2-(8-hydroxyoctyl)-2H,3H,6H-oxin-6-ol | 302969-88-6

• 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-(8-hydroxyoctyl)-2H,3H,6H-oxin-6-ol
• 英文别名: 2-(8-hydroxyoctyl)-3,6-dihydro-2H-pyran-6-ol
• CAS: 302969-88-6
• 化学式: C₁₃H₂₄O₃
• 分子量: 228.332
• InChiKey: RRYYGMRBYHKCAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  2-(8-hydroxyoctyl)-2H,3H,6H-oxin-6-ol 在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以73%的产率得到8-(3-oxo-1H,6H-2-oxinyl)octanoic 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
• 作为产物：
  描述：

  1-(α-ethoxyethoxy)dec-9-ene 在 Lindlar's catalyst 2,6-二甲基吡啶 、 喹啉 、 sodium periodate 、 正丁基锂 、 氢气 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 67.51h， 生成 2-(8-hydroxyoctyl)-2H,3H,6H-oxin-6-ol
  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.