(E)-2-(4-Chlorophenyl)-3-(2-nitrophenyl)-2-propenoic acid | 10465-92-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-2-(4-Chlorophenyl)-3-(2-nitrophenyl)-2-propenoic acid
• 英文别名: (2E)-2-(4-chlorophenyl)-3-(2-nitrophenyl)prop-2-enoic acid；2-(4-chloro-phenyl)-3t-(2-nitro-phenyl)-acrylic acid；2-(4-Chlor-phenyl)-3t-(2-nitro-phenyl)-acrylsaeure；2-Nitro-α-(4-chlor-phenyl)-trans-zimtsaeure；alpha-[4-Chlorophenyl]-2-nitrocinnamic acid；(E)-2-(4-chlorophenyl)-3-(2-nitrophenyl)prop-2-enoic acid
• CAS: 10465-92-6
• 化学式: C₁₅H₁₀ClNO₄
• 分子量: 303.702
• InChiKey: CGQQZAUXFVBRMF-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-(4-Chlorophenyl)-3-(2-nitrophenyl)-2-propenoic acid 在 ammonium hydroxide 、 iron(II) sulfate 作用下， 以76%的产率得到(E)-3-(2-Aminophenyl)-2-(4-chlorophenyl)-2-propenoic acid
  参考文献：
  名称：

  Soluble Catalysts for Improved Pschorr Cyclizations

  摘要：

  Several improved catalysts for the Pschorr phenanthrene synthesis have been discovered; all are soluble substances which initiate free-radical reactions by electron donation and thereby shorten the reaction time and increase the yield. One technique with K4Fe(CN)(6) in water produced phenanthrene-9-carboxylic acid (6a) in 87% yield, but its application did not extend to substituted examples where the diazonium salt is less soluble in water. A more general procedure with ferrocene in acetone produced not only 6a but also substituted examples 6b-f in yields of 88-94%. A modification which avoids the isolation of diazonium salts was developed for occasional synthetic use.

  DOI：

  10.1021/jo00106a034
• 作为产物：
  描述：

  3t-(2-nitro-phenyl)-2-(4-nitro-phenyl)-acrylic acid 在 盐酸 、 ammonium hydroxide 、 乙醇 、 硫化氢 、 copper(l) chloride 作用下， 生成 (E)-2-(4-Chlorophenyl)-3-(2-nitrophenyl)-2-propenoic acid
  参考文献：
  名称：

  666.核间环化。第二部分 Pschorr反应在邻氨基-α-苯基肉桂酸的某些取代衍生物上的应用

  摘要：

  DOI：

  10.1039/jr9490003172

文献信息

• When Inhibitors Do Not Inhibit: Critical Evaluation of Rational Drug Design Targeting Chorismate Mutase from<i>Mycobacterium tuberculosis</i>
  作者：Steffi Munack、Vincent Leroux、Kathrin Roderer、Mats Ökvist、André van Eerde、Lise-Lotte Gundersen、Ute Krengel、Peter Kast

  DOI：10.1002/cbdv.201200322

  日期：2012.11

  development of new medication is structure‐guided design, combined with virtual screening or docking studies. Here, we report the results of a drug‐design project, which we based on a publication that claimed the structure‐guided discovery of several promising and highly active inhibitors targeting the secreted chorismate mutase (*MtCM) from Mycobacterium tuberculosis. We set out to further improve on these

  结核病 (TB) 是一种毁灭性疾病，每年夺去数百万人的生命。药物获取受阻或不依从，特别是在发展中国家，导致耐药性，进一步加剧了这种情况。由于目前的标准疗法已经使用了 50 多年，而且临床试验中只有少数新候选药物，因此迫切需要新的结核病药物。新药开发的一个强大工具是结构引导设计，结合虚拟筛选或对接研究。在这里，我们报告了一个药物设计项目的结果，该项目基于一份出版物，该出版物声称在结构引导下发现了几种有希望的高活性抑制剂，这些抑制剂靶向来自结核分枝杆菌的分泌型分支酸变位酶 (*MtCM)。我们着手进一步改进这些化合物并合成了一系列新的衍生物。令我们沮丧的是，在酶促测定中对这些分子的彻底评估表明，要求保护的先导化合物和任何合成的衍生物均未显示对 *MtCM 的任何抑制作用。
• Nylen, Chemische Berichte, 1920, vol. 53, p. 162
  作者：Nylen

  DOI：——

  日期：——
• NORDIFF E. A.; SAGGIOMO A. J.; TANABE KEIICHI; CHEN E. H.; SHINBO MASAFU;+, J. MED. CHEM. <JMCM-AR>, 1975, 18, NO 10, 1011-1019
  作者：NORDIFF E. A.、 SAGGIOMO A. J.、 TANABE KEIICHI、 CHEN E. H.、 SHINBO MASAFU、+

  DOI：——

  日期：——
• Soluble Catalysts for Improved Pschorr Cyclizations
  作者：Frederick W. Wassmundt、William F. Kiesman

  DOI：10.1021/jo00106a034

  日期：1995.1

  Several improved catalysts for the Pschorr phenanthrene synthesis have been discovered; all are soluble substances which initiate free-radical reactions by electron donation and thereby shorten the reaction time and increase the yield. One technique with K4Fe(CN)(6) in water produced phenanthrene-9-carboxylic acid (6a) in 87% yield, but its application did not extend to substituted examples where the diazonium salt is less soluble in water. A more general procedure with ferrocene in acetone produced not only 6a but also substituted examples 6b-f in yields of 88-94%. A modification which avoids the isolation of diazonium salts was developed for occasional synthetic use.
• 666. Internuclear cyclisation. Part II. The application of the Pschorr reaction to some substituted derivatives of o-amino-α-phenylcinnamic acid
  作者：D. H. Hey、John M. Osbond

  DOI：10.1039/jr9490003172

  日期：——