2-苯基偶氮苯甲酰苯胺 | 7310-83-0

• 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: 2-苯基偶氮苯甲酰苯胺
• 英文名称: 2- benzoylaminoazobenzene
• 英文别名: 2-phenylazobenzanilide；benzoic acid-(2-phenylazo-anilide)；Benzoesaeure-(2-phenylazo-anilid)；2-Benzolazo-N-benzoyl-anilin；2-Benzamino-azobenzol；2-Phenyl-azo-N-benzoylanilin；N-(2-phenyldiazenylphenyl)benzamide
• CAS: 7310-83-0
• 化学式: C₁₉H₁₅N₃O
• 分子量: 301.348
• InChiKey: BOVZRISOBAOCNF-UHFFFAOYSA-N

物化性质

• 熔点：
  122 °C
• 沸点：
  405.4±28.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-苯基偶氮苯甲酰苯胺 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以84%的产率得到2-(苯基偶氮)苯胺
  参考文献：
  名称：

  Syntheses and Properties of 1-Methyl-3-phenylaminobenzimidazolium Salts, Models of DNA Adducts of N7-Arylaminodeoxyguanosinium Salt

  摘要：

  When arylaminating carcinogens are administered to cells, they mainly generate the C8-arylamino-2'-deoxyguanosine adduct in DNA. A mechanism for this was proposed in which N7-arylaminated 2'-deoxyguanosine acts as an intermediate; however, it remained unclear whether this is actually the case. To elucidate the mechanisms involved in the generation of this adduct, a series of 5-substituted 1-methylbenzimidazole derivatives were used as models of the imidazole moiety of 2'-deoxyguanosine. Syntheses of a series of 5-substituted (CH3, H, F, CF3, or NO2) 1-methyl-3-phenylaminobenzimidazolium salts (7) and their related compounds were carried out, and the chemical characteristics of these products were examined. Keating compound 7 at 80 degreesC for 48 h in H2O/MeOH provided 5-substituted 1-methyl-2-oxo-2,3-dihydrobenzimidazoles but only when this compound contained a CF3 or NO2 substituent. Compound 7 decomposed in alkaline media, and its rate of decomposition increased when this compound had a stronger electron-withdrawing substituent. The product obtained under these conditions was 4-substituted N-1-methyl-2-phenylazoaniline. On the other hand, when 1-methyl-3-(4-nitrophenylamino)benzimidazolium salt was treated under the same conditions as described above, it generated, a demethylated product, 1-(4-nitrophenylamino)benzimidazole, when heated in H2O/MeOH and N-1-formyl-N-1-methyl-2-phenylazoaniline when treated in alkaline media. When the chemical characteristics of 3-phenylamino and 3-amino groups were compared using 3-substituted 1-methyl-5-(trifluoromethyl)benzimidazole the 3-phenylamino derivative was found to be more reactive.

  DOI：

  10.1021/tx0000724
• 作为产物：
  描述：

  鄰硝苯甲醯胺苯 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 30.0h， 生成 2-苯基偶氮苯甲酰苯胺
  参考文献：
  名称：

  Syntheses and Properties of 1-Methyl-3-phenylaminobenzimidazolium Salts, Models of DNA Adducts of N7-Arylaminodeoxyguanosinium Salt

