2-甲基-4-亚甲基环丁烯酮 | 1335114-52-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-甲基-4-亚甲基环丁烯酮
• 英文名称: 2-methyl-4-methylenecyclobutenone
• 英文别名: 2-Methyl-4-methylidenecyclobut-2-en-1-one
• CAS: 1335114-52-7
• 化学式: C₆H₆O
• 分子量: 94.113
• InChiKey: GAGSCOYTMNQPLA-UHFFFAOYSA-N

物化性质

• 沸点：
  161.7±7.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  benzoic 2,5-dimethyl-3-furoic anhydride 550.0 ℃ 、1.33 Pa 条件下， 以60%的产率得到3,4,5-hexatrien-2-one
  参考文献：
  名称：

  Syntheses and Pyrolyses of Furan Analogues of α-Oxo-o-quinodimethanes. Formation of Methylenecyclobutenone and 1-Buten-3-yne via a Vinylcarbene–Cyclopropene Rearrangement

  摘要：

  Flash vacuum pyrolyses (FVP) of benzoic 2-methyl-3-furoic anhydride (12) and benzoic 3-methyl-2-furoic anhydride (13) at 550 degrees C and ca. 10(-2) Torr both give methylenecyclobutenone (16) and 1-buten-3-yne (17) as the main products. A mechanism involving generation of furan analogues of alpha-oxo-o-quinodimethane, 10 and 11, from FVP of 12 and 13, respectively, followed by elimination of a CO molecule to give the respective carbenes 34 and 36 is proposed. Carbenes 34 and 36 are interconvertible via a cyclopropene intermediate 35. A ring contraction from 36 will give 16, whereas a ring-opening of 34 followed by elimination of a CO molecule then leads to 17. The proposed mechanism is supported by substituent- and deuterium-labeling study on FVP of the derivatives of 12.

  DOI：

  10.1021/jo201743h

文献信息

• Syntheses and Pyrolyses of Furan Analogues of α-Oxo-<i>o</i>-quinodimethanes. Formation of Methylenecyclobutenone and 1-Buten-3-yne via a Vinylcarbene–Cyclopropene Rearrangement
  作者：Pen-Wen Tseng、Chen-Yu Kung、Hsing-Yin Chen、Chin-Hsing Chou

  DOI：10.1021/jo201743h

  日期：2011.10.21

  Flash vacuum pyrolyses (FVP) of benzoic 2-methyl-3-furoic anhydride (12) and benzoic 3-methyl-2-furoic anhydride (13) at 550 degrees C and ca. 10(-2) Torr both give methylenecyclobutenone (16) and 1-buten-3-yne (17) as the main products. A mechanism involving generation of furan analogues of alpha-oxo-o-quinodimethane, 10 and 11, from FVP of 12 and 13, respectively, followed by elimination of a CO molecule to give the respective carbenes 34 and 36 is proposed. Carbenes 34 and 36 are interconvertible via a cyclopropene intermediate 35. A ring contraction from 36 will give 16, whereas a ring-opening of 34 followed by elimination of a CO molecule then leads to 17. The proposed mechanism is supported by substituent- and deuterium-labeling study on FVP of the derivatives of 12.