methyl rac-13-benzoyloxy-10-hydroxytridec-11(E)-ene-5,8-diynoate | 213545-12-1

• 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: methyl rac-13-benzoyloxy-10-hydroxytridec-11(E)-ene-5,8-diynoate
• CAS: 213545-12-1
• 化学式: C₂₁H₂₂O₅
• 分子量: 354.403
• InChiKey: YFVZMZOCRFGXDG-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.83
• 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-benzoyloxy-10-hydroxytridec-11(E)-ene-5,8-diynoate 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 、 L-(+)-酒石酸二乙酯 、 4-甲基苯磺酸吡啶 、 potassium carbonate 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 38.5h， 生成 10(R/S)-hydroxy-11(R),12(S)-epoxy-5,8,14-eicosatriynoate
  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 methyl rac-13-benzoyloxy-10-hydroxytridec-11(E)-ene-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

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.