1-crotonyl-2-methyl-1-cyclopentene | 135773-73-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-crotonyl-2-methyl-1-cyclopentene
• 英文别名: 1-(2-methylcyclopentenyl)-(E)-2-buten-1-one；(E)-1-(2-methylcyclopenten-1-yl)but-2-en-1-one
• CAS: 135773-73-8
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: WVKKHPWXFPDDAZ-HWKANZROSA-N

物化性质

• 沸点：
  234.0±10.0 °C(Predicted)
• 密度：
  0.963±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• 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：

  1-crotonyl-2-methyl-1-cyclopentene 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以40%的产率得到3,3-dimethyl-4,5,6-trihydro-2H-pentalen-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
• 作为产物：
  描述：

  2-丁烯酰氯 、 1-甲基环戊烯 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以65%的产率得到1-crotonyl-2-methyl-1-cyclopentene
  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

• Formation of 2-cyclohexenones by friedel-crafts acylation of alkenes with β,γ-ethylenic acyl halides
  作者：Robert Faure、Agnès Pommier、Jean-Marc Pons、Michel Rajzmann、Maurice Santelli

  DOI：10.1016/s0040-4020(01)86590-x

  日期：1992.9

  Friedel-Crafts acylation of alkenes with beta,gamma-alkenoyl halides leads to conjugated Al-trienolates able to cyclize into Al-enolates of 2-cyclohexenones through an allowed thermal disrotatory electrocyclization mechanism. Discussion of the product structure is based on two-dimensional NMR experiments (400 MHz) and molecular mechanics studies (GENMOL and MM2).
• BOUNKHALA Z.; HACINI S.; PARDO R.; SANTELLI M., J. CHEM. SOC. CHEM. COMM., 1979, NO 6, 263
  作者：BOUNKHALA Z.、 HACINI S.、 PARDO R.、 SANTELLI M.

  DOI：——

  日期：——
• 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.