3-苯甲酰胺基噻吩 | 79128-75-9

• 物质功能分类: 医药中间体 - 噻吩类化合物
• 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: 3-苯甲酰胺基噻吩
• 英文名称: N-Thiophen-3-yl-benzamide
• 英文别名: n-(Thiophen-3-yl)benzamide；N-thiophen-3-ylbenzamide
• CAS: 79128-75-9
• 化学式: C₁₁H₉NOS
• 分子量: 203.265
• InChiKey: ZEGOLEIUSWHEOZ-UHFFFAOYSA-N

物化性质

• 熔点：
  153 °C
• 沸点：
  250.9±13.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 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：
  57.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-苯甲酰胺基噻吩 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以82%的产率得到N-benzylthiophen-3-amine
  参考文献：
  名称：

  Outurquin, Francis; Lerouge, Patrice; Paulmier, Claude, Bulletin de la Societe Chimique de France, 1986, # 2, p. 259 - 266

  摘要：

  DOI：
• 作为产物：
  描述：

  3-硝基噻吩 在 盐酸 、 tin 作用下， 生成 3-苯甲酰胺基噻吩
  参考文献：
  名称：

  Steinkopf; Hoepner, Justus Liebigs Annalen der Chemie, 1933, vol. 501, p. 174,182

  摘要：

  DOI：

文献信息

• Nanoparticle mediated organic synthesis (NAMO-synthesis): CuI-NP catalyzed ligand free amidation of aryl halides
  作者：Atul Kumar、Ajay Kumar Bishnoi

  DOI：10.1039/c4ra06804a

  日期：——

  The first CuI-nanoparticle catalyzed ligand free synthesis of N-aryl amides from aryl halides and arylamides/cyclic amides has been developed. This methodology is further extended for the synthesis of nitrogen heterocycles such as benzimidazole, and quinazolinone via intermolecular amidation reaction followed by cyclization. TEM images of the CuI-NP catalyst showed spherical, well-dispersed particles

  已经开发了由CuI-纳米颗粒催化的从芳基卤化物和芳基酰胺/环状酰胺的N-芳基酰胺的无配体的合成。该方法进一步扩展用于通过分子间酰胺化反应然后环化来合成氮杂环，例如苯并咪唑和喹唑啉酮。CuI-NP催化剂的TEM图像显示球形，分散良好的颗粒，为反应性提供了较大的表面积，并具有良好的可回收性。
• Efficient and Mild Ullmann-Type N-Arylation of Amides, Carbamates, and Azoles in Water
  作者：Maud Bollenbach、Pedro G. V. Aquino、João Xavier de Araújo-Júnior、Jean-Jacques Bourguignon、Frédéric Bihel、Christophe Salomé、Patrick Wagner、Martine Schmitt

  DOI：10.1002/chem.201700832

  日期：2017.10.4

  A simple, sustainable, efficient, mild, and low‐cost protocol was developed for d‐glucose‐assisted Cu‐catalyzed Ullmann reactions in water for amides, carbamates, and nitrogen‐containing heterocycles. The reaction was compatible with diverse aryl/heteroaryl iodides, giving highly substituted pyridine, indole, or indazole rings. This method offers an attractive alternative to existing protocols, because

  开发了一种简单，可持续，高效，温和且低成本的方案，用于葡萄糖在水中的酰胺，氨基甲酸酯和含氮杂环的d葡萄糖辅助的Ullmann反应。该反应与各种芳基/杂芳基碘化物相容，得到高度取代的吡啶，吲哚或吲唑环。该方法为现有方案提供了一种有吸引力的替代方法，因为该反应在水性介质中进行，在环境温度或接近环境温度的条件下进行，并提供高收率或高收率的N-芳基化产物。
• Copper-catalyzed formation of carbon-heteroatom and carbon-carbon bonds
  申请人：——

  公开号：US20030065187A1

  公开（公告）日：2003-04-03

  The present invention relates to copper-catalyzed carbon-heteroatom and carbon-carbon bond-forming methods. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of an amide or amine moiety and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In additional embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between a nitrogen atom of an acyl hydrazine and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In other embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-nitrogen bond between the nitrogen atom of a nitrogen-containing heteroaromatic, e.g., indole, pyrazole, and indazole, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. In certain embodiments, the present invention relates to copper-catalyzed methods of forming a carbon-oxygen bond between the oxygen atom of an alcohol and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. The present invention also relates to copper-catalyzed methods of forming a carbon-carbon bond between a reactant comprising a nucleophilic carbon atom, e.g., an enolate or malonate anion, and the activated carbon of an aryl, heteroaryl, or vinyl halide or sulfonate. Importantly, all the methods of the present invention are relatively inexpensive to practice due to the low cost of the copper comprised by the catalysts.

