(E)-2-Methyl-2,5-nonadien-4-one | 131794-40-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-2-Methyl-2,5-nonadien-4-one
• 英文别名: 2-methyl-nona-2,5t-dien-4-one；2-Methyl-nona-2,5t-dien-4-on；(5E)-2-methylnona-2,5-dien-4-one
• CAS: 131794-40-6
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: BWGIWZKLLQXYGX-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• 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

• 作为反应物：
  描述：

  (E)-2-Methyl-2,5-nonadien-4-one 在 硫酸 作用下， 以39%的产率得到4-Propyl-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：

  草酸 以74%的产率得到
  参考文献：
  名称：

  AXMEDOV, SH. T.;KURBANOV, S. B.;GYULAXMEDOV, L. M.;KURBANOVA, G. S., DOKL. AN AZSSR, 43,(1987) N 9, S. 40-45

  摘要：

  DOI：

文献信息

• Base-Catalyzed Condensations of Aldehydes with α,β-Unsaturated Ketones¹
  作者：Sargent G. Powell、William J. Wasserman

  DOI：10.1021/ja01565a045

  日期：1957.4
• 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：——
• AXMEDOV, SH. T.;KURBANOV, S. B.;GYULAXMEDOV, L. M.;KURBANOVA, G. S., DOKL. AN AZSSR, 43,(1987) N 9, S. 40-45
  作者：AXMEDOV, SH. T.、KURBANOV, S. B.、GYULAXMEDOV, L. M.、KURBANOVA, G. S.

  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.