6-(1,2-dioxo-2-phenylethyl)-1,2,4,5-tetramethyl-3-(phenylethynyl)benzene | 140477-39-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 6-(1,2-dioxo-2-phenylethyl)-1,2,4,5-tetramethyl-3-(phenylethynyl)benzene
• 英文别名: 1-phenyl-2-[2,3,5,6-tetramethyl-4-(2-phenylethynyl)phenyl]ethanedione；6-(1,2-Dioxo-2-phenylethyl)-1,2,4,5-tetra-methyl-3-(phenylethynyl)benzene；1-phenyl-2-[2,3,5,6-tetramethyl-4-(2-phenylethynyl)phenyl]ethane-1,2-dione
• CAS: 140477-39-0
• 化学式: C₂₆H₂₂O₂
• 分子量: 366.459
• InChiKey: MJPGBIQLXOGAJA-UHFFFAOYSA-N

物化性质

• 沸点：
  565.1±50.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(1,2-dioxo-2-phenylethyl)-1,2,4,5-tetramethyl-3-(phenylethynyl)benzene 在 碘 、 氧气 作用下， 以 二甲基亚砜 为溶剂， 反应 23.0h， 以40%的产率得到1-(4-hydroxy-2,3,5,6-tetramethylphenyl)-2-phenylethanedione
  参考文献：
  名称：

  摘要：

  While heating 1,2,4,5-tetramethyl-3,6-bis(phenylethynyl)benzene, 1,3,5-trimethyl-2,4-bis(phenylethynyl)benzene, and 1,2,4,5-tetramethyl-3-(phenylethynyl)benzene with iodine in DMSO in the absence of oxygen, the triple bonds are oxidized to give the corresponding 1,2-diketones. In the presence of oxygen, the previously unknown competitive oxidative process causes the cleavage of the aryl-ethynyl bonds so that duroquinone and the corresponding 4-hydroxybenzils are formed. This cleavage is produced by oxygen only in the presence of iodine and DMSO. It was shown that the key stage of the process is the formation of intermediate charge-transfer complexes between polymethylbenzene rings and iodine.

  DOI：

  10.1023/a:1011329621330
• 作为产物：
  描述：

  1,2,4,5-四甲基-3,6-双(2'-苯乙烯基)苯 在 iodosophenyl trifluoroacetate 、 水 作用下， 以 氯仿 为溶剂， 以38%的产率得到6-(1,2-dioxo-2-phenylethyl)-1,2,4,5-tetramethyl-3-(phenylethynyl)benzene
  参考文献：
  名称：

  Karpitskaya, L. G.; Vasil'eva, V. P.; Merkushev, E. B., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 9.2, p. 1732 - 1736

  摘要：

  DOI：

文献信息

• Yusubov; Zholobova; Vasil'eva, Russian Journal of Organic Chemistry, 1996, vol. 32, # 8, p. 1233 - 1234
  作者：Yusubov、Zholobova、Vasil'eva、Habicher、Filimonov

  DOI：——

  日期：——
• ——
  作者：M. S. Yusubov、G. A. Zholobova、I. L. Filimonova、V. P. Vasil"eva、V. D. Filimonov、Ki-Whan Chi

  DOI：10.1023/a:1011329621330

  日期：——

  While heating 1,2,4,5-tetramethyl-3,6-bis(phenylethynyl)benzene, 1,3,5-trimethyl-2,4-bis(phenylethynyl)benzene, and 1,2,4,5-tetramethyl-3-(phenylethynyl)benzene with iodine in DMSO in the absence of oxygen, the triple bonds are oxidized to give the corresponding 1,2-diketones. In the presence of oxygen, the previously unknown competitive oxidative process causes the cleavage of the aryl-ethynyl bonds so that duroquinone and the corresponding 4-hydroxybenzils are formed. This cleavage is produced by oxygen only in the presence of iodine and DMSO. It was shown that the key stage of the process is the formation of intermediate charge-transfer complexes between polymethylbenzene rings and iodine.
• Karpitskaya, L. G.; Vasil'eva, V. P.; Merkushev, E. B., Journal of Organic Chemistry USSR (English Translation), 1991, vol. 27, # 9.2, p. 1732 - 1736
  作者：Karpitskaya, L. G.、Vasil'eva, V. P.、Merkushev, E. B.

  DOI：——

  日期：——