2,3-dimethyl-4-(2'-methylpropylidene)-2-cyclopenten-1-one | 135773-90-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-dimethyl-4-(2'-methylpropylidene)-2-cyclopenten-1-one
• 英文别名: (4E)-2,3-dimethyl-4-(2-methylpropylidene)cyclopent-2-en-1-one
• CAS: 135773-90-9
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: RMUBAHUCXOYSGX-BJMVGYQFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-甲基丁烷 、 山梨酸氯化物 在 三氯化铝 、 乙醇 作用下， 生成 2,3-dimethyl-4-(2'-methylpropyl)-2-cyclopenten-1-one 、 2,3-dimethyl-4-(2'-methylpropylidene)-2-cyclopenten-1-one
  参考文献：
  名称：

  Acylation of alkenes generated in situ by hydride transfer from isoalkanes. Synthesis of pentalenones, hydrindenones, and cyclopentenones

  摘要：

  Acylation, in the presence of AlCl3 and hydride acceptor, of methylcyclopentane, methylcyclohexane, and 2-methylbutane by ethylenic acyl chlorides, in CH2Cl2 solution, respectively, leads to tetrahydropentalenones, tetrahydroindenones, and cyclopentenones in good yields. Hydride acceptor may be either acetyl chloride or the alkenoyl chloride itself. Better results are performed in the presence of nitromethane and CuSO4. Overall yields are better than those obtained by the two-step process involving acylation of alkenes by alkenoyl chlorides and subsequent Nazarov cyclization of the resulting divinylketones. Methyl 1,4-migration is observed during the acylation of 2-methylbutane by sorboyl chloride. The mechanism of these conversions is discussed on the basis of results observed with cyclohexane-d12 and methylbutane-d6 as well as stereochemical studies of the cyclization process.

  DOI：

  10.1021/ja00021a036

文献信息

• Acylation of alkenes generated in situ by hydride transfer from isoalkanes. Synthesis of pentalenones, hydrindenones, and cyclopentenones
  作者：Christophe Morel-Fourrier、Jean Pierre Dulcere、Maurice Santelli

  DOI：10.1021/ja00021a036

  日期：1991.10

  Acylation, in the presence of AlCl3 and hydride acceptor, of methylcyclopentane, methylcyclohexane, and 2-methylbutane by ethylenic acyl chlorides, in CH2Cl2 solution, respectively, leads to tetrahydropentalenones, tetrahydroindenones, and cyclopentenones in good yields. Hydride acceptor may be either acetyl chloride or the alkenoyl chloride itself. Better results are performed in the presence of nitromethane and CuSO4. Overall yields are better than those obtained by the two-step process involving acylation of alkenes by alkenoyl chlorides and subsequent Nazarov cyclization of the resulting divinylketones. Methyl 1,4-migration is observed during the acylation of 2-methylbutane by sorboyl chloride. The mechanism of these conversions is discussed on the basis of results observed with cyclohexane-d12 and methylbutane-d6 as well as stereochemical studies of the cyclization process.