(5Z,8S,9E,11R,12S,14Z,17Z)-11,12-epoxyicosa-5,9,14,17-tetraen-8-olide | 1229964-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (5Z,8S,9E,11R,12S,14Z,17Z)-11,12-epoxyicosa-5,9,14,17-tetraen-8-olide
• 英文别名: Topsentolide A2；(2S,4Z)-2-[(E)-2-[(2R,3S)-3-[(2Z,5Z)-octa-2,5-dienyl]oxiran-2-yl]ethenyl]-3,6,7,8-tetrahydro-2H-oxonin-9-one
• CAS: 1229964-81-1
• 化学式: C₂₀H₂₈O₃
• 分子量: 316.441
• InChiKey: VZWNYWSEUACDLE-VYXNFCKLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl (2S,4Z,7Z)-2-(tert-butyldimethylsilyloxy)deca-4,7-dienoate 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 正丁基锂 、 cerium(III) chloride heptahydrate 、 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 乙腈 为溶剂， 反应 4.67h， 生成 (5Z,8S,9E,11R,12S,14Z,17Z)-11,12-epoxyicosa-5,9,14,17-tetraen-8-olide
  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

• Determination of the absolute configuration of marine oxylipin topsentolide A1 by the synthesis of the enantiomer of the natural product
  作者：Munetaka Kobayashi、Ken Ishigami、Hidenori Watanabe

  DOI：10.1016/j.tetlet.2010.03.071

  日期：2010.5

  Two possible stereoisomers of topsentolide A(1), a cytotoxic oxylipin against human solid tumor cell lines, were prepared in order to determine the stereochemistry of natural product. That is, the enantiomer of topsentolide A(1), (85,115,12R)-isomer, and its diastereomer was efficiently synthesized in a stereoselective manner. The stereochemistry 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. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of marine oxylipin topsentolide A1 and its stereoisomers, and determination of the absolute configuration of the natural product
  作者：Ken Ishigami、Munetaka Kobayashi、Motoki Takagi、Kazuo Shin-ya、Hidenori Watanabe

  DOI：10.1016/j.tet.2015.09.013

  日期：2015.11

  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.