(1E,3S,4S,6Z,9Z)-4-((tert-butyldimethylsilyl)oxy)-1-((S,Z)-9-oxo-2,3,6,7,8,9-hexahydrooxonin-2-yl)dodeca-1,6,9-trien-3-yl methanesulfonate | 1228569-51-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (1E,3S,4S,6Z,9Z)-4-((tert-butyldimethylsilyl)oxy)-1-((S,Z)-9-oxo-2,3,6,7,8,9-hexahydrooxonin-2-yl)dodeca-1,6,9-trien-3-yl methanesulfonate
• CAS: 1228569-51-4
• 化学式: C₂₇H₄₆O₆SSi
• 分子量: 526.81
• InChiKey: IZPSTDIZMPBRMD-XBFFJMLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.62
• 重原子数：
  35.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1E,3S,4S,6Z,9Z)-4-((tert-butyldimethylsilyl)oxy)-1-((S,Z)-9-oxo-2,3,6,7,8,9-hexahydrooxonin-2-yl)dodeca-1,6,9-trien-3-yl methanesulfonate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 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：

  Determination of the absolute configuration of marine oxylipin topsentolide A1 by the synthesis of the enantiomer of the natural product

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2010.03.071
• 作为产物：
  描述：

  (2S,4Z,7Z)-2-(tert-butyldimethylsilyloxy)deca-4,7-dien-1-ol 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 N-碘代丁二酰亚胺 、 正丁基锂 、 草酰氯 、 cerium(III) chloride heptahydrate 、 potassium carbonate 、 二甲基亚砜 、 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 5.83h， 生成 (1E,3S,4S,6Z,9Z)-4-((tert-butyldimethylsilyl)oxy)-1-((S,Z)-9-oxo-2,3,6,7,8,9-hexahydrooxonin-2-yl)dodeca-1,6,9-trien-3-yl methanesulfonate
  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