(E)-3-((4-chlorophenyl)diazenyl)-1,2-dimethyl-1H-indole | 1542217-54-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (E)-3-((4-chlorophenyl)diazenyl)-1,2-dimethyl-1H-indole
• 英文别名: (E)-3-(4-chlorophenyldiazenyl)-1,2-dimethyl-1H-indole
• CAS: 1542217-54-8
• 化学式: C₁₆H₁₄ClN₃
• 分子量: 283.76
• InChiKey: OQSOTPWLBHJRTA-VHEBQXMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.56
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.65
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1,2-二甲基吲哚 、 对氯苯胺 在 盐酸 、 sodium nitrite 、 sodium carbonate 作用下， 以 水 、 溶剂黄146 、 丙酸 为溶剂， 反应 3.0h， 以82%的产率得到(E)-3-((4-chlorophenyl)diazenyl)-1,2-dimethyl-1H-indole
  参考文献：
  名称：

  Phenylazoindole dyes 2: The molecular structure characterizations of new phenylazo indoles derived from 1,2-dimethylindole

  摘要：

  In this study, five new phenylazo indoles derived from 1,2-dimethylindole were synthesized and characterized to evaluate the substituent effects on the molecular structures and absorption spectra. Theoretical calculations were carried out by density functional theory. The experimental and theoretical results are compared. X-ray single-crystal diffraction analyses reveal that the dyes have similar planar molecular conformation between azo and aromatic/heteroaromatic ring units but dissimilar crystal packing. The analysis of the electronic spectra showed that the electron-withdrawing groups (-Cl and -CN) were more effective than the electron-donating groups (-CH3 and -OCH3). Dyes containing electron-donating groups do not show significant changes relative to the parent dye, whereas the absorption maxima move to longer wavelengths for dyes containing electron-withdrawing groups. In addition, the absorption maxima exhibit the little bathochromic shifts for each dye with the increasing dielectric constants of the solvents. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.dyepig.2013.11.019

文献信息

• Iodine-Catalyzed Diazenylation with Arylhydrazine Hydrochlorides in Air
  作者：Dinesh S. Barak、Shashikant U. Dighe、Ilesha Avasthi、Sanjay Batra

  DOI：10.1021/acs.joc.7b03149

  日期：2018.4.6

  A mild approach to diazenylation of active methylene compounds and N-heterocyclic compounds with arylhydrazine hydrochlorides in the presence of iodine under basic aerobic conditions was developed. The reaction could be executed either under heating or in the presence of blue LED light, though the latter condition was found to be relatively efficient. Presumably, the aryldiazene produced by oxidation

  在碱性好氧条件下，在碘的存在下，开发了一种温和的方法，用碘化肼盐酸盐将活性亚甲基化合物和N-杂环化合物二氮杂烯基化。该反应可以在加热下或在蓝色LED灯的存在下进行，尽管发现后者条件是相对有效的。据推测，由芳基肼盐酸盐的氧化反应制得的芳基二氮烯是在碘存在下由活性亚甲基化合物产生的自由基中间体的氮清除剂，以产生重氮化合物。介绍了该协议的范围和局限性。