2,2'-diiodo-4,4'-dimethylazobenzene | 87005-22-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 2,2'-diiodo-4,4'-dimethylazobenzene
• 英文别名: (E)-1,2-bis(2-iodo-4-methylphenyl)diazene
• CAS: 87005-22-9
• 化学式: C₁₄H₁₂I₂N₂
• 分子量: 462.072
• InChiKey: LAQAVWAPXAGSJX-ISLYRVAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.93
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  24.72
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  氯化二苯基硅烷 、 2,2'-diiodo-4,4'-dimethylazobenzene 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 12.17h， 以70%的产率得到2,2'bis(diphenylsilyl)-4,4'-dimethylazobenzene
  参考文献：
  名称：

  Crucial Role of N···Si Interactions in the Solid-State Coloration of Disilylazobenzenes

  摘要：

  2.2'-Bis(fluorodiphensylsilyl)azobenzenes bearing two methyl and butyl groups at the 4- and 4'-positions were synthesized, and their X-ray crystallographic analyses revealed that they have tetracoordinated and pentacoordinated silicon atoms, respectively. Although the two compounds showed almost the same spectra in solution, the reflectance spectra of the solid revealed that the pentacoordinated state had a weaker absorbance in the long-wavelength region compared with that of the tetracoordinated state, which is ascribed to the shift of the n-pi* transition. This difference in the absorptions due to the n-pi* transition drastically affects the color of the azobenzenes: the color of the pentacoordinated state becomes apparently paler than that of the tetracoordinated state.

  DOI：

  10.1021/jo801334a
• 作为产物：
  描述：

  3-碘-4-甲基苯胺 在 manganese(IV) oxide 作用下， 反应 2.5h， 以45%的产率得到2,2'-diiodo-4,4'-dimethylazobenzene
  参考文献：
  名称：

  Crucial Role of N···Si Interactions in the Solid-State Coloration of Disilylazobenzenes

  摘要：

  2.2'-Bis(fluorodiphensylsilyl)azobenzenes bearing two methyl and butyl groups at the 4- and 4'-positions were synthesized, and their X-ray crystallographic analyses revealed that they have tetracoordinated and pentacoordinated silicon atoms, respectively. Although the two compounds showed almost the same spectra in solution, the reflectance spectra of the solid revealed that the pentacoordinated state had a weaker absorbance in the long-wavelength region compared with that of the tetracoordinated state, which is ascribed to the shift of the n-pi* transition. This difference in the absorptions due to the n-pi* transition drastically affects the color of the azobenzenes: the color of the pentacoordinated state becomes apparently paler than that of the tetracoordinated state.

  DOI：

  10.1021/jo801334a

文献信息

• Rh(<scp>iii</scp>)-Catalyzed regioselective mono- and di-iodination of azobenzenes using alkyl iodide
  作者：Jixing Li、Wenxia Cong、Zeng Gao、Jinlong Zhang、Huameng Yang、Gaoxi Jiang

  DOI：10.1039/c8ob00318a

  日期：——

  A new approach for highly regioselective iodination of azobenzenes with alkyl iodide as the iodinating reagent enabled by Rh-catalyzed oxidative C–H activation has been developed. By changing the oxidant, various mono- and di-iodinated azobenzenes were smoothly obtained in moderate to excellent yields, respectively. The preliminary mechanistic study reveals that the reaction process might undergo electrophilic

  已经开发出一种新的方法，该方法可通过烷基碘作为Rh催化的CH-H氧化活化而实现的碘化试剂，对偶氮苯进行高度区域选择性碘化。通过改变氧化剂，分别以中等至极好的收率平稳地获得了各种单碘和二碘化的偶氮苯。初步的机理研究表明，反应过程可能会被烷基碘和氧化剂原位生成的碘阳离子物种进行定向取代的邻位金属五元rhodocycle化合物的亲电取代。
• Merkushev, E. B.; Gulyaeva, N. E., Journal of Organic Chemistry USSR (English Translation), 1983, p. 1001 - 1002
  作者：Merkushev, E. B.、Gulyaeva, N. E.

  DOI：——

  日期：——
• MERKUSHEV, E. B.;GULYAEVA, N. E., ZH. ORGAN. XIMII, 1983, 19, N 5, 1120-1121
  作者：MERKUSHEV, E. B.、GULYAEVA, N. E.

  DOI：——

  日期：——