(2Z,4R,5R,6R,7S)-5,7-dihydroxy-4,6-dimethylnon-2-en-3-yl 2-methylpropanoate | 1262966-85-7

• 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: (2Z,4R,5R,6R,7S)-5,7-dihydroxy-4,6-dimethylnon-2-en-3-yl 2-methylpropanoate
• 英文别名: [(Z,4R,5R,6R,7S)-5,7-dihydroxy-4,6-dimethylnon-2-en-3-yl] 2-methylpropanoate
• CAS: 1262966-85-7
• 化学式: C₁₅H₂₈O₄
• 分子量: 272.385
• InChiKey: AMGGFPXDOIJULE-DKOQQAHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2Z,4R,5R,6R,7S)-5,7-dihydroxy-4,6-dimethylnon-2-en-3-yl 2-methylpropanoate 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到(3R,4R,5S,6S)-6-ethyl-4-hydroxy-3,5-dimethyltetrahydro-2H-pyran-2-one
  参考文献：
  名称：

  Total Asymmetric Syntheses of β-Hydroxy-δ-lactones via Umpolung with Sulfur Dioxide

  摘要：

  Cyclic stereotriads and stereotetrads of the beta-hydroxy-delta-lactone type, e.g. prelactones B and E, common in polyketides and polypropionates, are prepared via SO2-induced oxyallylations of enoxysilanes with (1E,3Z)-1-(1-phenylethoxy)penta-1,3-dien-3-yl carboxylates. Using (Z)- or (E)-enoxysilanes both 4,5-cis- or 4,5-trans-delta-lactones are obtained. Depending on the reduction method applied to the obtained aldol intermediates 5,6-trans or 5,6-cis-derivatives are formed. The delta-lactones can be prepared in both their enantiomeric forms depending on the (1R)- or (1S)-configuration of the starting 1-(1-phenylethoxy)penta-1,3-dienes.

  DOI：

  10.1021/jo102035d
• 作为产物：
  描述：

  三甲基(戊-2-烯-3-氧基)硅烷 在 二氧化硫 、 四氯化钛 、 双三氟甲烷磺酰亚胺 、 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 、 烯丙基三甲基硅烷 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 1.0h， 生成 (2Z,4R,5R,6R,7S)-5,7-dihydroxy-4,6-dimethylnon-2-en-3-yl 2-methylpropanoate
  参考文献：
  名称：

  Total Asymmetric Syntheses of β-Hydroxy-δ-lactones via Umpolung with Sulfur Dioxide

  摘要：

  Cyclic stereotriads and stereotetrads of the beta-hydroxy-delta-lactone type, e.g. prelactones B and E, common in polyketides and polypropionates, are prepared via SO2-induced oxyallylations of enoxysilanes with (1E,3Z)-1-(1-phenylethoxy)penta-1,3-dien-3-yl carboxylates. Using (Z)- or (E)-enoxysilanes both 4,5-cis- or 4,5-trans-delta-lactones are obtained. Depending on the reduction method applied to the obtained aldol intermediates 5,6-trans or 5,6-cis-derivatives are formed. The delta-lactones can be prepared in both their enantiomeric forms depending on the (1R)- or (1S)-configuration of the starting 1-(1-phenylethoxy)penta-1,3-dienes.

  DOI：

  10.1021/jo102035d

文献信息

• Total Asymmetric Syntheses of β-Hydroxy-δ-lactones via Umpolung with Sulfur Dioxide
  作者：Claudia J. Exner、Sylvain Laclef、Florent Poli、Maris Turks、Pierre Vogel

  DOI：10.1021/jo102035d

  日期：2011.2.4

  Cyclic stereotriads and stereotetrads of the beta-hydroxy-delta-lactone type, e.g. prelactones B and E, common in polyketides and polypropionates, are prepared via SO2-induced oxyallylations of enoxysilanes with (1E,3Z)-1-(1-phenylethoxy)penta-1,3-dien-3-yl carboxylates. Using (Z)- or (E)-enoxysilanes both 4,5-cis- or 4,5-trans-delta-lactones are obtained. Depending on the reduction method applied to the obtained aldol intermediates 5,6-trans or 5,6-cis-derivatives are formed. The delta-lactones can be prepared in both their enantiomeric forms depending on the (1R)- or (1S)-configuration of the starting 1-(1-phenylethoxy)penta-1,3-dienes.