2,5-Bis-(N-methyl-anilino)-benzochinon-(1.4) | 3421-19-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,5-Bis-(N-methyl-anilino)-benzochinon-(1.4)
• 英文别名: 2,5-Bis--1,4-benzochinon；2,5-Bis--benzo-1,4-chinon；2,5-bis-(N-methyl-anilino)-[1,4]benzoquinone；2,5-Bis-(N-methyl-anilino)-[1,4]benzochinon；2,5-bis(N-methylanilino)cyclohexa-2,5-diene-1,4-dione
• CAS: 3421-19-0
• 化学式: C₂₀H₁₈N₂O₂
• 分子量: 318.375
• InChiKey: JCMUIZYDLCAUAM-UHFFFAOYSA-N

物化性质

• 熔点：
  205 °C
• 沸点：
  454.2±45.0 °C(Predicted)
• 密度：
  1.278±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-甲基苯胺 、 对苯醌 在 In(OSO₂CF₃)3 作用下， 以 水 为溶剂， 反应 2.0h， 以65%的产率得到2,5-Bis-(N-methyl-anilino)-benzochinon-(1.4)
  参考文献：
  名称：

  芳基取代的1,4-苯醌的合成通过水促进和（OTF）3催化的原位芳香族化合物的共轭加成-脱氢-1,4-苯醌在水

  摘要：

  单和二芳基取代的1,4-醌是通过In（OTf）3催化的芳香族C-亲核试剂与1,4-醌衍生物的共轭加成反应，然后在水中进行原位脱氢而合成的。发现水对反应有利。还检查了加成反应在水中的区域选择性。

  DOI：

  10.1002/adsc.200505248

文献信息

• Moehlau; Redlich, Chemische Berichte, 1911, vol. 44, p. 3615
  作者：Moehlau、Redlich

  DOI：——

  日期：——
• Synthesis of 3-[(N-carboalkoxy)ethylamino]-indazole-dione derivatives and their biological activities on human liver carbonyl reductase
  作者：Solomon Berhe、Andrew Slupe、Choice Luster、Henry A. Charlier、Don L. Warner、Leon H. Zalkow、Edward M. Burgess、Nkechi M. Enwerem、Oladapo Bakare

  DOI：10.1016/j.bmc.2009.11.011

  日期：2010.1

  A series of indazole-dione derivatives were synthesized by the 1,3-dipolar cycloaddition reaction of appropriate substituted benzoquinones or naphthoquinones and N-carboalkoxyamino diazopropane derivatives. These compounds were evaluated for their effects on human carbonyl reductase. Several of the analogs were found to serve as substrates for carbonyl reductase with a wide range of catalytic efficiencies, while four analogs display inhibitory activities with IC50 values ranging from 3-5 mu M. Two of the inhibitors were studied in greater detail and were found to be noncompetitive inhibitors against both NADPH and menadione with K-I values ranging between 2 and 11 mu M. Computational studies suggest that conformation of the compounds may determine whether the indazole-diones bind productively to yield product or nonproductively to inhibit the enzyme. (C) 2009 Elsevier Ltd. All rights reserved.
• Suida,H.; Suida,W., Justus Liebigs Annalen der Chemie, 1918, vol. 416, p. 160
  作者：Suida,H.、Suida,W.

  DOI：——

  日期：——
• Synthesis of Aryl-Substituted 1,4-Benzoquinonevia Water-Promoted and In(OTf)3-Catalyzedin situ Conjugate Addition-Dehydrogenation of Aromatic Compounds to 1,4-Benzoquinone in Water
  作者：Hai-Bo Zhang、Li Liu、Yong-Jun Chen、Dong Wang、Chao-Jun Li

  DOI：10.1002/adsc.200505248

  日期：2006.1

  Mono- and diaryl-substituted 1,4-quinones were synthesized by the In(OTf)3-catalyzed conjugate addition of aromatic C-nucleophiles to 1,4-quinone derivatives followed by in situ dehydrogenation in water. Water was found to be beneficial to the reaction. The regioselectivity of the addition reaction in water was also examined.

  单和二芳基取代的1,4-醌是通过In（OTf）3催化的芳香族C-亲核试剂与1,4-醌衍生物的共轭加成反应，然后在水中进行原位脱氢而合成的。发现水对反应有利。还检查了加成反应在水中的区域选择性。