2-((9,10-dioxo-9,10-dihydroanthracen-1-yl)diazenyl)-5-hydroxybenzoic acid | 1295623-03-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 2-((9,10-dioxo-9,10-dihydroanthracen-1-yl)diazenyl)-5-hydroxybenzoic acid
• CAS: 1295623-03-8
• 化学式: C₂₁H₁₂N₂O₅
• 分子量: 372.337
• InChiKey: IKUZCAWBGVSOKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  116.39
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-((9,10-dioxo-9,10-dihydroanthracen-1-yl)diazenyl)-5-hydroxybenzoic acid 、 5-(p-aminophenyl)-10,15,20-triphenylporphine 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以45%的产率得到
  参考文献：
  名称：

  The synthesis of porphyrin–anthraquinone dyad via an azo-rearrangement

  摘要：

  One novel porphyrin P-Q2 is planned to be synthesized by condensation between ATPP and Q1. However, after separation by chromatography and characterization with JR. (1)H NMR, HR-MS and X-ray, P-Q1 is obtained unexpectedly. Compared the structure of P-Q1 with that of P-Q2, it is realized that an intramolecular cyclization rearrangement takes place when the azo group is situated in the o-position to the amido group. This rearrangement offers a new way to prepare indazole heterocycle. In addition, the spectral properties of P-Q1 have been studied by UV-vis and steady state fluorescence spectroscopy. Strong fluorescence quenching is observed in the preliminary emission spectrum due to the proposed electron transfer from the excited porphyrin to the anthraquinone moieties. (c) 2010 Ya Qing Feng. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2010.11.031
• 作为产物：
  描述：

  氨基-9,10-蒽二酮 、 间羟基苯甲酸 在 盐酸 、 sodium nitrite 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 7.0h， 以76%的产率得到2-((9,10-dioxo-9,10-dihydroanthracen-1-yl)diazenyl)-5-hydroxybenzoic acid
  参考文献：
  名称：

  A New Route to Indazolone via Amidation Reaction of o-Carboxyazobenzene

  摘要：

  One new route for the synthesis of amino-substituted indazol-3,5-dione via the amidation reaction of o-carboxyazobenzenes is reported. Optimization which includes effects of the solvents, molar ratio of starting materials, and dehydrating agents on this reaction has been studied. A possible reaction mechanism has been proposed on the basis of the product's structure, and the steric hindrance could be the main reason for low yield.

  DOI：

  10.1021/ol203020x