N-(4-nitrophenyl)isonicotinamide | 16153-63-2

• 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: N-(4-nitrophenyl)isonicotinamide
• 英文别名: N-(4-nitrophenyl)pyridine-4-carboxamide
• CAS: 16153-63-2
• 化学式: C₁₂H₉N₃O₃
• 分子量: 243.222
• InChiKey: PVQRRDXIBBXIQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-nitrophenyl)isonicotinamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 0.03h， 生成 N-(4-((3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-yl)amino)phenyl)isonicotinamide
  参考文献：
  名称：

  [EN] AMINONAPTHOQUINONE COMPOUNDS AND PHARMACEUTICAL COMPOSITION FOR BLOCKING UBIQUITINATION-PROTEASOME SYSTEM IN DISEASES
  [FR] COMPOSÉ AMINO-NAPTHOQUINONE ET COMPOSITION PHARMACEUTIQUE BLOQUANT LE SYSTÈME UBIQUITINE-PROTÉASOME DANS DES MALADIES

  摘要：

  这项发明涉及一种新的化合物，具有低细胞毒性，用于阻断疾病中的泛素化-蛋白酶体系统。因此，这些化合物可用于治疗包括但不限于癌症、神经退行性疾病、炎症性疾病、自身免疫性疾病和代谢性疾病在内的疾病。

  公开号：

  WO2017014788A1
• 作为产物：
  描述：

  4-吡啶甲酰胺 、 对硝基氯苯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 为溶剂， 反应 18.0h， 以96%的产率得到N-(4-nitrophenyl)isonicotinamide
  参考文献：
  名称：

  Exploring Homogeneous Conditions for Mild Buchwald–Hartwig Amination in Batch and Flow

  摘要：

  Cross-couplings are among the most frequently used reactions in complex molecule synthesis. However, the requirement of stoichiometric base can cause challenges. Harsh, insoluble inorganic bases can lead to poor tolerance of sensitive functional groups, scale-up issues, and difficult adaptation to continuous flow platforms. Herein, we describe the use of high throughput experimentation to identify a number of conditions that enable Buchwald-Hartwig reactions to be carried out using readily available ligands (e.g., XantPhos) with DBU as a soluble, functional-group-tolerant, homogeneous base. Application of this system to diverse aminations in batch and flow are demonstrated, as is the translation of this technique to performing continuous Mizoroki-Heck and Sonogashira coupling reactions.

  DOI：

  10.1021/acs.oprd.0c00018

文献信息

• Effective Nitration of Anilides and Acrylamides by<i>tert</i>-Butyl Nitrite
  作者：Yi-fei Ji、Hong Yan、Qi-bai Jiang

  DOI：10.1002/ejoc.201403510

  日期：2015.3

  [10% Cu(NO3)(2)3H(2)O] nitration of anilides was developed by using TBN (tert-butyl nitrite) as a nitrating reagent to give the corresponding nitro-substituted aromatic products in good to excellent yields. The use of TBN also led to the selective nitration of acrylamides at room temperature to afford only the (E) isomer of the nitration product. A series of anilides and acrylamides with a broad array

  硝基化合物是合成有机化学和化学工业中的重要中间体。在此，以TBN（亚硝酸叔丁酯）为硝化试剂，开发了铜催化[10% Cu(NO3)(2)3H(2)O]硝化苯胺的高效硝化反应，得到相应的硝基取代芳烃产物。良好的产量。TBN 的使用还导致丙烯酰胺在室温下选择性硝化以仅提供硝化产物的 (E) 异构体。该程序对一系列具有广泛官能团的苯胺和丙烯酰胺具有良好的耐受性。该合成方法具有原料廉价、反应条件温和、反应速度快、收率高等优点。机理研究表明，一个硝基自由基，
• Structures and magnetic properties of one-dimensional polymers constructed with copper(II) salts and pyridinecarboxamide-type ligands
  作者：Chun-Hua Ge、Hui-Zhong Kou、Zhong-Hai Ni、Yun-Bo Jiang、Ai-Li Cui

  DOI：10.1016/j.ica.2005.09.044

  日期：2006.1

  has a coordination environment similar to 1 , but water molecules have not been found. Weak C–H⋯N hydrogen bonding and π–π interaction yield a 3D supramolecular network which is different from that of complex 1 . Complex 3 is a 1D polymeric chain in which Cu(II) ions are bridged by Cl − , and only CH/π interactions had been found. Magnetic measurements revealed antiferromagnetic properties of 1 , 3

