacetylation with pig pancreatic lipase (PPL)

  摘要：

  Monoacetates 1-8 and 10-11, derived from asymmetric monoesterification of prochiral or meso diols, have been obtained in good to excellent enantiomeric excess by using inexpensive crude PPL supported on celite, and vinyl acetate as both solvent and acylating agent. Under these conditions reactions are fast and reproducible, and the enzyme can be recycled.

  DOI：

  10.1016/s0957-4166(00)80471-1
• 作为产物：
  描述：

  1-Acetoxy-2-(acetoxymethyl)non-3-yn-2-ol 在 palladium, 5% on calcium carbonate, poisoned with lead 2,6-二甲基吡啶 、 氢气 作用下， 以 乙醇 、 水 、 叔丁醇 为溶剂， 反应 7.0h， 生成 2-[(Z)-hept-1-enyl]propane-1,3-diol
  参考文献：
  名称：

  Chemoenzymic preparation of asymmetrized tris(hydroxymethyl)methane (THYM*) and of asymmetrized bis(hydroxymethyl)acetaldehyde (BHYMA*) as new highly versatile chiral building blocks

  摘要：

  A series of asymmetrized tris(hydroxymethyl)methanes 2 and bis(hydroxymethyl)acetaldehydes 3 have been prepared in both enantiomeric forms through a chemoenzymatic methodology. The key step is the highly enantioselective PPL-catalyzed monohydrolysis of 2(E)-alkenyl-1,3-diacetoxypropanes 25-27. A careful study on the effect of unsaturations adjacent to the prochiral center in a series of 2-substituted 1,3-diacetoxypropanes has confirmed the suggested beneficial effect of a pi-system in that position but has also unveiled an unprecedented dramatic effect of double-bond configuration on enantioselectivity. A new empirical model for the interpretation of these and other results, based both on polarity and steric arguments, is proposed. This study provides a general protocol for the efficient synthesis of asymmetrized 1,3-propanediols bearing in position 2 saturated or unsaturated carbon chains.

  DOI：

  10.1021/jo00031a039