Acetic acid (R)-2-hydroxymethyl-nonyl ester | 133490-89-8

• 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: Acetic acid (R)-2-hydroxymethyl-nonyl ester
• CAS: 133490-89-8
• 化学式: C₁₂H₂₄O₃
• 分子量: 216.321
• InChiKey: QGGZVZUTKAIESE-GFCCVEGCSA-N

物化性质

• 沸点：
  268.3±13.0 °C(Predicted)
• 密度：
  0.948±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  15.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  庚醛 在 palladium on activated charcoal 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氢气 、 哌啶乙酸盐 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 异丙醇 、 苯 为溶剂， 反应 25.67h， 生成 Acetic acid (R)-2-hydroxymethyl-nonyl ester
  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

文献信息

• Enzymatic asymmetrization of some prochiral and meso diols through monoacetylation with pig pancreatic lipase (PPL)
  作者：Giuseppe Guanti、Luca Banfi、Renata Riva

  DOI：10.1016/s0957-4166(00)80471-1

  日期：1994.1

  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.
• Enzymes in organic synthesis: remarkable influence of a π system on the enantioselectivity in PPL catalysed monohydrolysis of 2-substituted 1,3-diacetoxypropanes.
  作者：Giuseppe Guanti、Luca Banfi、Enrica Narisano

  DOI：10.1016/s0957-4166(00)82383-6

  日期：1990.1