2-(thiophen-2-yl)-N-(p-tolyl)acetamide

• 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: 2-(thiophen-2-yl)-N-(p-tolyl)acetamide
• 英文别名: N-(4-methylphenyl)-2-(2-thienyl)acetamide；N-(4-methylphenyl)-2-thiophen-2-ylacetamide
• 化学式: C₁₃H₁₃NOS
• mdl: MFCD00458495
• 分子量: 231.318
• InChiKey: VLZJPOQVUSSPIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  57.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  噻酚-2-乙酰胺 、 对苄基三氟甲磺酸 在 tris-(dibenzylideneacetone)dipalladium(0) 、 C₃₆H₅₃O₃P 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium t-butanolate 作用下， 反应 4.0h， 以83%的产率得到2-(thiophen-2-yl)-N-(p-tolyl)acetamide
  参考文献：
  名称：

  联芳基膦氧烷配体促进的钯催化交叉偶联反应

  摘要：

  我们报告使用联芳基膦酸酯作为钯催化的交叉偶联反应的配体。开发了一种模块化合成方法，该方法采用将伯联芳基膦双共轭加成到1,1,5,5-四烷基五-1,4-二烯-3-酮中。值得注意的是，该合成不需要使用铜，铜是结构相关的联芳基膦配体中的已知污染物。使用上述合成策略，我们合成了联芳基膦酸酯的文库，改变了它们对磷的取代以及联芳基序的空间和电子性质。然后，我们在可溶有机碱存在下，将它们作为Pd催化的交叉偶联反应（如芳基磺酰胺化，芳基烷氧基化和芳基胺化）中的配体性能进行基准测试。在研究的每个反应中，许多配体的性能优于已知可促进给定转化的联芳基膦。使用高通量筛选技术确定了详细的底物范围。几种联芳基膦酸酯及其相应的Pd（II）氧化加成络合物已使用NMR光谱学和X射线晶体学进行了广泛表征。一般观察结果表明，联芳基膦酸酯可促进还原消除并与钯形成牢固的催化剂。在许多情况下，就较低的催化剂负载量，较短的反应时间和耐

  DOI：

  10.1021/acscatal.9b03012

文献信息

• Palladium Catalyzed Aminocarbonylation of Benzylic Ammonium Triflates with Nitroarenes: Synthesis of Phenylacetamides
  作者：Li‐Miao Yang、Shan‐Shan Li、You‐Ya Zhang、Jin‐Liang Lu、Jing‐Tong Deng、Ai‐Jun Ma、Xiang‐Zhi Zhang、Shu‐Yu Zhang、Jin‐Bao Peng

  DOI：10.1002/adsc.202001561

  日期：2021.4.13

  A palladium catalyzed reductive aminocarbonylation of benzylic ammonium triflates with nitroarenes for the synthesis of phenylacetamides was developed. Using Pd(acac)2/DPPF catalyst system, a range of different substituted phenylacetamides were prepared in moderate to good yields from benzylic ammonium triflates and nitroarenes through Csp3−N bond cleavage. A variety of alkyl, aryl, and halide substituents

  开发了钯催化的苄基三氟甲磺酸铵与硝基芳烃的还原性氨基羰基化反应，用于合成苯乙酰胺。使用Pd（acac）2 / DPPF催化剂体系，通过Csp 3 -N键裂解，从苄基三氟甲磺酸铵和硝基芳烃以中等到良好的产率制备了一系列不同的取代苯基乙酰胺。可以在两个底物上使用多种烷基，芳基和卤化物取代基，并且可以容许许多有用的官能团。
• Synthesis and biological evaluation of N-(aryl)-2-thiophen-2-ylacetamides series as a new class of antitubercular agents
  作者：Maria Cristina Silva Lourenço、Felipe Rodrigues Vicente、Maria das Graças Muller de Oliveira Henriques、André Luis Peixoto Candéa、Raoni Schroeder Borges Gonçalves、Thais Cristina M. Nogueira、Marcelle de Lima Ferreira、Marcus Vinícius Nora de Souza

  DOI：10.1016/j.bmcl.2007.09.096

  日期：2007.12

  The present article describes a series of 21 N-(aryl)-2-thiophen-2-ylacetamides, which were synthesized and evaluated for their in vitro antibacterial activity against Mycobacterium tuberculosis, and the activity expressed as the minimum inhibitory concentration (MIC) in mu g/mL. The compounds 2, 3, 7, 8,11, 12, 15,16, and 20 exhibited activity between 25 and 100 mu g/mL and could be a good start point to find new lead compounds in the fight against multidrug resistant tuberculosis. (c) 2007 Elsevier Ltd. All rights reserved.
• [EN] SMALL MOLECULE INHIBITORS OF ONCOGENIC CHD1L WITH PRECLINICAL ACTIVITY AGAINST COLORECTAL CANCER<br/>[FR] INHIBITEURS À PETITES MOLÉCULES DE CHD1L ONCOGÈNES PRÉSENTANT UNE ACTIVITÉ PRÉCLINIQUE CONTRE LE CANCER COLORECTAL
  申请人：UNIV COLORADO REGENTS

  公开号：WO2021195279A2

  公开（公告）日：2021-09-30

  Treatment of CHD1L-driven cancers, including TCF transcription-driven cancers and EMT-driven cancers using CHD1L inhibitors. Small molecule inhibitors of CHDL1 which inhibit CHD1L ATPase and inhibit CHD1L-dependent TCF-transcription have been identified. CHD1L inhibitors prevent the TCF-complex from binding to Wnt response elements and promoter sites. More specifically, CHD1L inhibitors induce the reversion of EMT. CHD1L inhibitors are useful in the treatment of various cancers and particularly CRC and m-CRC. The CHD1L-driven cancer is among others, CRC, breast cancer, glioma, liver cancer, lung cancer or gastrointestinal (GI) cancers. CHD1L inhibitors of formulas I and XX and salts thereof as defined herein are provided as well as pharmaceutical compositions containing CHD1L inhibitors. Synergistic combinations of CHD1L inhibitors with other antineoplastic agents are also described.