rac-1-(benzoyloxy)tetradec-2(E)-ene-5,8-diyn-4-ol | 213545-21-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: rac-1-(benzoyloxy)tetradec-2(E)-ene-5,8-diyn-4-ol
• 英文别名: [(E)-4-hydroxytetradec-2-en-5,8-diynyl] benzoate
• CAS: 213545-21-2
• 化学式: C₂₁H₂₄O₃
• 分子量: 324.42
• InChiKey: HWPUPGAYERABIL-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  rac-1-(benzoyloxy)tetradec-2(E)-ene-5,8-diyn-4-ol 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 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 D-(-)-酒石酸二异丙酯 、 对甲苯磺酰氯 、 N,N'-二环己基碳二亚胺 作用下， 以 异辛烷 、 二氯甲烷 、 氯仿 为溶剂， 反应 56.5h， 生成 (Z)-7-{(2S,3R)-3-[(2Z,5Z)-(S)-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：

  4‐hydroxybut‐2‐en‐1‐yl benzoate 在 copper(l) iodide 、 重铬酸吡啶 、 正丁基锂 、 MS 3 Angstroem 、 potassium carbonate 、 溶剂黄146 、 sodium iodide 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.17h， 生成 rac-1-(benzoyloxy)tetradec-2(E)-ene-5,8-diyn-4-ol
  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

• 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.