1,2,4-triaminobenzene N²,N⁴-diacetate | 25781-60-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,2,4-triaminobenzene N²,N⁴-diacetate
• 英文别名: N²,N⁴-diacetyl-1,2,4-triaminobenzene；N,N'-(4-amino-m-phenylene)-bis-acetamide；N,N'-(4-Amino-m-phenylen)-bis-acetamid；1-Amino-2.4-bis-acetamino-benzol；4-Amino-N.N'-diacetyl-m-phenylendiamin；N-(3-acetamido-4-aminophenyl)acetamide
• CAS: 25781-60-6
• 化学式: C₁₀H₁₃N₃O₂
• 分子量: 207.232
• InChiKey: BRKOUWMNFOLKBE-UHFFFAOYSA-N

物化性质

• 熔点：
  218 °C
• 沸点：
  402.9±35.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  84.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2,4-triaminobenzene N²,N⁴-diacetate 在 盐酸 作用下， 生成 5-氨基-2-甲基苯并咪唑
  参考文献：
  名称：

  Phillips, Journal of the Chemical Society, 1928, p. 174

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(3-乙酰氨基苯基)乙酰胺 在 异戊醇 、 硫酸 、 硝酸 、 铁粉 、 溶剂黄146 作用下， 生成 1,2,4-triaminobenzene N²,N⁴-diacetate
  参考文献：
  名称：

  Phillips, Journal of the Chemical Society, 1928, p. 174

  摘要：

  DOI：

文献信息

• Regioselective N-acetylation as a route of nitro-p-phenylenediamine metabolism by rat liver cytosol.
  作者：Mitsuo NAKAO、Yukiko GOTO、Yasuhiko MATSUKI、Akira HIRATSUKA、Tadashi WATABE

  DOI：10.1248/cpb.38.2561

  日期：——

  Regioselectivity in N-acetylation of nitro-p-phenylenediamine, a widely used hair dye component, by rat liver cytosolic N-acetyltransferases was studied in relation to its substituent effects on enzymatic N-acetylation of mono-substituted anilines. Nitro-p-phenylenediamine was acetylated specifically at the N4-position to afford the N4-monoacetate, a major urinary metabolite in the rat, when incubated with rat liver cytosol fortified with acetyl-coenzyme A. N1-Acetylation of nitro-p-phenylenediamine did not take place even when the N4-monoacetate was used as a substrate, suggesting a strong steric hindrance effect of the ortho nitro group on the enzymatic N1-acetylation. The steric hindrance effect of the nitro group on the cytosolic N-acetylation of the ortho amino group was revealed by a comparative study carried out by using aniline, three respective regioisomers of nitroanilines and phenylenediamines as model substrates. The comparative study also indicated the enzymatic N-acetylation of the mono-substituted anilines to be strongly influenced by the electronic effect of the substituents.Regioselective N-acetylation in the hepatic cytosol was also investigated with N1- and N4-monoacetates of 1, 2, 4-triaminobenzene. The monoacetates yielded the N1, N4-diacetate, another major urinary metabolite of the hair dye component, in the rat, without concomitant formation of the N2, N4-diacetate or the N1, N2, N4-triacetate. The triacetate was formed only from the N1, N2-diacetate in the enzymatic reactions. A comparative study, carried out by using N-mono-acetates of three regioisomeric phenylenediamines, indicated that the N-acetyl group had a potent steric hindrance effect on the primary amino group at the ortho position.Thus, the present in vitro study strongly suggested that the two major urinary metabolites, nitro-p-phenylenediamine N4-acetate and 1, 2, 4-triaminobenzene N1, N4-diacetate, of the hair dye component could be formed, at least in the rat liver, by the enzymatic N-acetylation of the corresponding amines.

  研究了大鼠肝细胞质N-乙酰转移酶对一种广泛使用的染发剂成分——硝基对苯二胺的N-乙酰化中的区域选择性，并与其取代基对单取代苯胺酶促N-乙酰化的影响进行了关联。硝基对苯二胺在与富含乙酰辅酶A的大鼠肝细胞质孵育时，特异性地在N4位进行乙酰化，生成N4-单乙酸盐，这是大鼠的主要尿代谢产物。即使在使用N4-单乙酸盐作为底物的情况下，硝基对苯二胺的N1-乙酰化仍未发生，这表明邻位硝基对酶促N1-乙酰化有很强的立体阻碍效应。通过使用苯胺、三个相应的硝基苯胺和苯二胺的区域异构体作为模型底物进行的比较研究揭示了硝基对邻位氨基的细胞质N-乙酰化的立体阻碍效应。该比较研究还表明，单取代苯胺的酶促N-乙酰化受取代基电子效应的强烈影响。 在肝细胞质中，对1, 2, 4-三氨基苯的N1-和N4-单乙酸盐进行了区域选择性N-乙酰化的研究。这些单乙酸盐在反应中生成N1, N4-二乙酸盐，这是染发剂成分在大鼠的另一个主要尿代谢产物，而没有同时形成N2, N4-二乙酸盐或N1, N2, N4-三乙酸盐。三乙酸盐仅在酶促反应中由N1, N2-二乙酸盐形成。通过使用三种区域异构体苯二胺的N-单乙酸盐进行的比较研究表明，N-乙酰基对邻位的一级氨基具有强大的立体阻碍效应。因此，本体外研究强烈表明，染发剂成分的两个主要尿代谢产物——硝基对苯二胺N4-乙酸盐和1, 2, 4-三氨基苯N1, N4-二乙酸盐，至少可以通过对应胺的酶促N-乙酰化在大鼠肝脏中形成。
• Goldstein; Vaymatchar, Helvetica Chimica Acta, 1928, vol. 11, p. 246
  作者：Goldstein、Vaymatchar

  DOI：——

  日期：——
• Phillips, Journal of the Chemical Society, 1928, p. 174
  作者：Phillips

  DOI：——

  日期：——