(5Z,8R,9E,11S,12S,14Z)-8-hydroxy-11-methoxy-12-(4-methoxyphenyl)methoxy-5,9,14-icosatrienoic acid | 1610421-85-6

• 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: (5Z,8R,9E,11S,12S,14Z)-8-hydroxy-11-methoxy-12-(4-methoxyphenyl)methoxy-5,9,14-icosatrienoic acid
• CAS: 1610421-85-6
• 化学式: C₂₉H₄₄O₆
• 分子量: 488.665
• InChiKey: HWKODAJACFZMGS-DPGGADDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.24
• 重原子数：
  35.0
• 可旋转键数：
  20.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  85.22
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (5Z,8R,9E,11S,12S,14Z)-8-hydroxy-11-methoxy-12-(4-methoxyphenyl)methoxy-5,9,14-icosatrienoic acid 在 2,4,6-三氯苯甲酰氯 、 N,N-二异丙基乙胺 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 11.0h， 以95%的产率得到(6Z,9R)-4,5,8,9-tetrahydro-9-[(1E,3S,4S,6Z)-3-methoxy-4-(4-methoxyphenyl)methoxy-1,6-dodecadienyl]-2(3H)-oxoninone
  参考文献：
  名称：

  Synthesis of topsentolides A2 and C2, and non-enzymatic conversion of the former to the latter

  摘要：

  The first total synthesis of the marine-derived cytotoxin topsentolide A(2), which eventually culminated in its stereochemical determination, was accomplished in 17 steps from a known chiral alcohol. An improved synthesis of its congener, topsentolide C-2, from a synthetic intermediate of topsentolide A(2) was also performed by utilizing the Yamaguchi lactonization to construct its nine-membered lactone ring. Treatment of epoxide ring-containing topsentolide Ay with HCl/MeOH brought about its quantitative conversion into topsentolide C-2. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.040
• 作为产物：
  描述：

  dimethyl [(3S,5Z)-3-(4-methoxyphenyl)methoxy-2-oxo-5-undecenyl]phosphonate 在 六甲基磷酰三胺 、 lithium hydroxide monohydrate 、 cerium(III) chloride heptahydrate 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 23.08h， 生成 (5Z,8R,9E,11S,12S,14Z)-8-hydroxy-11-methoxy-12-(4-methoxyphenyl)methoxy-5,9,14-icosatrienoic acid
  参考文献：
  名称：

  Synthesis of topsentolides A2 and C2, and non-enzymatic conversion of the former to the latter

  摘要：

  The first total synthesis of the marine-derived cytotoxin topsentolide A(2), which eventually culminated in its stereochemical determination, was accomplished in 17 steps from a known chiral alcohol. An improved synthesis of its congener, topsentolide C-2, from a synthetic intermediate of topsentolide A(2) was also performed by utilizing the Yamaguchi lactonization to construct its nine-membered lactone ring. Treatment of epoxide ring-containing topsentolide Ay with HCl/MeOH brought about its quantitative conversion into topsentolide C-2. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.040