5,5'-dinitrobiphenyl-2,2'-dicarboxylic acid | 92159-34-7

• 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: 5,5'-dinitrobiphenyl-2,2'-dicarboxylic acid
• 英文别名: 5,5'-dinitro-[1,1'-biphenyl]-2,2'-dicarboxylic acid；5,5'-Dinitro-diphensaeure；5,5'-dinitro-diphenic acid；5.5'-Dinitro-diphenyl-dicarbonsaeure-(2.2')；5,5'-Dinitrodiphenic acid；2-(2-carboxy-5-nitrophenyl)-4-nitrobenzoic acid
• CAS: 92159-34-7
• 化学式: C₁₄H₈N₂O₈
• 分子量: 332.226
• InChiKey: FLZMKJSAEULZSP-UHFFFAOYSA-N

物化性质

• 熔点：
  285-287 °C (decomp)
• 沸点：
  562.9±50.0 °C(Predicted)
• 密度：
  1.632±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 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：
  166
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,5'-dinitrobiphenyl-2,2'-dicarboxylic acid 在 乙酸酐 作用下， 生成 5,5'-dinitrodiphenic anhydride
  参考文献：
  名称：

  Pufahl, Chemische Berichte, 1929, vol. 62, p. 2819

  摘要：

  DOI：
• 作为产物：
  描述：

  2-碘-4-硝基苯甲酸甲酯 在 硫酸 、 铜 作用下， 生成 5,5'-dinitrobiphenyl-2,2'-dicarboxylic acid
  参考文献：
  名称：

  Pufahl, Chemische Berichte, 1929, vol. 62, p. 2819

  摘要：

  DOI：

文献信息

• 2,2′-Biaryldicarboxylate Synthesis via Electrocatalytic Dehydrogenative C–H/C–H Coupling of Benzoic Acids
  作者：Zhongyi Zeng、Jonas F. Goebel、Xianming Liu、Lukas J. Gooßen

  DOI：10.1021/acscatal.1c01127

  日期：2021.6.4

  catalysts. These compounds have been found to be conveniently accessible from benzoic acids via Rh-catalyzed electrooxidative C–H/C–H couplings, giving valuable dihydrogen as the byproduct. In an undivided cell with Pt electrodes, RhCl3·3H2O catalyzes the oxidative carboxylate-directed ortho-homocoupling of various aromatic acids with a current efficiency of 67%. The protocol is operationally simple, tolerates

  2,2'-二芳基二羧酸酯是生物活性化合物、功能材料和手性催化剂中的重要功能。已经发现这些化合物可以通过 Rh 催化的电氧化 C-H/C-H 偶联从苯甲酸中方便地获得，并提供有价值的二氢作为副产物。在带有 Pt 电极的未分割电池中，RhCl 3 ·3H 2 O以 67% 的电流效率催化各种芳香酸的氧化羧酸定向邻位均偶联。该协议操作简单，可以容忍多种功能组，并且不需要排除空气和水分。通过萘基-1-羧酸与丙烯酸或苯甲酸的交叉脱氢偶联的异二聚化也被证明是有效的。
• One-Pot Preparation of (<i>NH</i>)-Phenanthridinones and Amide-Functionalized [7]Helicene-like Molecules from Biaryl Dicarboxylic Acids
  作者：Takuya Murai、Yongning Xing、Mayu Kurokawa、Toshifumi Kuribayashi、Masanori Nikaido、Elghareeb E. Elboray、Shohei Hamada、Yusuke Kobayashi、Takahiro Sasamori、Takeo Kawabata、Takumi Furuta

  DOI：10.1021/acs.joc.1c02769

  日期：2022.5.6

  A one-pot transformation of biaryl dicarboxylic acids to (NH)-phenanthridinone derivatives based on a Curtius rearrangement and subsequent basic hydrolysis was developed. This method is also applicable for the preparation of optically active amide-functionalized [7]helicene-like molecules. Furthermore, aza[5]helicene derivatives with a phosphate moiety were isolated as a product of the Curtius rearrangement

  开发了基于 Curtius 重排和随后的碱性水解的联芳基二羧酸向 ( NH )-菲啶酮衍生物的一锅法转化。该方法也适用于光学活性酰胺官能化[7]类螺烯分子的制备。此外，在带有硫属元素原子的底物的情况下，具有磷酸盐部分的氮杂[5]螺烯衍生物被分离为 Curtius 重排步骤的产物。通过 X 射线衍射分析揭示了这些产品的立体结构，表明硫属元素键合和磷元素键合相互作用可能有助于它们的稳定性。进一步研究了类螺烯分子的构型稳定性及其手性。
• The Synthesis of Certain Local Anesthetics of the Biphenyl Series
  作者：Francis H. Case、Emil Koft

  DOI：10.1021/ja01847a042

  日期：1941.2
• Potential antitumor agents. 58. Synthesis and structure-activity relationships of substituted xanthenone-4-acetic acids active against the colon 38 tumor in vivo
  作者：Gordon W. Rewcastle、Graham J. Atwell、Bruce C. Baguley、Stephen B. Calveley、William A. Denny

  DOI：10.1021/jm00124a012

  日期：1989.4

  In a search for compounds related to flavoneacetic acid with activity against solid tumors, a series of methyl-, methoxy-, chloro-, nitro-, and hydroxy-substituted xanthenone-4-acetic acids have been synthesized and evaluated against subcutaneously implanted colon adenocarcinoma 38 in vivo, using a short-term histology assay as a primary screening system. A major goal of this work was to identify compounds with similar profiles of activity to that of flavoneacetic acid but of higher potency. The level of activity of the compounds appeared to depend more on the nature of the substituent than its positioning, in the order Cl greater than Me, OMe greater than NO2, OH. However, the potency of the compounds was related much more to the position rather than the nature of the substitution, with 5-substituted compounds being clearly the most dose potent. 5-Methylxanthenone-4-acetic acid has a similar level of activity to that of flavoneacetic acid in the test systems employed but is more than 7-fold as dose potent.
• Braeunling,H. et al., Chemische Berichte, 1967, vol. 100, p. 880 - 888
  作者：Braeunling,H. et al.

  DOI：——

  日期：——