4-hydroxyundec-1-ene-1,11-dicarboxylic acid | 302969-86-4

• 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: 4-hydroxyundec-1-ene-1,11-dicarboxylic acid
• 英文别名: (2E)-5-hydroxytridec-2-enedioic acid；(E)-5-hydroxytridec-2-enedioic acid
• CAS: 302969-86-4
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: DZNDHQLHAMNVLI-UXBLZVDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  甲醇 、 4-hydroxyundec-1-ene-1,11-dicarboxylic acid 在 二氯乙基铝 作用下， 以 正己烷 为溶剂， 反应 2.5h， 以70%的产率得到methyl 8-(3-oxo-1H,6H-2-oxinyl)octanoate
  参考文献：
  名称：

  Total Synthesis of Oxidized Phospholipids. 3. The (11E)-9-Hydroxy-13-oxotridec-11-enoate Ester of 2-Lysophosphatidylcholine

  摘要：

  A total synthesis of (11E)-9-hydroxy-13-oxotridec-11-enoate ester of 2-lysophosphatidylcholine (HOT-PC) was devised to facilitate identification of this oxidized phospholipid. A lactone, 8-(3-oxo-1H,6H-2-oxinyl)octanoic acid (1), believed to be generated through an intermediate (11E)-9-hydroxy-13-oxotridec-11-enoic acid (HOT), is produced upon autoxidation of linoleic acid. A synthesis of lactone 1 methyl ester was accomplished from HOT involving a novel trans-cis isomerization that is driven to completion by cyclization to a hemiacetal. An alternative route to this carbon skeleton was also acheived that provides the lactone 1 itself.

  DOI：

  10.1021/jo000809u
• 作为产物：
  描述：

  (11E)-9-hydroxy-13-oxotridec-11-enoic acid 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 2.5h， 以95%的产率得到4-hydroxyundec-1-ene-1,11-dicarboxylic acid
  参考文献：
  名称：

  Total Synthesis of Oxidized Phospholipids. 3. The (11E)-9-Hydroxy-13-oxotridec-11-enoate Ester of 2-Lysophosphatidylcholine

  摘要：

  A total synthesis of (11E)-9-hydroxy-13-oxotridec-11-enoate ester of 2-lysophosphatidylcholine (HOT-PC) was devised to facilitate identification of this oxidized phospholipid. A lactone, 8-(3-oxo-1H,6H-2-oxinyl)octanoic acid (1), believed to be generated through an intermediate (11E)-9-hydroxy-13-oxotridec-11-enoic acid (HOT), is produced upon autoxidation of linoleic acid. A synthesis of lactone 1 methyl ester was accomplished from HOT involving a novel trans-cis isomerization that is driven to completion by cyclization to a hemiacetal. An alternative route to this carbon skeleton was also acheived that provides the lactone 1 itself.

  DOI：

  10.1021/jo000809u

文献信息

• Total Synthesis of Oxidized Phospholipids. 3. The (11<i>E</i>)-9-Hydroxy-13-oxotridec-11-enoate Ester of 2-Lysophosphatidylcholine
  作者：Yijun Deng、Robert G. Salomon

  DOI：10.1021/jo000809u

  日期：2000.10.1

  A total synthesis of (11E)-9-hydroxy-13-oxotridec-11-enoate ester of 2-lysophosphatidylcholine (HOT-PC) was devised to facilitate identification of this oxidized phospholipid. A lactone, 8-(3-oxo-1H,6H-2-oxinyl)octanoic acid (1), believed to be generated through an intermediate (11E)-9-hydroxy-13-oxotridec-11-enoic acid (HOT), is produced upon autoxidation of linoleic acid. A synthesis of lactone 1 methyl ester was accomplished from HOT involving a novel trans-cis isomerization that is driven to completion by cyclization to a hemiacetal. An alternative route to this carbon skeleton was also acheived that provides the lactone 1 itself.