2,3,4,4,5-Pentamethyl-2-cyclopentenon | 50506-54-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2,3,4,4,5-Pentamethyl-2-cyclopentenon
• 英文别名: 2-Cyclopenten-1-one, pentamethyl-；2,3,4,4,5-pentamethylcyclopent-2-en-1-one
• CAS: 50506-54-2
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: BHAMDTCJAVXQHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  2,3,4,4,5-Pentamethyl-2-cyclopentenon 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 1-methoxy-4-(2,3,3,4,5-pentamethyl-cyclopenta-1,4-dienyl)-benzene
  参考文献：
  名称：

  新型供体-受体降冰片二烯衍生物的合成

  摘要：

  新的供体-受体降冰片二烯衍生物 (NBD) 是由甲氧基苯基五甲基环戊二烯与含有吸电子基团的乙炔衍生物的 Diels-Alder 反应合成的。这些 NBD 衍生物在可见光区具有吸收作用，并经过光异构化处理，得到热稳定的四环烷衍生物 (QC)，具有相当的耐久性。

  DOI：

  10.1246/cl.2003.754
• 作为产物：
  描述：

  (E)-2-甲基-2-丁烯酰氯 、 2-甲基丁烷 在 三氯化铝 作用下， 生成 2,3,4,4,5-Pentamethyl-2-cyclopentenon
  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.
• Synthesis of New Donor–Acceptor Norbornadiene Derivatives
  作者：Takabumi Nagai、Ikuko Takahashi、Tadatomi Nishikubo

  DOI：10.1246/cl.2003.754

  日期：2003.8

  New donor–acceptor norbornadiene derivatives (NBDs) were synthesized from Diels–Alder reaction of methoxyphenylpentamethylcyclopendadiene with acetylene derivatives containing electron-withdrawing groups. These NBD derivatives have absorption in the visible region and photoisomerized to give thermally stable quadricyclane derivatives (QCs) with fair durability.

  新的供体-受体降冰片二烯衍生物 (NBD) 是由甲氧基苯基五甲基环戊二烯与含有吸电子基团的乙炔衍生物的 Diels-Alder 反应合成的。这些 NBD 衍生物在可见光区具有吸收作用，并经过光异构化处理，得到热稳定的四环烷衍生物 (QC)，具有相当的耐久性。