methyl 3-(4-chlorophenyl)thiophene-2-carboxylate | 22099-15-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: methyl 3-(4-chlorophenyl)thiophene-2-carboxylate
• 英文别名: 3-(4-chloro-phenyl)-thiophene-2-carboxylic acid methyl ester
• CAS: 22099-15-6
• 化学式: C₁₂H₉ClO₂S
• 分子量: 252.721
• InChiKey: WRNYEINWQFJNJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氨基-2-噻吩甲酸甲酯 在 potassium phosphate 、 四(三苯基膦)钯 、 亚硝酸特丁酯 、 copper(ll) bromide 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 6.0h， 生成 methyl 3-(4-chlorophenyl)thiophene-2-carboxylate
  参考文献：
  名称：

  Design and synthesis of condensed thienocoumarins by Suzuki–Miyaura reaction/lactonization tandem protocol

  摘要：

  A concise and efficient approach to a series of chromen-4-ones with fused thiophene ring has been developed using the Suzuki-Miyaura reaction of bromothiophene-2- and 3-carboxylates with 2-methoxyboronic acids and subsequent cyclization of prepared alkyl (2-methoxy)aryl thiophene-2- and 3-carboxylates under the action of BBr3/KOtBu. Starting bromothiophenes are easily obtained from corresponding commercially available aminothiophenes by diazotization/bromination reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.096

文献信息

• Visible-Light-Promoted, Catalyst-Free Gomberg–Bachmann Reaction: Synthesis of Biaryls
  作者：Juyoung Lee、Boseok Hong、Anna Lee

  DOI：10.1021/acs.joc.9b00557

  日期：2019.7.19

  Biaryls were synthesized via a novel visible-light-promoted Gomberg–Bachmann reaction that does not require a photosensitizer or any metal reagents. The formation of an electron donor–acceptor complex between aryl diazonium salts and pyridine allows, under visible-light irradiation, the synthesis of biaryls in moderate-to-high yields.

  联芳基是通过不需要光敏剂或任何金属试剂的新型可见光促进的Gomberg-Bachmann反应合成的。在芳基重氮盐和吡啶之间形成电子供体-受体配合物，可以在可见光照射下以中等至高收率合成联芳基。
• Gold catalysed Suzuki-Miyaura coupling of arenediazonium o-benzenedisulfonimides
  作者：Margherita Barbero、Stefano Dughera

  DOI：10.1016/j.tet.2018.08.018

  日期：2018.9

  Arenediazonium o-benzenedisulfonimides have been used as efficient electrophilic partners in Au(I) catalysed Suzuki coupling reactions. The synthetic protocol is general, easy and produced either biaryls or heteroaryl arenes in good yields (51 positive examples, average yield 80%). o-Benzenedisulfonimide was recovered at the end of the reactions and was reused to prepare the starting salts for further

  Arenediazonzon邻苯二磺酰亚胺已被用作Au（I）催化的Suzuki偶联反应中的有效亲电子伙伴。合成规程是通用的，容易的并且以高收率生产联芳基或杂芳基芳烃（51个阳性实例，平均收率80％）。在反应结束时回收邻苯二甲磺酰亚胺，并重新用于制备起始盐以用于进一步的反应。机械学的见解表明，邻苯二磺酰亚胺阴离子起电子转移剂的作用，并促进了不需要光催化剂或外部氧化剂存在的催化循环。
• Design and synthesis of condensed thienocoumarins by Suzuki–Miyaura reaction/lactonization tandem protocol
  作者：Viktor O. Iaroshenko、Sajid Ali、Satenik Mkrtchyan、Ashot Gevorgyan、Tariq Mahmood Babar、Volodymyr Semeniuchenko、Zahid Hassan、Alexander Villinger、Peter Langer

  DOI：10.1016/j.tetlet.2012.10.096

  日期：2012.12

  A concise and efficient approach to a series of chromen-4-ones with fused thiophene ring has been developed using the Suzuki-Miyaura reaction of bromothiophene-2- and 3-carboxylates with 2-methoxyboronic acids and subsequent cyclization of prepared alkyl (2-methoxy)aryl thiophene-2- and 3-carboxylates under the action of BBr3/KOtBu. Starting bromothiophenes are easily obtained from corresponding commercially available aminothiophenes by diazotization/bromination reaction. (C) 2012 Elsevier Ltd. All rights reserved.