2-硝基-联苯-4-羧酸甲酯 | 39180-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-硝基-联苯-4-羧酸甲酯
• 英文名称: 4-methoxycarbonyl-2-nitrobiphenyl
• 英文别名: methyl 2-nitro[1,1'-biphenyl]-4-carboxylate；3-Nitro-4-phenyl-benzoesaeure-methylester；2-Nitro-4-carbomethoxybiphenyl；2-nitro-biphenyl-4-carboxylic acid methyl ester；2-Nitro-biphenyl-4-carbonsaeure-methylester；methyl 2-nitrobiphenyl-4-carboxylate；methyl 3-nitro-4-phenylbenzoate
• CAS: 39180-36-4
• 化学式: C₁₄H₁₁NO₄
• mdl: MFCD09033504
• 分子量: 257.246
• InChiKey: QLBQDTHLYXLDOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2916399090

反应信息

• 作为反应物：
  描述：

  2-硝基-联苯-4-羧酸甲酯 在 叠氮磷酸二苯酯 、 水 、 三乙胺 、 三苯基膦 、 sodium hydroxide 作用下， 以 乙醇 、 邻二氯苯 、 叔丁醇 为溶剂， 反应 54.0h， 生成 9H-咔唑-2-胺
  参考文献：
  名称：

  Design, synthesis, and evaluation of potent Wnt signaling inhibitors featuring a fused 3-ring system

  摘要：

  The Wnt signaling pathway is a critical developmental pathway which operates through control of cellular functions such as proliferation and differentiation. Aberrant Wnt signaling has been linked to the formation and metastasis of tumors. Porcupine, a member of the membrane -bound O-acyltransferase family of proteins, is an important component of the Wnt pathway. Porcupine catalyzes the palmitoylation of Wnt proteins, a process needed for their secretion and activity. Here we report a novel series of compounds obtained by a scaffold hybridization strategy from a known porcupine inhibitor class. The leading compound 59 demonstrated subnanomolar inhibition of Wnt signaling in a paracrine cellular assay. Compound 59 also showed excellent chemical, plasma and liver microsomal stabilities. Furthermore, compound 59 exhibited good pharmacokinetic profiles with 30% oral bioavailability in rat. Collectively, these results strongly support further optimization of this novel scaffold to develop better Wnt pathway inhibitors. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.026
• 作为产物：
  描述：

  3-硝基-4-羟基苯甲酸甲酯 在 2,4,6-三甲基吡啶 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三(邻甲基苯基)磷 、 lithium chloride 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 2-硝基-联苯-4-羧酸甲酯
  参考文献：
  名称：

  Stille and Suzuki Cross Coupling Reactions of o-Nitrophenyl Triflates: A Versatile Route to a Variety of Heterocycles

  摘要：

  DOI：

  10.3987/com-98-8197

文献信息

• Synthesize, Characterization and Application of Phosphine-free Polymer Supported Palladium Nanoparticles as Effective Catalyst in Suzuki-Miyaura Cross-coupling Reactions
  作者：Hossein Mahdavi、Payam Hashemi

  DOI：10.1002/jccs.201200257

  日期：2013.4

  Heterogeneous catalysts were developed by supporting palladium nanoparticles on modified cross‐linked polyacrylamide and successfully applied in Suzuki‐Miyaura cross‐coupling reactions. These catalysts are stable to air and moisture, and no sign of metal leaching was detected during the reactions as judged by elemental analysis of palladium by ICP‐OES technique and hot filtration test, which demonstrates

  通过将钯纳米颗粒负载在改性的交联聚丙烯酰胺上开发出非均相催化剂，并将其成功应用于铃木宫浦的交叉偶联反应中。这些催化剂对空气和湿气稳定，通过ICP-OES技术和热过滤测试对钯进行元素分析可以判断反应期间没有金属浸出迹象，这证明了催化剂的非均相特性。通过在80°C以下的温度下使用这些无膦催化剂，而无需任何其他配体的辅助，可以实现所需产物的高收率。通过热重分析（TGA）证实了催化剂在操作温度下的热稳定性。这些催化剂易于使用且具有成本效益。可以通过简单的过滤将其从反应混合物中回收，然后再用于更多连续的反应中，而不会明显降低活性。失活10个循环后，通过超声程序恢复催化剂活性。
• Triphenylphosphine-Mediated Reductive Cyclization of 2-Nitrobiphenyls:  A Practical and Convenient Synthesis of Carbazoles
  作者：Adam W. Freeman、Marie Urvoy、Megan E. Criswell

