(1',2',5,6-2H4)-6-(4'-hydroxy-but-1'-enylsulfanyl)-hex-5-enoic acid tert-butyl ester | 947264-11-1

• 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: (1',2',5,6-2H4)-6-(4'-hydroxy-but-1'-enylsulfanyl)-hex-5-enoic acid tert-butyl ester
• CAS: 947264-11-1
• 化学式: C₁₄H₂₄O₃S
• 分子量: 276.377
• InChiKey: XOEPDXHGVCLBAB-JQAKUTQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  18.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1',2',5,6-2H4)-6-(4'-hydroxy-but-1'-enylsulfanyl)-hex-5-enoic acid tert-butyl ester 在 吡啶 、 溴 、 sodium hexamethyldisilazane 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 33.75h， 生成 tert-butyl 7-thia(5,6,8,9-2H4)arachidonate
  参考文献：
  名称：

  Synthesis of 7-thiaarachidonic acid as a mechanistic probe of prostaglandin H synthase-2

  摘要：

  The mechanism by which prostaglandin synthase converts arachidonic acid to prostaglandin G(2), creating five new chiral centers in the process, is still incompletely understood. The first radical intermediate has been characterized by EPR spectroscopy but subsequent proposed intermediates have not succumbed to detection. We report the synthesis of 7-thiaarachidonic acid designed to stabilize one of the proposed radical intermediates, which may allow its detection. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.073
• 作为产物：
  描述：

  5-己炔酸 在 1-己炔 吡啶 、 正丁基锂 、 四丁基氟化铵 、 锌 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 苯 为溶剂， 反应 23.42h， 生成 (1',2',5,6-2H4)-6-(4'-hydroxy-but-1'-enylsulfanyl)-hex-5-enoic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of 7-thiaarachidonic acid as a mechanistic probe of prostaglandin H synthase-2

  摘要：

  The mechanism by which prostaglandin synthase converts arachidonic acid to prostaglandin G(2), creating five new chiral centers in the process, is still incompletely understood. The first radical intermediate has been characterized by EPR spectroscopy but subsequent proposed intermediates have not succumbed to detection. We report the synthesis of 7-thiaarachidonic acid designed to stabilize one of the proposed radical intermediates, which may allow its detection. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.073