diethyl benzo[b]thiophene-2,3-dicarboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: diethyl benzo[b]thiophene-2,3-dicarboxylate
• 英文别名: Diethyl 1-benzothiophene-2,3-dicarboxylate
• 化学式: C₁₄H₁₄O₄S
• 分子量: 278.329
• InChiKey: SBWDYLAMIGCDBL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  80.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  benzo[b]thiophene-2,3-dicarboxylic acid 生成 diethyl benzo[b]thiophene-2,3-dicarboxylate
  参考文献：
  名称：

  Mayer, Justus Liebigs Annalen der Chemie, 1931, vol. 488, p. 259,275

  摘要：

  DOI：

文献信息

• Facile Access to Benzothiophenes through Metal-Free Iodine-­Catalyzed Intermolecular Cyclization of Thiophenols and Alkynes
  作者：Daoshan Yang、Hua Wang、Kelu Yan、Mengqi Zhang、Wei Wei、Yao Liu、Laijin Tian

  DOI：10.1055/s-0034-1378841

  日期：——

  A novel iodine-catalyzed method for the synthesis of benzothiophene derivatives through cascade reactions of substituted thiophenols with alkynes has been demonstrated under metal- and solvent-free conditions. The present protocol uses inexpensive and environmentally friendly molecular iodine as the catalyst, and the corresponding products are obtained in moderate to excellent yields. Such an efficient

  在无金属和无溶剂条件下，证明了一种通过取代苯硫酚与炔烃的级联反应合成苯并噻吩衍生物的新型碘催化方法。本协议使用廉价且环保的分子碘作为催化剂, 并以中等至优良的收率获得相应的产品。这种高效、经济和绿色的转化应该为有机和药物化学中的各种苯并噻吩提供一种有吸引力的方法。
• A practical synthesis of benzothiophenes via visible-light-promoted cyclization of disulfides and alkynes
  作者：Lin-Miao Ye、Lu Qian、Yan-Yan Chen、Xue-Jing Zhang、Ming Yan

  DOI：10.1039/c6ob02461k

  日期：——

  Visible-light-promoted radical cyclization of disulfides and alkynes provided benzothiophenes in good yields.

  可见光促进的二硫化物和炔烃的自由基环化反应可以高产得苯并噻吩。
• σ-Bond initiated generation of aryl radicals from aryl diazonium salts
  作者：Elene Tatunashvili、Bun Chan、Philippe E. Nashar、Christopher S. P. McErlean

  DOI：10.1039/d0ob00205d

  日期：——

  transform aryl diazonium salts into aryl radicals. Experimental and computational studies show that Hantzsch esters transfer hydride to aryl diazonium species, and that oxygen initiates radical fragmentation of the diazene intermediate to produce aryl radicals. The operational simplicity of this addition-fragmentation process for the generation of aryl radicals, by a polar-radical crossover mechanism, has been

  σ键亲核试剂和分子氧将芳基重氮盐转化为芳基。实验和计算研究表明，汉茨酯将氢化物转移到芳基重氮化合物上，并且氧引发了重氮中间体的自由基断裂，从而产生了芳基。在各种形成键的反应中已经说明了这种加成-断裂过程通过极性自由基交换机理产生芳基的操作简便性。
• Metal-free n-Et₄NBr-catalyzed radical cyclization of disulfides and alkynes leading to benzothiophenes under mild conditions
  作者：Daoshan Yang、Kelu Yan、Wei Wei、Laijin Tian、Qinghe Li、Jinmao You、Hua Wang

  DOI：10.1039/c4ra08260e

  日期：——

  A novel n-Et4NBr-catalyzed method for the synthesis of benzothiophene derivatives via cascade reactions of substituted disulfides with alkynes through S–S bond cleavage and alkenyl radical cyclization reactions has been developed. The reaction has a high functional-group tolerance. The new method is environmental and practical, and the starting materials are readily available. These advantages, relative

  已开发出一种新颖的n - Et 4 NBr催化方法，该方法通过取代的二硫化物与炔烃的S–S键断裂和烯基自由基环化反应的级联反应合成苯并噻吩衍生物。该反应具有较高的官能团耐受性。该新方法是环境实用的，并且起始材料容易获得。相对于先前的方法，这些优点为构建各种有用的苯并噻吩基序提供了机会。
• Application of Pyridinium 1,4-Zwitterionic Thiolates: Synthesis of Benzopyridothiazepines and Benzothiophenes
  作者：Bin Cheng、Yuntong Li、Taimin Wang、Xinping Zhang、Hui Li、Yixuan He、Yun Li、Hongbin Zhai

  DOI：10.1021/acs.joc.0c00374

  日期：2020.5.15

  synthon, have been applied to the synthesis of 12aH-benzo[f]pyrido[1,2-d][1,4]thiazepines and benzo[b]thiophenes. Benzopyridothiazepines were produced through a 1,5-dipolar cycloaddition reaction from pyridinium 1,4-zwitterionic thiolates with arynes, whereas benzothiophenes as side products were generated via a [3 + 2] cascade cyclization reaction. The [5 + 2] reaction mode of pyridinium 1,4-zwitterionic

  1,4-两性离子硫醇吡啶鎓是一种新​​型的含硫合成子，已被用于合成12aH-苯并[f]吡啶基[1,2-d] [1,4]噻嗪和苯并[b]噻吩。苯并吡啶并硫氮杂s是由1,4-两性离子硫醇吡啶鎓与芳烃通过1,5-偶极环加成反应生成的，而副产物苯并噻吩是通过[3 + 2]级联环化反应生成的。吡啶鎓1，4-两性离子硫醇盐的[5 + 2]反应模式是首次公开。