  本发明涉及铜催化的碳-杂原子和碳-碳键形成方法。在某些实施例中，本发明涉及铜催化的方法，用于在酰胺或胺基团的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在其他实施例中，本发明涉及铜催化的方法，用于在酰基肼的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在另一些实施例中，本发明涉及铜催化的方法，用于在含氮杂环芳烃（例如吲哚、吡唑和吲哌）的氮原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氮键。在某些实施例中，本发明涉及铜催化的方法，用于在醇的氧原子与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-氧键。本发明还涉及铜催化的方法，用于在包含亲核碳原子的反应物（例如烯醇酸盐或丙二酸盐负离子）与芳基、杂原基或乙烯卤代物或磺酸酯的活化碳之间形成碳-碳键。重要的是，由于催化剂中铜的低成本，本发明的所有方法都相对廉价。
• Rhodium-catalyzed Electrophilic Amination of Arylboronic Acids with Secondary Hydroxylamines
  作者：Tomohiro Yasuhisa、Koji Hirano、Masahiro Miura

  DOI：10.1246/cl.161158

  日期：2017.4.5

  A rhodium(III)-catalyzed electrophilic amination of arylboronic acids with secondary hydroxylamines has been developed. The rhodium catalysis is compatible with heteroarylboronic acids as well as acyl and alkoxycarbonyl protecting groups on the nitrogen of O-acylhydroxylamines, and the corresponding secondary anilines are obtained in good to excellent yields.

  已经开发了铑 (III) 催化的芳基硼酸与仲羟胺的亲电胺化。铑催化与杂芳基硼酸以及O-酰基羟胺的氮上的酰基和烷氧羰基保护基团相容，并且以良好到优异的产率获得相应的仲苯胺。
• Switching from Biaryl Formation to Amidation with Convoluted Polymeric Nickel Catalysis
  作者：Abhijit Sen、Raghu N. Dhital、Takuma Sato、Aya Ohno、Yoichi M. A. Yamada

  DOI：10.1021/acscatal.0c03888

  日期：2020.12

  and we confirmed that it is consistent with Ni K-edge EXAFS. The Suzuki–Miyaura-type coupling of aryl halides and arylboronic esters proceeded using P4VP-NiCl2 (0.1 mol % Ni) to give the corresponding biaryl compounds in up to 94% yield. Surprisingly, when the same reaction of aryl halides and arylboronic acid/ester was carried out in the presence of amides, the amidation proceeded predominantly to

  通过聚（4-乙烯基吡啶）（P4VP）和氯化镍的分子卷积制备了稳定，可重复使用且不溶的聚（4-乙烯基吡啶）镍催化剂（P4VP-NiCl 2）。我们基于元素分析和Ni K-edge XANES提出了前催化剂中Ni中心的配位结构，并证实它与Ni K-edge EXAFS一致。使用P4VP-NiCl 2进行芳基卤化物和芳基硼​​酸酯的Suzuki-Miyaura型偶联（0.1mol％Ni）得到相应的联芳基化合物，产率高达94％。出人意料的是，当在酰胺存在下进行芳基卤化物和芳基硼​​酸/酯的相同反应时，酰胺化主要进行，从而以高达99％的产率得到相应的芳基酰胺。相反，在不存在芳基硼酸/酯的情况下，芳基卤化物和酰胺的反应没有进行。P4VP-NiCl 2成功地催化了内酰胺化反应，制备了菲啶酮。P4VP-NiCl 2被重复使用了五次，而催化活性没有明显损失。使用P4VP-NiCl 2有效合成药物，天然产物和