1,17-Bis(tetrahydro-2H-pyran-2-yloxy)-5,8-heptadecadiyne | 162008-70-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 1,17-Bis(tetrahydro-2H-pyran-2-yloxy)-5,8-heptadecadiyne
• CAS: 162008-70-0
• 化学式: C₂₇H₄₄O₄
• 分子量: 432.644
• InChiKey: XNIZZPRRVHCINJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.37
• 重原子数：
  31.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1,17-Bis(tetrahydro-2H-pyran-2-yloxy)-5,8-heptadecadiyne 在 sodium tetrahydroborate 、 氢气 、 nickel diacetate 、 对甲苯磺酸 、 乙二胺 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 4.0h， 生成 5(Z),8(Z)-Heptadecadien-1,17-diol
  参考文献：
  名称：

  A Chemoenzymic Approach to Hydroperoxyeicosatetraenoic Acids. Total Synthesis of 5(S)-HPETE

  摘要：

  A new synthetic approach to enantiomerically pure hydroperoxyeicosatetraenoic acids (HPETEs) is described in which the tetraene skeleton is assembled through chemoselective olefination of a protected hydroperoxy aldehyde. Soybean lipoxygenase-mediated dioxygenation of both natural and unnatural fats produces hydroperoxy dienes in high enantiomeric excess; the observed regioselectivity supports a revised hypothesis for substrate specificity. Protection of the diene hydroperoxides as peroxy ketals is followed by regioselective ozonolysis to afford enantiomerically pure 4-peroxy 2,3-enals which undergo olefination to produce peroxytetraenoates. Removal of the monoperoxy ketal and the methyl ester affords enantiomerically pure HPETEs. The generality of the strategy is illustrated with the first chemical synthesis of 5(S)-HPETE.

  DOI：

  10.1021/jo00106a037
• 作为产物：
  描述：

  7-(tetrahydro-2H-pyran-2-yloxy)hept-2-yn-1-ol 在 咪唑 、 copper(I) bromide dimethylsulfide complex 、 乙基溴化镁 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 1,17-Bis(tetrahydro-2H-pyran-2-yloxy)-5,8-heptadecadiyne
  参考文献：
  名称：

  A Chemoenzymic Approach to Hydroperoxyeicosatetraenoic Acids. Total Synthesis of 5(S)-HPETE

  摘要：

  A new synthetic approach to enantiomerically pure hydroperoxyeicosatetraenoic acids (HPETEs) is described in which the tetraene skeleton is assembled through chemoselective olefination of a protected hydroperoxy aldehyde. Soybean lipoxygenase-mediated dioxygenation of both natural and unnatural fats produces hydroperoxy dienes in high enantiomeric excess; the observed regioselectivity supports a revised hypothesis for substrate specificity. Protection of the diene hydroperoxides as peroxy ketals is followed by regioselective ozonolysis to afford enantiomerically pure 4-peroxy 2,3-enals which undergo olefination to produce peroxytetraenoates. Removal of the monoperoxy ketal and the methyl ester affords enantiomerically pure HPETEs. The generality of the strategy is illustrated with the first chemical synthesis of 5(S)-HPETE.

  DOI：

  10.1021/jo00106a037