1,2,4,5-四甲基-3-(2-苯基乙炔基)苯 | 148101-03-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,2,4,5-四甲基-3-(2-苯基乙炔基)苯
• 英文名称: 1,2,4,5-tetramethyl-3-(phenylethynyl)benzene
• 英文别名: Benzene, 1,2,4,5-tetramethyl-3-(phenylethynyl)-；1,2,4,5-tetramethyl-3-(2-phenylethynyl)benzene
• CAS: 148101-03-5
• 化学式: C₁₈H₁₈
• 分子量: 234.341
• InChiKey: WCQMSEHUKUGJFM-UHFFFAOYSA-N

物化性质

• 沸点：
  386.2±42.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,2,4,5-四甲基-3-(2-苯基乙炔基)苯 在 碘 、 氧气 作用下， 以 二甲基亚砜 为溶剂， 反应 8.0h， 以63%的产率得到杜醌
  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：

  1,3,5-trimethyl-2,4-bis(phenylethynyl)benzene 在 碘 、 氧气 作用下， 以 二甲基亚砜 为溶剂， 反应 41.0h， 以21%的产率得到1,2,4,5-四甲基-3-(2-苯基乙炔基)苯
  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

文献信息

• Photochemical azido ligand transfer reaction of a triarylbismuth diazide with alkynes
  作者：Hitomi Suzuki、Chie Nakaya、Yoshihiro Matano

  DOI：10.1016/s0040-4039(00)77490-9

  日期：1993.2

  Irradiation of a triarylbismuth diazide in benzene in the presence of alkynes results in the transfer of one of the azido ligands to the triple bond, leading to N-unsubstituted 1,2,3-triazoles in fair to moderate yields.

  在炔烃的存在下在苯中照射三芳基铋二叠氮化物会导致叠氮配体之一转移到三键上，从而以中等至中等的收率得到N-未取代的1,2,3-三唑。
• Vasil'ev; Rudenko, Russian Journal of Organic Chemistry, 1997, vol. 33, # 11, p. 1555 - 1584
  作者：Vasil'ev、Rudenko

  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.