cis-4-(dimethylmethylidene)-3,3a,4,5,6,6a-hexahydro-6a-methyl-1(2H)-pentalenone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-4-(dimethylmethylidene)-3,3a,4,5,6,6a-hexahydro-6a-methyl-1(2H)-pentalenone
• 英文别名: (3aR,6aS)-6a-methyl-4-propan-2-ylidene-3,3a,5,6-tetrahydro-2H-pentalen-1-one
• 化学式: C₁₂H₁₈O
• 分子量: 178.274
• InChiKey: FYHCIHSODKFBCG-PWSUYJOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 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

• 作为反应物：
  描述：

  cis-4-(dimethylmethylidene)-3,3a,4,5,6,6a-hexahydro-6a-methyl-1(2H)-pentalenone 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到(3aS,6aS)-3a-Methyl-hexahydro-pentalene-1,4-dione
  参考文献：
  名称：

  萜烯到萜烯。（+）-α-榄香烯的立体和对映选择性合成，以及通向多用途二喹烷Chiron的短途路线

  摘要：

  报道了采用新策略由单萜（+）-柠檬烯和（+）-2-胡萝卜素合成倍半萜烯（+）-α-榄香烯的方法。

  DOI：

  10.1039/c39940002759
• 作为产物：
  描述：

  2-甲基-2-(4-甲基戊-3-烯基)-1,3-二氧戊环 在 三氟化硼乙醚 、 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 34.17h， 生成 cis-4-(dimethylmethylidene)-3,3a,4,5,6,6a-hexahydro-6a-methyl-1(2H)-pentalenone
  参考文献：
  名称：

  Additive and Medium Effects on Lewis Acid-Promoted Cationic .pi.-Cyclizations of Alkenyl- and Alkynylcyclopentane-1,3-diones

  摘要：

  The effects of nucleophilic additives, Lewis and Bronsted acids, and solvents on BF3.Et(2)O-promoted cationic pi-cyclizations of alkynyl- and alkenylcyclopentane-1,3-diones are reported. The rates and selectivities of alkynyl dione cyclizations were significantly effected by the addition of external nucleophiles or water, and the regioselectivity of cyclization was effected by the choice of reaction solvent. Cyclizations of alkenyl diones, which fail under standard non-nucleophilic conditions, were found to be successful in the presence of added nucleophiles or with Lewis acids other than BF3.Et(2)O. The usefulness of these cationic pi-cyclizations for producing bicyclic ring systems of various functionality was also explored.

  DOI：

  10.1021/jo00107a012