methyl (5Z,8R)-8,9-dihydroxynon-5-enoate | 1072455-36-7

• 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)-8,9-dihydroxynon-5-enoate
• 英文别名: methyl (Z,8R)-8,9-dihydroxynon-5-enoate
• CAS: 1072455-36-7
• 化学式: C₁₀H₁₈O₄
• 分子量: 202.251
• InChiKey: XMLDAGVZSOKZFG-FIFYQCSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (5Z,8R)-8,9-dihydroxynon-5-enoate 在 咪唑 、 4-二甲氨基吡啶 、 草酰氯 、 lithium hydroxide monohydrate 、 cerium(III) chloride heptahydrate 、 2,4,6-三氯苯甲酰氯 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 氟化氢吡啶 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium bromide 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 aq. phosphate buffer 、 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.08h， 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：

  在 盐酸 、 水 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 为溶剂， 反应 18.0h， 生成 methyl (5Z,8R)-8,9-dihydroxynon-5-enoate
  参考文献：
  名称：

  Synthesis of marine oxylipin topsentolide A1 and its stereoisomers, and determination of the absolute configuration of the natural product

  摘要：

  Four possible stereoisomers of topsentolide A(1), a cytotoxic oxylipin against human solid tumor cell lines, were efficiently synthesized in a stereoselective manner in order to determine the stereochemistry of natural product. The absolute configuration of topsentolide A(1) was determined to be 8R,11R,12S by comparing NMR spectra and specific rotations of the synthetic isomers and the natural product. Cytotoxicity of the synthetic isomers was also examined. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.09.013

文献信息

• Enantioselective synthesis of methyl (5Z,8S)-8,9-epoxynon-5-enoate, an eicosanoid synthon
  作者：M. A. Lapitskaya、L. L. Vasiljeva、K. K. Pivnitsky

  DOI：10.1007/s11172-007-0257-z

  日期：2007.8

  A six-step synthesis of methyl (5Z,8S)-8,9-epoxynon-5-enoate, a known synthon of constanolactones and hepoxilins, from 5-hexynoic ester was developed. The enantiomeric purity of the synthon was attained by S-enantiodirected dihydroxylation of a double bond in the intermediate methyl non-8-en-5-ynoate with subsequent enantioselective hydrolysis of the epoxide group in the admixture of the minor R-enantiomer.

  本研究开发了一种从 5-己炔酸酯经六步合成 (5Z,8S)-8,9-环氧乙烷-5-烯酸甲酯的方法，这是一种已知的正己内酯和环紫杉素的合成物。通过对中间体非 8-en-5-ynoate 甲酯中的双键进行 S-enantiodirected dihydroxylation（S-对映体定向二羟基化），然后在混有次要 R-enantiomer 的情况下对环氧基团进行对映体选择性水解，从而获得对映体纯度较高的合成物。