dimethyl 5-methoxybenzo[b]thiophene-2,3-dicarboxylate | 1429655-24-2

• 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: dimethyl 5-methoxybenzo[b]thiophene-2,3-dicarboxylate
• 英文别名: Dimethyl 5-methoxy-1-benzothiophene-2,3-dicarboxylate；dimethyl 5-methoxy-1-benzothiophene-2,3-dicarboxylate
• CAS: 1429655-24-2
• 化学式: C₁₃H₁₂O₅S
• 分子量: 280.301
• InChiKey: MKNKXTXAMPGRII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  90.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4,4'-二甲氧基二苯二硫 、 丁炔二酸二甲酯 在 dipotassium peroxodisulfate 、 四乙基溴化铵 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以85%的产率得到dimethyl 5-methoxybenzo[b]thiophene-2,3-dicarboxylate
  参考文献：
  名称：

  在温和条件下， 无金属的n -Et 4 NBr催化的二硫化物和炔烃自由基环化反应生成苯并噻吩†

  摘要：

  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。

  DOI：

  10.1039/c4ra08260e

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。
• Air promoted annulation of thiophenols with alkynes leading to benzothiophenes
  作者：Yajun Wang、Rui Wu、Shijun Zhao、Zhengjun Quan、Yingpeng Su、Congde Huo

  DOI：10.1039/c8ob00010g

  日期：——

  Air promoted intermolecular annulation of thiophenols with alkynes, leading to complex benzothiophenes, is reported.

  空气促进了硫酚与炔烃的分子间环化反应，形成复杂的苯并噻吩化合物。
• Visible-light-induced synthesis of benzothiophenes and benzoselenophenes via the annulation of thiophenols or 1,2-diphenyldiselane with alkynes
  作者：Xiao-Feng Xia、Guo-Wei Zhang、Su-Li Zhu

  DOI：10.1016/j.tet.2017.03.053

  日期：2017.5

  An effective metal-free photoredox-mediated tandem addition/cyclization reaction of thiophenols or 1,2-diphenyldiselane with alkynes leads to 2,3-disubstituted benzothiophenes and benzoselenophenes. Blue light irradiation of the organic dye, Mes-Acr-Me+, initiates the photoredox catalysis. A series of functional groups could be tolerated under ambient conditions, and good to excellent yields were generated. (C) 2017 Elsevier Ltd. All rights reserved.
• Direct Benzothiophene Formation via Oxygen-Triggered Intermolecular Cyclization of Thiophenols and Alkynes Assisted by Manganese/PhCOOH
  作者：Kaisheng Liu、Fan Jia、Hui Xi、Yuanming Li、Xiaojian Zheng、Qiaoxia Guo、Baojian Shen、Zhiping Li

  DOI：10.1021/ol400719d

  日期：2013.4.19

  An intermolecular oxidative cyclization between thiophenols and alkynes for benzothiophene formation has been established. A variety of multifunctional benzothiophenes are synthesized. In addition, we demonstrated that the obtained benzothiophenes can be used for further transformation to give diverse benzothiophene derivatives efficiently and selectively.