(3S,4S,5E)-3,4-dimethyl-1-(tetrahydropyran-2-yloxy)-5-octene | 136185-50-7

• 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: (3S,4S,5E)-3,4-dimethyl-1-(tetrahydropyran-2-yloxy)-5-octene
• CAS: 136185-50-7
• 化学式: C₁₅H₂₈O₂
• 分子量: 240.386
• InChiKey: SPSWYOHLAVCVAF-FVGWNYLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.16
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3S,4S,5E)-3,4-dimethyl-1-(tetrahydropyran-2-yloxy)-5-octene 在 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 作用下， 生成 (2S,3S)-2,3-dimethyl-5-(tetrahydropyran-2-yloxy)-1-pentanol
  参考文献：
  名称：

  Acyclic diastereocontrol and asymmetric transmission via anionic oxy-Cope rearrangement: a synthetic application of sequential [2,3]Wittig-oxy-Cope rearrangements

  摘要：

  The anionic oxy-Cope rearrangements of acyclic 1,5-dien-3-ols with the 3,4-erythro configuration established by the [2,3]Wittig rearrangement are shown to provide a useful level of diastereoselection and asymmetric transmission in the context of a formal asymmetric synthesis of an insect pheromone.

  DOI：

  10.1021/jo00021a002
• 作为产物：
  描述：

  (3S,4S,5E)-3,4-dimethyl-5-octenal 在 氢气 、 二异丁基氢化铝 作用下， 生成 (3S,4S,5E)-3,4-dimethyl-1-(tetrahydropyran-2-yloxy)-5-octene
  参考文献：
  名称：

  Acyclic diastereocontrol and asymmetric transmission via anionic oxy-Cope rearrangement: a synthetic application of sequential [2,3]Wittig-oxy-Cope rearrangements

  摘要：

  The anionic oxy-Cope rearrangements of acyclic 1,5-dien-3-ols with the 3,4-erythro configuration established by the [2,3]Wittig rearrangement are shown to provide a useful level of diastereoselection and asymmetric transmission in the context of a formal asymmetric synthesis of an insect pheromone.

  DOI：

  10.1021/jo00021a002

文献信息

• Acyclic diastereocontrol and asymmetric transmission via anionic oxy-Cope rearrangement. Synthesis of key precursors of (+)-faranal and (−)-antirhine
  作者：Shih-Yi Wei、Katsuhiko Tomooka、Takeshi Nakai

  DOI：10.1016/s0040-4020(01)86283-9

  日期：1993.1

  The anionic oxy-Cope rearrangements of acyclic 1,5-dien-3-ols, when their stereochemistries are properly designated. are shown to proceed with a high level of diastereoselection and asymmetric transmission. The utility of the acyclic oxy-Cope variants is demonstrated by the stereocontrolled synthesis of the key precursors of (+)-faranal (insect pheromone) and (-)-antirhine (Corynanthe-type indole alkaloid).
• Acyclic diastereocontrol and asymmetric transmission via anionic oxy-Cope rearrangement: a synthetic application of sequential [2,3]Wittig-oxy-Cope rearrangements
  作者：Shih Yi Wei、Katsuhiko Tomooka、Takeshi Nakai

  DOI：10.1021/jo00021a002

  日期：1991.10

  The anionic oxy-Cope rearrangements of acyclic 1,5-dien-3-ols with the 3,4-erythro configuration established by the [2,3]Wittig rearrangement are shown to provide a useful level of diastereoselection and asymmetric transmission in the context of a formal asymmetric synthesis of an insect pheromone.