(7E,11Z)-5-Acetyl-6-formyl-9-hydroxy-heptadeca-7,11-dienoic acid | 197239-64-8

• 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: (7E,11Z)-5-Acetyl-6-formyl-9-hydroxy-heptadeca-7,11-dienoic acid
• 英文别名: (7E,11Z)-5-acetyl-6-formyl-9-hydroxyheptadeca-7,11-dienoic acid
• CAS: 197239-64-8
• 化学式: C₂₀H₃₂O₅
• 分子量: 352.471
• InChiKey: GBEDJTHHSCZHJV-ISHIJUGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (7E,11Z)-5-Acetyl-6-formyl-9-hydroxy-heptadeca-7,11-dienoic acid 在 N,N-二异丙基乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 2.17h， 生成
  参考文献：
  名称：

  Total Synthesis of Iso[4]-levuglandin E₂

  摘要：

  Iso[4]-levuglandin E-2 (iso[4]-LGE(2), 5-acetyl-6-formyl-9-hydroxy-7(E),11(Z)-heptadecadienoic acid) is a structural isomer of levuglandin E-2 (8-acetyl-9-formyl-12-hydroxy-5(Z),10(E)-heptadecadienoic acid) that we postulate to be generated during autoxidation of arachidonic acid or arachidonate esters. To facilitate detection and identification of iso[4]-LGE(2) in biological samples, a succinct total synthesis was developed that depends on conjugate addition of a higher order vinyl cyanocuprate to a gamma-alkoxy enone to provide a key carbon-carbon bond-forming step. Bismethoxime pentafluorobenzyl ester trimethylsilyl ether derivatives of LGE(2) and iso[4]-LGE(2) were prepared and shown to be suitable for mass spectral identification of these highly oxidized lipids.

  DOI：

  10.1021/jo970858f
• 作为产物：
  描述：

  (7E,11Z)-(S)-5-Acetyl-6-((S)-1,2-dihydroxy-ethyl)-9-hydroxy-heptadeca-7,11-dienoic acid 在 sodium periodate 作用下， 以 水 、 丙酮 为溶剂， 反应 1.75h， 以93%的产率得到(7E,11Z)-5-Acetyl-6-formyl-9-hydroxy-heptadeca-7,11-dienoic acid
  参考文献：
  名称：

  Total Synthesis of Iso[4]-levuglandin E₂

  摘要：

  Iso[4]-levuglandin E-2 (iso[4]-LGE(2), 5-acetyl-6-formyl-9-hydroxy-7(E),11(Z)-heptadecadienoic acid) is a structural isomer of levuglandin E-2 (8-acetyl-9-formyl-12-hydroxy-5(Z),10(E)-heptadecadienoic acid) that we postulate to be generated during autoxidation of arachidonic acid or arachidonate esters. To facilitate detection and identification of iso[4]-LGE(2) in biological samples, a succinct total synthesis was developed that depends on conjugate addition of a higher order vinyl cyanocuprate to a gamma-alkoxy enone to provide a key carbon-carbon bond-forming step. Bismethoxime pentafluorobenzyl ester trimethylsilyl ether derivatives of LGE(2) and iso[4]-LGE(2) were prepared and shown to be suitable for mass spectral identification of these highly oxidized lipids.

  DOI：

  10.1021/jo970858f

文献信息

• Total Synthesis of Iso[4]-levuglandin E₂
  作者：Ganesamoorthy Subbanagounder、Robert G. Salomon、Krishna K. Murthi、Cynthia Brame、L. Jackson Roberts

  DOI：10.1021/jo970858f

  日期：1997.10.1

  Iso[4]-levuglandin E-2 (iso[4]-LGE(2), 5-acetyl-6-formyl-9-hydroxy-7(E),11(Z)-heptadecadienoic acid) is a structural isomer of levuglandin E-2 (8-acetyl-9-formyl-12-hydroxy-5(Z),10(E)-heptadecadienoic acid) that we postulate to be generated during autoxidation of arachidonic acid or arachidonate esters. To facilitate detection and identification of iso[4]-LGE(2) in biological samples, a succinct total synthesis was developed that depends on conjugate addition of a higher order vinyl cyanocuprate to a gamma-alkoxy enone to provide a key carbon-carbon bond-forming step. Bismethoxime pentafluorobenzyl ester trimethylsilyl ether derivatives of LGE(2) and iso[4]-LGE(2) were prepared and shown to be suitable for mass spectral identification of these highly oxidized lipids.