(3S,4S,5E)-3,4-dimethyl-5-octen-1-ol | 136185-49-4

• 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: (3S,4S,5E)-3,4-dimethyl-5-octen-1-ol
• CAS: 136185-49-4
• 化学式: C₁₀H₂₀O
• 分子量: 156.268
• InChiKey: IJNWCLUMJKGVMI-ROSGPLSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.61
• 重原子数：
  11.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (3S,4S,5E)-3,4-dimethyl-5-octen-1-ol 在 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 (2S,3S)-2,3-dimethyl-5-(tetrahydropyran-2-yloxy)-1-pentanol
  参考文献：
  名称：

  通过阴离子氧基-Cope重排进行非环状非对映控制和不对称传递。（+）-呋喃醛和（-）-鸟氨酸的关键前体的合成

  摘要：

  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).

  DOI：

  10.1016/s0040-4020(01)86283-9
• 作为产物：
  描述：

  (3S,4S,5E)-3,4-dimethyl-5-octenal 在 二异丁基氢化铝 作用下， 以93%的产率得到(3S,4S,5E)-3,4-dimethyl-5-octen-1-ol
  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: 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.
• 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).