2-(6-benzyloxy-4-methyl-4-hexenyl)propane-1,3-diol | 588691-55-8

• 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: 2-(6-benzyloxy-4-methyl-4-hexenyl)propane-1,3-diol
• 英文别名: 2-[(E)-4-methyl-6-phenylmethoxyhex-4-enyl]propane-1,3-diol
• CAS: 588691-55-8
• 化学式: C₁₇H₂₆O₃
• 分子量: 278.392
• InChiKey: VJRCRUMYNOICQL-XNTDXEJSSA-N

物化性质

• 沸点：
  431.2±45.0 °C(Predicted)
• 密度：
  1.046±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  (E)-4-methyl-6-(phenylmethoxy)-4-hexenal 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 sodium hydride 作用下， 生成 2-(6-benzyloxy-4-methyl-4-hexenyl)propane-1,3-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

文献信息

• Chemoenzymatic synthesis of (E)-3,7-dimethyl-2-octene-1,8-diol isolated from the hairpencils of male danaus chrysippus (African monarch)
  作者：Kunihiko Takabe、Nobuyuki Mase、Hiroya Hashimoto、Atsushi Tsuchiya、Takashi Ohbayashi、Hidemi Yoda

  DOI：10.1016/s0960-894x(03)00352-4

  日期：2003.6

  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.