3-(4-Oxo-pentyl)-cyclopent-2-enone | 220084-71-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(4-Oxo-pentyl)-cyclopent-2-enone
• 英文别名: 3-(4-Oxopentyl)cyclopent-2-en-1-one
• CAS: 220084-71-9
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: QIXOBKAUGPBQCD-UHFFFAOYSA-N

物化性质

• 沸点：
  298.956±29.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.034±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-Oxo-pentyl)-cyclopent-2-enone 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以12%的产率得到Spiro[4.5]decane-2,7-dione
  参考文献：
  名称：

  Asymmetric spirocyclization: A new type of acid-catalyzed intramolecular 1, 4-addition to form carba-spirocyclic compounds

  摘要：

  Novel spirocyclization based on intramolecular 1,4-addition and its asymmetric version have been developed using a combination of Lewis acid and 1,2-diol. Treatment of five- and six-membered alpha,beta-unsaturated cyclic ketones having a 4-oxopentyl group at the beta-position with Lewis acid and ethylene glycol gave spiro[4.5]decane-2,7-dione and spiro[5.5]undecane-2,8-dione, respectively. The asymmetric version of this reaction has been developed by using optically active 1,2-diol such as cyclohexane-1,2-diol to afford the spirocyclic products of up to 85% e.e. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01009-6
• 作为产物：
  描述：

  3-(pent-4-en-1-yl)cyclopent-2-en-1-one 在 氧气 、 copper(l) chloride 、 palladium dichloride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以70%的产率得到3-(4-Oxo-pentyl)-cyclopent-2-enone
  参考文献：
  名称：

  Asymmetric spirocyclization: A new type of acid-catalyzed intramolecular 1, 4-addition to form carba-spirocyclic compounds

  摘要：

  Novel spirocyclization based on intramolecular 1,4-addition and its asymmetric version have been developed using a combination of Lewis acid and 1,2-diol. Treatment of five- and six-membered alpha,beta-unsaturated cyclic ketones having a 4-oxopentyl group at the beta-position with Lewis acid and ethylene glycol gave spiro[4.5]decane-2,7-dione and spiro[5.5]undecane-2,8-dione, respectively. The asymmetric version of this reaction has been developed by using optically active 1,2-diol such as cyclohexane-1,2-diol to afford the spirocyclic products of up to 85% e.e. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01009-6