(Z)-7-[(2R,3R)-3-((2Z,5Z)-(R)-1-Hydroxy-undeca-2,5-dienyl)-oxiranyl]-hept-5-enoic acid methyl ester | 213545-36-9

• 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: (Z)-7-[(2R,3R)-3-((2Z,5Z)-(R)-1-Hydroxy-undeca-2,5-dienyl)-oxiranyl]-hept-5-enoic acid methyl ester
• CAS: 213545-36-9
• 化学式: C₂₁H₃₄O₄
• 分子量: 350.499
• InChiKey: LNOUOVGMWIPMTL-XLJWJJENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.49
• 重原子数：
  25.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  59.06
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-(-)-α-甲氧基苯乙酸 、 (Z)-7-[(2R,3R)-3-((2Z,5Z)-(R)-1-Hydroxy-undeca-2,5-dienyl)-oxiranyl]-hept-5-enoic acid methyl ester 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (Z)-7-{(2R,3S)-3-[(2Z,5Z)-(R)-1-((R)-2-Methoxy-2-phenyl-acetoxy)-undeca-2,5-dienyl]-oxiranyl}-hept-5-enoic 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：

  rac-1-benzoyloxy-4-(tetrahydropyranyloxy)tetradec-2(E)-ene-5,8-diyne 在 2,4,6-三甲基吡啶 、 titanium(IV) isopropylate 、 甲醇 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 potassium carbonate 、 D-(-)-酒石酸二异丙酯 、 对甲苯磺酰氯 作用下， 以 异辛烷 、 二氯甲烷 、 氯仿 为溶剂， 反应 35.5h， 生成 (Z)-7-[(2R,3R)-3-((2Z,5Z)-(R)-1-Hydroxy-undeca-2,5-dienyl)-oxiranyl]-hept-5-enoic 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