(-)-(4S,5S,6S,7S)-5,7-isopropylidenedioxy-4,6,8-trimethylnon-3-one | 1262966-91-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(4S,5S,6S,7S)-5,7-isopropylidenedioxy-4,6,8-trimethylnon-3-one
• 英文别名: (2S)-2-[(4S,5S,6S)-2,2,5-trimethyl-6-propan-2-yl-1,3-dioxan-4-yl]pentan-3-one
• CAS: 1262966-91-5
• 化学式: C₁₅H₂₈O₃
• 分子量: 256.386
• InChiKey: POBOLZIKUJXJSO-UVLXDEKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E)-2-methyl-3-trimethylsilyloxypent-3-ene 在 iron(III) chloride 、 methyllithium lithium bromide 、 二氧化硫 、 三正丁基氢锡 、 二甲基氯化铝 、 对甲苯磺酸 、 双三氟甲烷磺酰亚胺 、 烯丙基三甲基硅烷 作用下， 以 乙二醇二甲醚 、 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 6.17h， 生成 (-)-(4S,5S,6S,7S)-5,7-isopropylidenedioxy-4,6,8-trimethylnon-3-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

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.