3,4-dimethylspiro[4.5]dec-2-en-1-one | 672295-28-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4-dimethylspiro[4.5]dec-2-en-1-one
• 英文别名: 3,4-Dimethylspiro[4.5]dec-2-en-1-one；1,2-dimethylspiro[4.5]dec-2-en-4-one
• CAS: 672295-28-2
• 化学式: C₁₂H₁₈O
• 分子量: 178.274
• InChiKey: UPTRKISELMCDFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-1-(2-Methyl-cyclohept-1-enyl)-but-2-en-1-one 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 3,4-dimethylspiro[4.5]dec-2-en-1-one 、 3,3a-dimethyl-3,3a,4,5,6,7-hexahydro-2H-azulen-1-one
  参考文献：
  名称：

  An Expeditious Nazarov Cyclization Strategy toward the Hydroazulene Core of Guanacastepene A

  摘要：

  The hydroazulene core of guanacastepene A has been synthesized in five steps from commercially available starting materials using a classical Nazarov cyclization to install the stereochemistry in the cyclopentanone diastereoselectively. In the presence or absence of Lewis bases, a hydroazulenone or a spirocyclic ketone generated via a novel Wagner-Meerwein rearrangement is obtained with excellent selectivity and yield.

  DOI：

  10.1021/ol036433z

文献信息

• An Expeditious Nazarov Cyclization Strategy toward the Hydroazulene Core of Guanacastepene A
  作者：Pauline Chiu、Shuoliang Li

  DOI：10.1021/ol036433z

  日期：2004.2.1

  The hydroazulene core of guanacastepene A has been synthesized in five steps from commercially available starting materials using a classical Nazarov cyclization to install the stereochemistry in the cyclopentanone diastereoselectively. In the presence or absence of Lewis bases, a hydroazulenone or a spirocyclic ketone generated via a novel Wagner-Meerwein rearrangement is obtained with excellent selectivity and yield.