N-(4-氯苯基)-2-甲基-丙酰胺 | 7160-05-6

• 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: N-(4-氯苯基)-2-甲基-丙酰胺
• 英文名称: N-(4-chlorophenyl)isobutyramide
• 英文别名: N-(4-chlorophenyl)-2-methylpropanamide
• CAS: 7160-05-6
• 化学式: C₁₀H₁₂ClNO
• mdl: MFCD00243833
• 分子量: 197.664
• InChiKey: GBPHKLAKBDBGGE-UHFFFAOYSA-N

物化性质

• 熔点：
  139 °C
• 沸点：
  347.1±25.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(4-氯苯基)-2-甲基-丙酰胺 在 dipotassium peroxodisulfate 、 palladium diacetate 作用下， 以 甲烷磺酸 、 三氟乙酸 为溶剂， 反应 3.0h， 以41%的产率得到N,N′-(5,5′-dichloro[1,1′-biphenyl]-2,2′-diyl)bis(2-methylpropanamide)
  参考文献：
  名称：

  钯（II）在室温下催化芳族芳烃邻-sp 2 C–H键的氧化均相和交叉偶联

  摘要：

  通过在催化性Pd（OAc）2和K 2 S 2 O 8作为氧化剂的存在下，通过对苯甲酸酯的芳基邻-sp 2 C-H键进行氧化偶联，成功地完成了2,2'-双苯胺的制备。在室温（25°C）下在MsOH / CF 3 CO 2 H（TFA）中溶解。在这些偶联反应中，被各种给电子或吸电子基团取代的苯甲酸酯的芳环是可容忍的。

  DOI：

  10.1021/acs.joc.8b00120
• 作为产物：
  描述：

  2-bromo-2-methyl-N-(p-chlorophenyl)propanamide 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(4-氯苯基)-2-甲基-丙酰胺
  参考文献：
  名称：

  Electrochemical determination of the pKa of weak acids in N,N-dimethylformamide

  摘要：

  The electroreduction of NH-protic alpha-bromo amides in DMF generates an enolate-type base which undergoes a fast proton transfer from the parent compound (self-protonation), affording the corresponding reduced amide together with the conjugate base of the bromo amide. When an acid weaker than the bromo amide is added to the solution, a current increase in a potential region more negative than the main voltammetric reduction peak is observed under suitable conditions. The voltammetric pattern is in agreement with an unfavored protonation of the conjugate base of the starting compound by the added proton donor with regeneration of the electroactive bromo amide. The theoretical analysis of this reduction sequence has been carried out, and the voltammetric profiles have been simulated. Comparison of the experimental and simulated voltammetries led to the determination of the acidity difference, DELTA-pK(a), between the a-bromo amide and the added acid. For each alpha-bromo amide it was possible to obtain DELTA-pK(a) data ranging from 1.4 to 4.2. The use of a-bromo amides of different acidity with the same exogenous acids provided the link between the different sets of relative acidities. In this way, using six alpha-bromo amides, a relative acidity scale encompassing an overall pK(a) variation in DMF of about 10 units could be established. The relative scale was then anchored to the low pK(a) scale in DMF through both the determination of the acidity of selected acids and using a correlation between literature pK(a) data obtained in both DMF and DMSO. The application of this original electrochemical mechanism provided absolute pK(a) data in DMF ranging from about 16 to 26, i.e., a pK(a) region that is practically unexplored in this solvent.

  DOI：

  10.1021/ja00024a041

文献信息

• Reductive Acylation of Nitroarenes to Anilides by Sodium Sulfite in Carboxylic Acids
  作者：Mohammad Ghaffarzadeh、Pegah Akhavan

  DOI：10.1246/cl.140454

  日期：2014.9.5

  A facile and efficient reductive acylation of aromatic nitro compounds to corresponding anilides using a sodium sulfite–carboxylic acid system for the first time has been reported. The sodium sulfi...