  摘要：

  When arylaminating carcinogens are administered to cells, they mainly generate the C8-arylamino-2'-deoxyguanosine adduct in DNA. A mechanism for this was proposed in which N7-arylaminated 2'-deoxyguanosine acts as an intermediate; however, it remained unclear whether this is actually the case. To elucidate the mechanisms involved in the generation of this adduct, a series of 5-substituted 1-methylbenzimidazole derivatives were used as models of the imidazole moiety of 2'-deoxyguanosine. Syntheses of a series of 5-substituted (CH3, H, F, CF3, or NO2) 1-methyl-3-phenylaminobenzimidazolium salts (7) and their related compounds were carried out, and the chemical characteristics of these products were examined. Keating compound 7 at 80 degreesC for 48 h in H2O/MeOH provided 5-substituted 1-methyl-2-oxo-2,3-dihydrobenzimidazoles but only when this compound contained a CF3 or NO2 substituent. Compound 7 decomposed in alkaline media, and its rate of decomposition increased when this compound had a stronger electron-withdrawing substituent. The product obtained under these conditions was 4-substituted N-1-methyl-2-phenylazoaniline. On the other hand, when 1-methyl-3-(4-nitrophenylamino)benzimidazolium salt was treated under the same conditions as described above, it generated, a demethylated product, 1-(4-nitrophenylamino)benzimidazole, when heated in H2O/MeOH and N-1-formyl-N-1-methyl-2-phenylazoaniline when treated in alkaline media. When the chemical characteristics of 3-phenylamino and 3-amino groups were compared using 3-substituted 1-methyl-5-(trifluoromethyl)benzimidazole the 3-phenylamino derivative was found to be more reactive.

  DOI：

  10.1021/tx0000724

文献信息

• Cu(II)-catalyzed aerobic oxidative amidation of azoarenes with amides
  作者：Gang Li、Xiaoting Chen、Xulu Lv、Chunqi Jia、Panpan Gao、Ya Wang、Suling Yang

  DOI：10.1007/s11426-017-9175-2

  日期：2018.6

  dehydrogenative amidation of azoarene using air as the terminal oxidant was developed. Various amides, such as arylamides, alkylamides, lactams, and imides, are all effective amidation reagents and provide the desired products in moderate to excellent yields. Notably, good yields can also be obtained on a gram-scale with this amidation reaction. In this protocol of azoarene amidation, the catalyst (Cu(OAc)2)

  提出了一种以空气为末端氧化剂的Cu（II）催化的偶氮芳烃脱氢酰胺化方法。各种酰胺，例如芳基酰胺，烷基酰胺，内酰胺和酰亚胺，都是有效的酰胺化试剂，并以中等至优异的产率提供所需的产物。值得注意的是，通过该酰胺化反应，也可以以克为单位获得良好的产率。在该偶氮芳族酰胺化方案中，催化剂（Cu（OAc）2）和氧化剂（空气）便宜且容易获得，并且该方法高效且原子经济。
• 一种2-胺基偶氮芳香化合物的制备方法
  申请人：安阳师范学院

  公开号：CN107619379A

  公开（公告）日：2018-01-23

  一种2‑胺基偶氮芳香化合物的制备方法，所述的2‑胺基偶氮芳香化合物采用式Ⅰ的结构偶氮芳香化合物与的胺反应制备得到，反应过程为：将偶氮芳香化合物、胺、催化剂以及溶剂直接加入反应装置中，所述的催化剂为醋酸铜；所述溶剂为苯或二甲苯或二者的混合物，偶氮苯的摩尔用量为胺摩尔数的1‑3倍，搅拌加热温度至100℃‑130℃，反应24小时，分离产物得到2‑胺基偶氮芳香化合物。本制备方法合成路线简单，而且原料价格低廉、收率高。
• 一种邻苯二胺的制备方法
  申请人：安阳师范学院

  公开号：CN109081788A

  公开（公告）日：2018-12-25

  一种邻苯二胺的制备方法，采用2‑胺基偶氮芳香化合还原制备，采用下列两种方式之一进行还原反应得到邻苯二胺，第一种方式为：将2‑胺基偶氮芳香化合物、金属、酸及溶剂直接加入反应装置中，所述的金属为铁或锌；所述酸为乙酸或盐酸；所述溶剂为甲醇或乙醇；室温反应24小时，分离产物得到产物邻苯二胺；第二种方式为催化加氢进行还原反应，同样得到邻苯二胺。本制备方法简单，反应条件温和，产生的对苯二胺类副产物少，收率高。
• Forrester,A.R. et al., Journal of the Chemical Society. Perkin transactions I, 1979, p. 637 - 642
  作者：Forrester,A.R. et al.

  DOI：——

  日期：——
• Witt,F.H., Chemische Berichte, 1912, vol. 45, p. 2381,2383
  作者：Witt,F.H.

  DOI：——

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