methyl (5Z,8R,9E,11S,12S,14Z)-11-(1-ethoxyethoxy)-8-hydroxy-12-((4-methoxybenzyl)oxy)icosa-5,9,14-trienoate | 1610421-87-8

• 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: methyl (5Z,8R,9E,11S,12S,14Z)-11-(1-ethoxyethoxy)-8-hydroxy-12-((4-methoxybenzyl)oxy)icosa-5,9,14-trienoate
• CAS: 1610421-87-8
• 化学式: C₃₃H₅₂O₇
• 分子量: 560.772
• InChiKey: XOJRJOZQNGAVKG-QRWVTOMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.08
• 重原子数：
  40.0
• 可旋转键数：
  23.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  methyl (5Z,8R,9E,11S,12S,14Z)-11-(1-ethoxyethoxy)-8-hydroxy-12-((4-methoxybenzyl)oxy)icosa-5,9,14-trienoate 在 4-二甲氨基吡啶 、 lithium hydroxide monohydrate 、 2,4,6-三氯苯甲酰氯 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 aq. phosphate buffer 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 17.0h， 生成 (6Z,9R)-9-[(1E,3R,4S,6Z)-3,4-epoxy-1,6-dodecadienyl]-4,5,8,9-tetrahydro-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：

  methyl (5Z,8R)-8,9-bis[(tert-butyldimethylsilyl)oxy]-5-nonenoate 在 草酰氯 、 cerium(III) chloride heptahydrate 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 氟化氢吡啶 、 二甲基亚砜 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 为溶剂， 反应 31.08h， 生成 methyl (5Z,8R,9E,11S,12S,14Z)-11-(1-ethoxyethoxy)-8-hydroxy-12-((4-methoxybenzyl)oxy)icosa-5,9,14-trienoate
  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