  首次报道了使用亚硫酸钠-羧酸体系将芳香族硝基化合物轻松有效地还原酰化为相应的苯胺。硫化钠...
• Direct Hydrogenation of Nitroaromatics and One-Pot Amidation with Carboxylic Acids over Platinum Nanowires
  作者：Min Li、Lei Hu、Xueqin Cao、Haiyan Hong、Jianmei Lu、Hongwei Gu

  DOI：10.1002/chem.201002801

  日期：2011.2.25

  activity in various solvents under mild conditions and showed excellent stability. The catalytic performance was also evaluated in the one‐pot reduction of nitroaromatics and amidation with carboxylic acids under a hydrogen atmosphere at 100 °C. These methods for the hydrogenation of nitroaromatics and the direct amidation of nitroaromatics with carboxylic acids are simple, economical, and environmentally

  通过在甲醇中对FePt纳米线进行酸刻蚀，合成了长度均匀，直径为1.5 nm的新型超薄铂纳米线。这种纳米线的特征在于高分辨率透射电子显微镜（HRTEM）。X射线衍射（XRD）数据表明主平面为（111）。已经研究了该纳米线催化硝基芳族化合物的非均相氢化以给出相应的胺的能力。在温和的条件下，该催化剂在各种溶剂中显示出令人满意的活性，并显示出优异的稳定性。还通过在100°C的氢气气氛下一锅还原硝基芳烃和羧酸酰胺化来评估催化性能。
• A one pot protocol to convert nitro-arenes into <i>N</i>-aryl amides
  作者：Elisabetta Massolo、Margherita Pirola、Alessandra Puglisi、Sergio Rossi、Maurizio Benaglia

  DOI：10.1039/c9ra10758d

  日期：——

  one pot, experimentally simple protocol, based on readily available and inexpensive reagents allowed the conversion of nitro-arenes directly to N-aryl amides. A metal-free reduction of the nitro group, mediated by trichlorosilane, followed by the addition of an anhydride afforded the corresponding N-aryl carboxyamide, that was isolated after a simple aqueous work up in good-excellent yields. When the

  基于容易获得且廉价的试剂的两步一锅、实验简单的方案允许将硝基芳烃直接转化为N-芳基酰胺。由三氯硅烷介导的硝基的无金属还原，然后添加酸酐，得到相应的N-芳基羧酰胺，在简单的水处理后以良好的产率分离。当该方法应用于与γ-丁内酯的反应时，获得了所需的N-芳基丁酰胺衍生物，其特征在于γ位上有一个氯原子，这是一个功能化的手柄，可用于进一步合成操作反应产物。这种中间体已被用作药物活性化合物的关键先进前体。
• ARYL DIHYDROPYRIDINONE AND PIPERIDINONE MGAT2 INHIBITORS
  申请人：Bristol-Myers Squibb Company

  公开号：US20130143843A1

  公开（公告）日：2013-06-06

  The present invention provides compounds of Formula (I): or a stereoisomer, or a pharmaceutically acceptable salt thereof, wherein all of the variables are as defined herein. These compounds are monoacylglycerol acyltransferase type 2 (MGAT2) inhibitors which may be used as medicaments.

  本发明提供了以下式（I）的化合物： 或其立体异构体，或其药学上可接受的盐，其中所有变量如本文所定义。这些化合物是单酰基甘油酰基转移酶2（MGAT2）抑制剂，可用作药物。
• COMPOUNDS THAT INHIBIT HIF-1 ACTIVITY, THE METHOD FOR PREPARATION THEREOF AND THE PHARMACEUTICAL COMPOSITION CONTAINING THEM AS AN EFFECTIVE COMPONENT
  申请人：Lee Jung Joon

  公开号：US20090306078A1

  公开（公告）日：2009-12-10

  Disclosed herein are an HIF-1 inhibitor, a method for the preparation thereof, and a pharmaceutical composition comprising the same as an active ingredient. The HIF-1 inhibitor shows anticancer activity thanks to the inhibition activity against HIF-1, a transcription factor which plays an important role in the growth and metastasis of cancer, but not to general cytotoxicity. Thus, the HIF-inhibitor and a pharmaceutically acceptable salt thereof can be used as a therapeutic for various cancers such as liver cancer; stomach cancer and breast cancer. Also, the compound having inhibition activity against HIF-1 is useful in the treatment of diabetic retinopathy and arthritis, which are aggravated by HIF-1-mediated VEGF expression.

  本文披露了一种HIF-1抑制剂，其制备方法，以及包含其作为活性成分的药物组合物。该HIF-1抑制剂显示抗癌活性，这归功于其对HIF-1的抑制活性，HIF-1是一种在癌症生长和转移中起重要作用的转录因子，但不具有一般细胞毒性。因此，HIF抑制剂及其药用可接受的盐可用作治疗各种癌症，如肝癌、胃癌和乳腺癌的治疗药物。此外，具有对HIF-1抑制活性的化合物在治疗由HIF-1介导的VEGF表达加重的糖尿病视网膜病变和关节炎方面是有用的。