(R)-2-(6-benzyloxy-4-methyl-4-hexenyl)propane-1,3-diol monoacetate | 588691-57-0

• 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: (R)-2-(6-benzyloxy-4-methyl-4-hexenyl)propane-1,3-diol monoacetate
• 英文别名: [(E,2R)-2-(hydroxymethyl)-6-methyl-8-phenylmethoxyoct-6-enyl] acetate
• CAS: 588691-57-0
• 化学式: C₁₉H₂₈O₄
• 分子量: 320.429
• InChiKey: OUCUWYXGQGTWJY-KZIRBZLESA-N

物化性质

• 沸点：
  444.4±45.0 °C(Predicted)
• 密度：
  1.050±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-(6-benzyloxy-4-methyl-4-hexenyl)propane-1,3-diol monoacetate 在 吡啶 、 lithium aluminium tetrahydride 、 氨 、 sodium 作用下， 生成 (E)-3,7-dimethyl-2-octene-1,8-diol
  参考文献：
  名称：

  Chemoenzymatic synthesis of (E)-3,7-dimethyl-2-octene-1,8-diol isolated from the hairpencils of male danaus chrysippus (African monarch)

  摘要：

  The synthesis of (E)-3,7-dimethyl-2-octene-1,8-diol (1), which was isolated from the hairpencils of male Danaus chrysippus (African Monarch), was investigated. The key step of the sequence involves asymmetric desymmetrization of the 1,3-propanediol 7 with lipase, in which high enantio selectivity was observed. Total synthesis afforded (S)-1 in 12 steps and 26% overall yield from readily available geraniol. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00352-4
• 作为产物：
  描述：

  乙酸乙烯酯 、 2-(6-benzyloxy-4-methyl-4-hexenyl)propane-1,3-diol 在 Pseudomonas cepacia lipase 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 23.0h， 以20%的产率得到2-(6-benzyloxy-4-methyl-4-hexenyl)propane-1,3-diol diacetate
  参考文献：
  名称：

  Chemoenzymatic synthesis of (E)-3,7-dimethyl-2-octene-1,8-diol isolated from the hairpencils of male danaus chrysippus (African monarch)

  摘要：

  The synthesis of (E)-3,7-dimethyl-2-octene-1,8-diol (1), which was isolated from the hairpencils of male Danaus chrysippus (African Monarch), was investigated. The key step of the sequence involves asymmetric desymmetrization of the 1,3-propanediol 7 with lipase, in which high enantio selectivity was observed. Total synthesis afforded (S)-1 in 12 steps and 26% overall yield from readily available geraniol. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00352-4