5-(4-methoxybenzyloxy)-(5R)-3,6-dodecadiyn-1-ol | 443285-46-9

• 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-(4-methoxybenzyloxy)-(5R)-3,6-dodecadiyn-1-ol
• 英文别名: (5R)-5-[(4-Methoxyphenyl)methoxy]-3,6-dodecadiyn-1-ol；(5R)-5-[(4-methoxyphenyl)methoxy]dodeca-3,6-diyn-1-ol
• CAS: 443285-46-9
• 化学式: C₂₀H₂₆O₃
• 分子量: 314.425
• InChiKey: KHWBTMDMDQETRZ-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(4-methoxybenzyloxy)-(5R)-3,6-dodecadiyn-1-ol 在 Lindlar's catalyst 喹啉 、 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 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：

  2,2,2-三氯代亚氨逐乙酸-4-甲氧基苄酯 在 camphor-10-sulfonic acid 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 2.0h， 生成 5-(4-methoxybenzyloxy)-(5R)-3,6-dodecadiyn-1-ol
  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

文献信息

• Novel chiral lipoxygenase substrates: design and synthesis. Part 2
  作者：J.S. Yadav、S. Nanda

  DOI：10.1016/s0957-4166(02)00009-5

  日期：2001.12

  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.