2-(4-methoxyphenylamino)cyclohexa-2,5-diene-1,4-dione | 33253-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-methoxyphenylamino)cyclohexa-2,5-diene-1,4-dione
• 英文别名: 2-(4-methoxyanilino)cyclohexa-2,5-diene-1,4-dione
• CAS: 33253-68-8
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: IIZURIKEGVOJDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲氧苯胺 、 对苯醌 以 乙醇 为溶剂， 生成 2-(4-methoxyphenylamino)cyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Iskander, M. L.; Medien, H. A. A.; Nashed, S., Zeitschrift fur Physikalische Chemie (Leipzig), 1988, vol. 269, # 6, p. 1183 - 1193

  摘要：

  DOI：

文献信息

• 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.
• Iskander, M. L.; Medien, H. A. A.; Nashed, S., Zeitschrift fur Physikalische Chemie (Leipzig), 1988, vol. 269, # 6, p. 1183 - 1193
  作者：Iskander, M. L.、Medien, H. A. A.、Nashed, S.

  DOI：——

  日期：——
• Green protocol for conjugate addition of amines to p-quinones accelerated by water
  作者：Jhillu S. Yadav、Basi V. Subba Reddy、Tallapally Swamy、Kattela Shiva Shankar

  DOI：10.1007/s00706-008-0917-1

  日期：2008.11

  Amines undergo smooth conjugate addition to p-quinones in H2O at ambient temperature in the absence of a catalyst to produce 2-aminoquinones in excellent yields. Significant rate acceleration of this reaction is observed in H2O compared to organic solvents. H2O played a dual role in simultaneously activating the p-quinone and amine. This new methodology constitutes an easy, highly efficient, and green synthesis of substituted p-quinones.