  摘要组成为[[Cu（μ1,5 -dca）2（mppca）2]·H 2 O} n（1），[Cu（μ1,5 -dca）2（nppca）2] n的三种配合物（2）和[Cu（μ-Cl）2（mppca）2] n（3）（dca =双氰胺，N（CN）2-; mppca = N-（4'-甲基苯基）-4-吡啶甲酰胺; nppca = N-（4'-硝基苯基）-4-吡啶甲酰胺已合成并通过单晶X射线晶体学和磁化率研究进行了表征。通过结晶固体中的不同非共价基序已经构建了复合物的不同超分子结构。在络合物1中，相邻的铜（II）原子通过双μ1,5 -dca（端对端）桥连接以形成链状结构。这些链通过π-π相互作用和配体与水分子之间的氢键相连，形成3D网络。在复数2中，铜（II）原子的配位环境与1相似，但未发现水分子。弱的C–H⋯N氢键和π–π相互作用产生3D超分子网络，与络合物1不同。配合物3是一维聚合物链，其中Cu（II）离子被Cl-桥接，并且仅发现CH
• Pyridinium cationic-dimer antimalarials, unlike chloroquine, act selectively between the schizont stage and the ring stage of Plasmodium falciparum
  作者：Mai Yoshikawa、Kazunori Motoshima、Kanji Fujimoto、Akihiro Tai、Hiroki Kakuta、Kenji Sasaki

  DOI：10.1016/j.bmc.2008.04.051

  日期：2008.6

  Malaria is a leading cause of death in developing countries, and the emergence of strains resistant to the main therapeutic agent, chloroquine, has become a serious problem. We have developed cationic-dimer type antimalarials, MAP-610 and PMAP-H10, which are structurally different from chloroquine. In this study, we introduced several substituents on the terminal phenyl rings of PMAP-H10. The electronic and hydrophobic properties of the substituents were correlated with the antimalarial activity and cytotoxicity of the compounds, respectively. Studies with synchronized cultures of malarial plasmodia showed that our cationic-dimers act selectively between the schizont stage and the ring stage of the parasitic cycle, unlike chloroquine, which has a stage-independent action. Thus, the mechanism of action of our antimalarials appears to be different from that of chloroquine, and our compounds may be effective against chloroquine-resistant strains. (C) 2008 Published by Elsevier Ltd.
• [EN] AMINONAPTHOQUINONE COMPOUNDS AND PHARMACEUTICAL COMPOSITION FOR BLOCKING UBIQUITINATION-PROTEASOME SYSTEM IN DISEASES<br/>[FR] COMPOSÉ AMINO-NAPTHOQUINONE ET COMPOSITION PHARMACEUTIQUE BLOQUANT LE SYSTÈME UBIQUITINE-PROTÉASOME DANS DES MALADIES
  申请人：UNIV TAIPEI MEDICAL

  公开号：WO2017014788A1

  公开（公告）日：2017-01-26

  The invention relates to new compounds with low cytotoxicity for blocking the ubiquitination- proteasome system in diseases. Accordingly, these compounds can be used in treatment of disorders including, but not limited to, cancers, neurodegenerative diseases, inflammatory disorders, autoimmune disorders and metabolic disorders.

  这项发明涉及一种新的化合物，具有低细胞毒性，用于阻断疾病中的泛素化-蛋白酶体系统。因此，这些化合物可用于治疗包括但不限于癌症、神经退行性疾病、炎症性疾病、自身免疫性疾病和代谢性疾病在内的疾病。
• Exploring Homogeneous Conditions for Mild Buchwald–Hartwig Amination in Batch and Flow
  作者：Saeed K. Kashani、Jacob E. Jessiman、Stephen G. Newman

  DOI：10.1021/acs.oprd.0c00018

  日期：2020.10.16

  Cross-couplings are among the most frequently used reactions in complex molecule synthesis. However, the requirement of stoichiometric base can cause challenges. Harsh, insoluble inorganic bases can lead to poor tolerance of sensitive functional groups, scale-up issues, and difficult adaptation to continuous flow platforms. Herein, we describe the use of high throughput experimentation to identify a number of conditions that enable Buchwald-Hartwig reactions to be carried out using readily available ligands (e.g., XantPhos) with DBU as a soluble, functional-group-tolerant, homogeneous base. Application of this system to diverse aminations in batch and flow are demonstrated, as is the translation of this technique to performing continuous Mizoroki-Heck and Sonogashira coupling reactions.