5-hydroxy-(5R)-3,6-dodecadiynyl 5-hydroxypentanoate | 443285-48-1

• 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: 5-hydroxy-(5R)-3,6-dodecadiynyl 5-hydroxypentanoate
• CAS: 443285-48-1
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: XVLFGMFVAVBFRR-MRXNPFEDSA-N

物化性质

• 沸点：
  453.6±45.0 °C(Predicted)
• 密度：
  1.071±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.03
• 重原子数：
  21.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-hydroxy-(5R)-3,6-dodecadiynyl 5-hydroxypentanoate 在 Lindlar's catalyst 喹啉 、 氢气 作用下， 以 乙醇 为溶剂， 以96%的产率得到5-hydroxy-(3Z,5R,6Z)-3,6-dodecadienyl 5-hydroxypentanoate
  参考文献：
  名称：

  Novel chiral lipoxygenase substrates: design and synthesis. Part 2

  摘要：

  A series of novel lipoxygenase substrates carrying a spacing modifier with a non-ionic hydroxyl terminus have been synthesized in an enantioselective fashion. One of the methylene hydrogens (flanked by the cis,cis-pentadienyl moiety) is replaced by alkyl, aryl and hydroxyl groups. The key steps in the synthesis involved enzymatic transesterification of 1,3-propanediol derivatives and two consecutive cis-selective Wittig olefinations. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00009-5
• 作为产物：
  描述：

  5-(4-methoxybenzyloxy)-(5R)-3,6-dodecadiynyl 5-(4-methoxybenzyloxy)pentanoate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以80%的产率得到5-hydroxy-(5R)-3,6-dodecadiynyl 5-hydroxypentanoate
  参考文献：
  名称：

  Novel chiral lipoxygenase substrates: design and synthesis. Part 2

  摘要：

  A series of novel lipoxygenase substrates carrying a spacing modifier with a non-ionic hydroxyl terminus have been synthesized in an enantioselective fashion. One of the methylene hydrogens (flanked by the cis,cis-pentadienyl moiety) is replaced by alkyl, aryl and hydroxyl groups. The key steps in the synthesis involved enzymatic transesterification of 1,3-propanediol derivatives and two consecutive cis-selective Wittig olefinations. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00009-5