methyl rac-13-hydroxy-10-(tetrahydropyranyloxy)tridec-11(E)-en-5,8-diynoate | 213545-16-5

• 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-13-hydroxy-10-(tetrahydropyranyloxy)tridec-11(E)-en-5,8-diynoate
• CAS: 213545-16-5
• 化学式: C₁₉H₂₆O₅
• 分子量: 334.412
• InChiKey: PZKNCWRDWPXSKV-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl rac-13-hydroxy-10-(tetrahydropyranyloxy)tridec-11(E)-en-5,8-diynoate 在 Lindlar's catalyst 、 palladium-lead 2,4,6-三甲基吡啶 、 喹啉 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 L-(+)-酒石酸二乙酯 、 氢气 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 、 氯仿 、 苯 为溶剂， 反应 34.5h， 生成 (5Z,8Z)-10-Hydroxy-10-[(2S,3S)-((Z)-3-oct-2-enyl)-oxiranyl]-deca-5,8-dienoic acid methyl ester
  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 甲醇 、 potassium carbonate 作用下， 反应 1.0h， 以3.15 g的产率得到methyl rac-13-hydroxy-10-(tetrahydropyranyloxy)tridec-11(E)-en-5,8-diynoate
  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