methyl rac-10-hydroxyeicos-11(E)-ene-5,8,14-triynoate | 213545-27-8

• 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 rac-10-hydroxyeicos-11(E)-ene-5,8,14-triynoate
• 英文别名: methyl (E)-10-hydroxyicos-11-en-5,8,14-triynoate
• CAS: 213545-27-8
• 化学式: C₂₁H₂₈O₃
• 分子量: 328.452
• InChiKey: PRSMNWHNIVQQQA-SAPNQHFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl rac-10-hydroxyeicos-11(E)-ene-5,8,14-triynoate 在 氧气 作用下， 以 苯 为溶剂， 反应 2922.0h， 以40%的产率得到methyl 10-oxoeicos-11(E)-en-5,8,14-triynoate
  参考文献：
  名称：

  Synthetic research on hepoxilins

  摘要：

  A new synthetic strategy for hydroxy-epoxy eicosanoids formed through the lipoxygenase pathway is developed. It makes use of a single synthon of the central functionalized fragment of the target molecules, namely racemic (E)-ClCH2C=CCHOHCH=CHCH(2)OBz. Elongation of the carbon chain of the synthon by successive condensations at both ends alternatively with hept-1-yne and hex-5-ynoic acid followed by enantioselective double bond epoxidation and partial hydrogenation of the triple bonds resulted in the syntheses of hepoxilins B-3, their potential 8-lipoxygenase analogs, or their enantiomers, depending on the sequence of carbon chain elongations and the chirality of the epoxidation controller used.

  DOI：

  10.1007/bf02503497
• 作为产物：
  描述：

  methyl rac-13-benzoyloxy-10-(tetrahydropyranyloxy)tridec-11(E)-ene-5,8-diynoate 在 2,4,6-三甲基吡啶 、 甲醇 、 4-二甲氨基吡啶 、 potassium carbonate 、 对甲苯磺酰氯 作用下， 以 氯仿 为溶剂， 反应 33.5h， 生成 methyl rac-10-hydroxyeicos-11(E)-ene-5,8,14-triynoate
  参考文献：
  名称：

  Synthetic research on hepoxilins

  摘要：

  A new synthetic strategy for hydroxy-epoxy eicosanoids formed through the lipoxygenase pathway is developed. It makes use of a single synthon of the central functionalized fragment of the target molecules, namely racemic (E)-ClCH2C=CCHOHCH=CHCH(2)OBz. Elongation of the carbon chain of the synthon by successive condensations at both ends alternatively with hept-1-yne and hex-5-ynoic acid followed by enantioselective double bond epoxidation and partial hydrogenation of the triple bonds resulted in the syntheses of hepoxilins B-3, their potential 8-lipoxygenase analogs, or their enantiomers, depending on the sequence of carbon chain elongations and the chirality of the epoxidation controller used.

  DOI：

  10.1007/bf02503497

文献信息

• Enantiodivergent total synthesis of trioxilins B3 using Sharpless asymmetric olefin dihydroxylation
  作者：Margarita A. Lapitskaya、Ljudmila L. Vasiljeva、Peter M. Demin、Kasimir K. Pivnitsky

  DOI：10.1070/mc2004v014n06abeh002003

  日期：2004.1

  The unknown 11, 12-threo-stereoisomers of B-type trioxilins, (10R, 11R, 12S)-TrXB3, its (10S)-epimer and their enantiomers were synthesized (as methyl esters) from a common racemic precursor, viz., methyl rac-10-hydroxyeicos-11 (E)-ene-5,8,14-triynoate, by Sharpless enantiodirected dihydroxylation of the double bond as the key step.
• Synthetic research on hepoxilins
  作者：V. I. Mel'nikova、L. L. Vasil'eva、K. K. Pivnitsky

  DOI：10.1007/bf02503497

  日期：1998.6

  A new synthetic strategy for hydroxy-epoxy eicosanoids formed through the lipoxygenase pathway is developed. It makes use of a single synthon of the central functionalized fragment of the target molecules, namely racemic (E)-ClCH2C=CCHOHCH=CHCH(2)OBz. Elongation of the carbon chain of the synthon by successive condensations at both ends alternatively with hept-1-yne and hex-5-ynoic acid followed by enantioselective double bond epoxidation and partial hydrogenation of the triple bonds resulted in the syntheses of hepoxilins B-3, their potential 8-lipoxygenase analogs, or their enantiomers, depending on the sequence of carbon chain elongations and the chirality of the epoxidation controller used.