2-methyl-undeca-2,5t-dien-4-one | 131794-43-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-undeca-2,5t-dien-4-one
• 英文别名: (5E)-2-methylundeca-2,5-dien-4-one
• CAS: 131794-43-9
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: PIIVCKRAMDXLLL-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 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-undeca-2,5t-dien-4-one 在 硫酸 作用下， 以47%的产率得到4-Pentyl-3,4-dimethyl-2-cyclopentenone
  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：

  Dimethyl (4-Methyl-2-oxo-3-pentenyl)phosphonate 、 正己醛 在 potassium carbonate 作用下， 以 水 为溶剂， 以55%的产率得到2-methyl-undeca-2,5t-dien-4-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

文献信息

• Palladium-catalyzed reactions of acylzirconocene chloride with organic halides
  作者：Yuji Hanzawa、Nobuhito Tabuchi、Takeo Taguchi

  DOI：10.1016/s0040-4039(98)01287-8

  日期：1998.8

  Palladium-catalyzed reactions of nonanoylzirconocene chloride 1 with aryl halide, acid halides, and allylic halides gave the acylated compounds through a nucleophilic attack of an “unmasked” acyl anion in fair to excellent yields. In an analogous way, allylic acetate gave an acyl substituted product through the reaction of 1.

  钯催化的壬酰基锆茂金属氯化物1与芳基卤化物，酰基卤和烯丙基卤化物的反应，通过“未掩盖的”酰基阴离子的亲核攻击，以合理的产率获得了酰化的化合物。以类似的方式，乙酸烯丙酯通过1的反应得到酰基取代的产物。
• MOTOYOSHIYA, JIRO;YAZAKI, TOSHIKAZU;HAYASHI, SADAO, J. ORG. CHEM., 56,(1991) N, C. 735-740
  作者：MOTOYOSHIYA, JIRO、YAZAKI, TOSHIKAZU、HAYASHI, SADAO

  DOI：——

  日期：——
• 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.