2-Methyl-2,5-heptadien-4-one-6,7,7,7-d4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Methyl-2,5-heptadien-4-one-6,7,7,7-d4
• 英文别名: (2E)-1,1,1,2-tetradeuterio-6-methylhepta-2,5-dien-4-one
• 化学式: C₈H₁₂O
• 分子量: 128.151
• InChiKey: NDIQNZBBNBMLMR-KLINVVBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  2-Methyl-2,5-heptadien-4-one-6,7,7,7-d4 在 硫酸 作用下， 反应 6.0h， 生成 5-Deuterio-4,4-dimethyl-3-(trideuteriomethyl)cyclopent-2-en-1-one 、 5-Deuterio-3,4-dimethyl-4-(trideuteriomethyl)cyclopent-2-en-1-one
  参考文献：
  名称：

  Nazarov reaction of trisubstituted dienones: mechanism involving Wagner-Meerwein shift

  摘要：

  The Nazarov reactions of trisubstituted alpha,alpha'-dienones were studied. Whereas alpha,beta-dimethyl-beta'-alkyl alpha,alpha'-dienones gave 2,3-dimethyl-4-alkyl-2-cyclopentenones when heated in concentrated sulfuric acid, the reaction of beta,beta-dimethyl-beta'-alkyl alpha,alpha'-dienones afforded 3,4-dimethyl-4-alkyl-2-cyclopentenones as the rearranged products. A mechanistic investigation using two deuterated dienones suggests that the Nazarov reactions of the latter dienones are accompanied by Wagner-Meerwein shifts to form the most stable carbocations.

  DOI：

  10.1021/jo00002a047
• 作为产物：
  描述：

  乙醛-d4 、 Dimethyl (4-Methyl-2-oxo-3-pentenyl)phosphonate 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 1.0h， 以47%的产率得到2-Methyl-2,5-heptadien-4-one-6,7,7,7-d4
  参考文献：
  名称：

  Nazarov reaction of trisubstituted dienones: mechanism involving Wagner-Meerwein shift

  摘要：

  The Nazarov reactions of trisubstituted alpha,alpha'-dienones were studied. Whereas alpha,beta-dimethyl-beta'-alkyl alpha,alpha'-dienones gave 2,3-dimethyl-4-alkyl-2-cyclopentenones when heated in concentrated sulfuric acid, the reaction of beta,beta-dimethyl-beta'-alkyl alpha,alpha'-dienones afforded 3,4-dimethyl-4-alkyl-2-cyclopentenones as the rearranged products. A mechanistic investigation using two deuterated dienones suggests that the Nazarov reactions of the latter dienones are accompanied by Wagner-Meerwein shifts to form the most stable carbocations.

  DOI：

  10.1021/jo00002a047

文献信息

• Nazarov reaction of trisubstituted dienones: mechanism involving Wagner-Meerwein shift
  作者：Jiro Motoyoshiya、Toshikazu Yazaki、Sadao Hayashi

  DOI：10.1021/jo00002a047

  日期：1991.1

  The Nazarov reactions of trisubstituted alpha,alpha'-dienones were studied. Whereas alpha,beta-dimethyl-beta'-alkyl alpha,alpha'-dienones gave 2,3-dimethyl-4-alkyl-2-cyclopentenones when heated in concentrated sulfuric acid, the reaction of beta,beta-dimethyl-beta'-alkyl alpha,alpha'-dienones afforded 3,4-dimethyl-4-alkyl-2-cyclopentenones as the rearranged products. A mechanistic investigation using two deuterated dienones suggests that the Nazarov reactions of the latter dienones are accompanied by Wagner-Meerwein shifts to form the most stable carbocations.