5-chloro-7,7a-dihydro-7a-methyl-1(2H)-indenone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-chloro-7,7a-dihydro-7a-methyl-1(2H)-indenone
• 英文别名: 5-chloro-7a-methyl-6,7-dihydro-2H-inden-1-one
• 化学式: C₁₀H₁₁ClO
• 分子量: 182.65
• InChiKey: AQWJJUDMCVIHSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  2-methyl-2-(3-butynyl)-1,3-cyclopentanedione 在 三氟化硼乙醚 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以10%的产率得到5-chloro-7,7a-dihydro-7a-methyl-1(2H)-indenone
  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

文献信息

• Additive and Medium Effects on Lewis Acid-Promoted Cationic .pi.-Cyclizations of Alkenyl- and Alkynylcyclopentane-1,3-diones
  作者：Aaron Balog、Steven V. Geib、Dennis P. Curran

  DOI：10.1021/jo00107a012

  日期：1995.1

  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.