hexa-3c,5-dien-2-one | 42363-76-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: hexa-3c,5-dien-2-one
• 英文别名: cis-3,5-Hexadien-2-one；(3Z)-hexa-3,5-dien-2-one
• CAS: 42363-76-8
• 化学式: C₆H₈O
• 分子量: 96.1289
• InChiKey: DACOGBAZMZEGQL-PLNGDYQASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  hexa-3c,5-dien-2-one 在 三氟化硼乙醚 作用下， 以 氘代苯 为溶剂， 生成 1-乙酰基-1,3-丁二烯
  参考文献：
  名称：

  Lewis acid reversal of the torquoselectivity of the electrocyclic ring opening of 3-acetylcyclobutene

  摘要：

  Thermolysis of 3-acetylcyclobutene resulted in a mixture of E-and Z-dienes, favoring slightly the E-diene, in accord with theoretical prediction. This preference was reversed by the Lewis acid, ZnI2, also predicted by ab initio calculations on a model system.

  DOI：

  10.1016/s0040-4039(00)91766-0
• 作为产物：
  描述：

  3-氯环丁基甲酸 在 三氟化硼乙醚 、 potassium tert-butylate 、 sodium carbonate 、 碘甲烷 作用下， 以 氘代苯 、 水 、 二甲基亚砜 、 乙腈 为溶剂， 生成 hexa-3c,5-dien-2-one
  参考文献：
  名称：

  Lewis acid reversal of the torquoselectivity of the electrocyclic ring opening of 3-acetylcyclobutene

  摘要：

  Thermolysis of 3-acetylcyclobutene resulted in a mixture of E-and Z-dienes, favoring slightly the E-diene, in accord with theoretical prediction. This preference was reversed by the Lewis acid, ZnI2, also predicted by ab initio calculations on a model system.

  DOI：

  10.1016/s0040-4039(00)91766-0

文献信息

• Interplay of Theory and Experiment:  Reversal of the Torquoselectivity of the Electrocyclic Ring Opening of 3-Acetylcyclobutene by a Lewis Acid
  作者：Satomi Niwayama

  DOI：10.1021/jo951047j

  日期：1996.1.1

  Theoretical predictions, accompanied by firm experimental verification, are presented on the ''torquoselectivity'' of the thermal ring opening of 3-acetylcyclobutene (1). 3-Acetylcyclobutene was synthesized from commercially available 1,1-cyclobutanedicarboxylic acid. Thermolysis of 3-acetylcyclobutene resulted in a mixture of E- and Z-dienes with a slight preference for the E-diene. This preference was reversed by the Lewis acid, ZnI2, as predicted from theoretical calculations.
• Lewis acid reversal of the torquoselectivity of the electrocyclic ring opening of 3-acetylcyclobutene
  作者：Satomi Niwayama、K.N. Houk

  DOI：10.1016/s0040-4039(00)91766-0

  日期：1993.2

  Thermolysis of 3-acetylcyclobutene resulted in a mixture of E-and Z-dienes, favoring slightly the E-diene, in accord with theoretical prediction. This preference was reversed by the Lewis acid, ZnI2, also predicted by ab initio calculations on a model system.