(1α,2β,3aα,6aα)-Octahydro-1,5,5-trimethylpentalene-1,2-diol | 131833-53-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1α,2β,3aα,6aα)-Octahydro-1,5,5-trimethylpentalene-1,2-diol
• 英文别名: (1S,2S,3aR,6aR)-1,5,5-trimethyl-2,3,3a,4,6,6a-hexahydropentalene-1,2-diol
• CAS: 131833-53-9
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: JFRRJVAZQGQGBR-DKIAZLNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1α,2β,3aα,6aα)-Octahydro-1,5,5-trimethylpentalene-1,2-diol 在 lead(IV) acetate 作用下， 以 苯 为溶剂， 反应 0.25h， 以89%的产率得到cis-2-Acetyl-4,4-dimethylcyclopentaneacetaldehyde
  参考文献：
  名称：

  1,3-Elimination reactions of (3,4-epoxybutyl)stannanes. Approach to the synthesis of hirsutene

  摘要：

  An advanced tricyclic precursor of hirsutene (3) was prepared by a 1,3-elimination reaction of spirocyclic epoxy stannane 7b. Compound 7b was synthesized efficiently from hydroxycyclohexenone 8b by conjugate addition of [(CH3)3Sn]2CuLi, Wittig methylenation, and VO(acac)2-catalyzed epoxidation. Intermediate 8b was prepared in five steps from the known enone 9 in 18% overall yield. An improved synthesis makes compound 9 available in four efficient steps from keto ester 12.

  DOI：

  10.1021/jo00006a020
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 四丁基氟化铵 、 氨 、 lithium 、 间氯过氧苯甲酸 、 lithium iodide 、 叔丁醇 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.33h， 生成 (1α,2β,3aα,6aα)-Octahydro-1,5,5-trimethylpentalene-1,2-diol
  参考文献：
  名称：

  1,3-Elimination reactions of (3,4-epoxybutyl)stannanes. Approach to the synthesis of hirsutene

  摘要：

  An advanced tricyclic precursor of hirsutene (3) was prepared by a 1,3-elimination reaction of spirocyclic epoxy stannane 7b. Compound 7b was synthesized efficiently from hydroxycyclohexenone 8b by conjugate addition of [(CH3)3Sn]2CuLi, Wittig methylenation, and VO(acac)2-catalyzed epoxidation. Intermediate 8b was prepared in five steps from the known enone 9 in 18% overall yield. An improved synthesis makes compound 9 available in four efficient steps from keto ester 12.

  DOI：

  10.1021/jo00006a020