  DOI：10.1021/jo0503299

  日期：2005.6.1

  The synthesis of a series of substituted carbazoles from the corresponding 2-nitrobiphenyl derivatives using a novel modification of the Cadogan reaction is described. Cyclization of the 2-nitrobiphenyls was achieved via reductive deoxygenation of the nitro groups using a slight excess of triphenylphosphine in a suitable solvent. We have observed a temperature dependence on the extent of conversion

  描述了使用Cadogan反应的新型修饰从相应的2-硝基联苯衍生物合成一系列取代的咔唑。2-硝基联苯的环化是通过在适当的溶剂中使用稍微过量的三苯膦通过硝基的还原性脱氧来实现的。我们已经观察到在这些条件下温度对转化率的依赖性，较高沸点的溶剂可在一系列底物上提供较高的收率。新的反应条件非常简单易行，可以耐受各种官能团，并在不存在不需要的副产物的情况下生成咔唑产物。
• Catalytic reductive cyclization of 2-nitrobiphenyls using phenyl formate as CO surrogate: A robust synthesis of 9H-carbazoles
  作者：Doaa R. Ramadan、Francesco Ferretti、Fabio Ragaini

  DOI：10.1016/j.jcat.2022.03.024

  日期：2022.5

  A palladium/phenanthroline catalyzed reductive cyclization of o-nitrobiphenyls to 9H-carbazoles operated by in situ released CO is described. In the present method, the presence of phenyl formate is essential to avoid the use of high-pressure equipment and allows to perform the reaction in a single thick-walled glass tube. The identity of the base, which catalyzes the formate decomposition, is crucial

  描述了通过原位释放的 CO操作的钯/菲咯啉催化的邻硝基联苯还原环化为 9 H-咔唑。在本方法中，甲酸苯酯的存在对于避免使用高压设备是必不可少的，并且允许在单个厚壁玻璃管中进行反应。催化甲酸盐分解的碱的特性对反应的选择性至关重要。催化剂的稳定性受氯阴离子存在的影响。咔唑产率通常高于之前报道的使用加压 CO 的产率。优化的催化系统具有出色的稳定性和耐湿性和耐空气性，可以在低催化剂负载下进行反应。
• ANTI-VIRAL COMPOUNDS
  申请人：Rockway W. Todd

  公开号：US20070232645A1

  公开（公告）日：2007-10-04

  Compounds effective in inhibiting replication of Hepatitis C virus (“HCV”) or other viruses are disclosed. This invention is also directed to compositions comprising such compounds, co-formulation or co-administration of such compounds with other anti-viral or therapeutic agents, processes and intermediates for the syntheses of such compounds, and methods of using such compounds for the treatment of HCV or other viral infections.

  本发明揭示了有效抑制丙型肝炎病毒（“HCV”）或其他病毒复制的化合物。本发明还涉及包含这种化合物的组合物、与其他抗病毒或治疗剂一起配方或共同管理这种化合物的组合物、用于合成这种化合物的过程和中间体，以及使用这种化合物治疗HCV或其他病毒感染的方法。
• Anti-viral compounds
  申请人：Abbott Laboratories

  公开号：US07763731B2

  公开（公告）日：2010-07-27

  Compounds effective in inhibiting replication of Hepatitis C virus (“HCV”) or other viruses are disclosed. This invention is also directed to compositions comprising such compounds, co-formulation or co-administration of such compounds with other anti-viral or therapeutic agents, processes and intermediates for the syntheses of such compounds, and methods of using such compounds for the treatment of HCV or other viral infections.

  本发明揭示了一种有效抑制丙型肝炎病毒（“HCV”）或其他病毒复制的化合物。该发明还涉及包含这种化合物的组合物、与其他抗病毒或治疗剂共同配方或共同管理这种化合物的组合物、用于合成这种化合物的过程和中间体，以及使用这种化合物治疗HCV或其他病毒感染的方法。