methyl [2,3'-bithiophene]-2'-carboxylate | 128402-32-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: methyl [2,3'-bithiophene]-2'-carboxylate
• 英文别名: Methyl 3-thiophen-2-ylthiophene-2-carboxylate
• CAS: 128402-32-4
• 化学式: C₁₀H₈O₂S₂
• 分子量: 224.304
• InChiKey: MNMWQGPCHIBJIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  82.8
• 氢给体数：
  0
• 氢受体数：
  4

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 [2,3'-bithiophene]-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

• Metal-Free, Visible-Light-Mediated Direct C–H Arylation of Heteroarenes with Aryl Diazonium Salts
  作者：Durga Prasad Hari、Peter Schroll、Burkhard König

  DOI：10.1021/ja212099r

  日期：2012.2.15

  Visible light along with 1 mol % eosin Y catalyzes the direct C-H bond arylation of heteroarenes with aryl diazonium salts by a photoredox process. We have investigated the scope of the reaction for several aryl diazonium salts and heteroarenes. The general and easy procedure provides a transition-metal-free alternative for the formation of aryl-heteroaryl bonds.

  可见光和 1 mol% 曙红 Y 通过光氧化还原过程催化杂芳烃与芳基重氮盐的直接 CH 键芳基化。我们研究了几种芳基重氮盐和杂芳烃的反应范围。通用且简单的程序为芳基-杂芳基键的形成提供了一种不含过渡金属的替代方法。
• Redox reactions of small organic molecules using ball milling and piezoelectric materials
  作者：Koji Kubota、Yadong Pang、Akira Miura、Hajime Ito

  DOI：10.1126/science.aay8224

  日期：2019.12.20

  bond-forming reactions. We postulated that a complementary method for the redox-activation of small organic molecules in response to applied mechanical energy could be developed through the piezoelectric effect. Here, we report that agitation of piezoelectric materials via ball milling reduces aryl diazonium salts. This mechanoredox system can be applied to arylation and borylation reactions under mechanochemical

  球磨机中的氧化还原催化 在球磨机中混合固体反应物是避免与大多数化学合成相关的大量溶剂浪费的有前途的方法。久保田等人。现在报告说，在混合物中添加压电催化剂可以通过明显的电子转移循环促进键的形成（参见 Xia 和 Wang 的观点）。具体而言，钛酸钡以类似于液相光氧化还原催化的方式激活芳基重氮盐进行硼酸化并与杂环偶联。该反应对空气不敏感，并被证明达到克级。科学，这个问题 p。1500；另见第。1451 一种压电材料似乎作为电子转移催化剂在固态搅拌下激活芳基重氮盐。在过去的十年，光氧化还原催化利用光能来加速成键反应。我们假设可以通过压电效应开发一种补充方法，用于响应施加的机械能而氧化还原小有机分子。在这里，我们报告了通过球磨搅拌压电材料可以减少芳基重氮盐。该机械氧化还原系统可应用于机械化学条件下的芳基化和硼化反应。
• MECHANOREDOX REACTION USING PIEZOELECTRIC MATERIAL, AND PRODUCTION METHOD USING SAID REACTION
  申请人：NATIONAL UNIVERSITY CORPORATION HOKKAIDO UNIVERSITY

  公开号：US20220306654A1

  公开（公告）日：2022-09-29

  Disclosed are a method for producing a highly reactive intermediate, which comprises: preparing an electron-accepting active compound (1), preparing a piezoelectric material (3), and applying mechanical strain to the piezoelectric material (3) in the presence of the electron-accepting active compound (1) and the piezoelectric material (3), and subjecting the compound (1) to one-electron reduction to generate a corresponding highly reactive intermediate; a redox reaction method using the method for producing the same; and a method for producing a redox reaction product.

  揭示了一种制备高反应性中间体的方法，包括：制备一个电子受体活性化合物（1），制备一个压电材料（3），并在存在电子受体活性化合物（1）和压电材料（3）的情况下对压电材料（3）施加机械应变，并将化合物（1）进行单电子还原以生成相应的高反应性中间体；使用上述制备方法的氧化还原反应方法；以及一种制备氧化还原反应产物的方法。
• Visible light-driven C–H arylation of heteroarenes with aryl diazonium salts in water catalyzed by a Z-scheme CuInS2/K-C3N4 heterojunction
  作者：Qian-Hui Liu、Shi-Long Kang、Zhen-Shui Cui、Yu-Heng Liu、Mo Zhang、Zhan-Hui Zhang

  DOI：10.1039/d4gc00502c

  日期：——

  and synthesized. The structure and composition of CuInS2/K-C3N4 were well characterized. The arylation of heteroarenes with aryl diazonium salts driven by a heterogeneous CuInS2/K-C3N4 catalytic system was established under visible light irradiation in water for the first time. A variety of arylated heteroarenes were synthesized in high yields with commendable functional group tolerance. The designed

  设计并合成了CuInS 2量子点修饰的KC 3 N 4 Z型异质结。CuInS 2 /KC 3 N 4的结构和组成得到了很好的表征。首次在水中可见光照射下建立了多相CuInS 2 /KC 3 N 4催化体系驱动的杂芳烃与芳基重氮盐的芳基化反应。以高产率合成了多种芳基化杂芳烃，并具有值得称赞的官能团耐受性。设计的CuInS 2 /KC 3 N 4光催化剂可以多次回收和重复使用，而不会显着降低其催化活性。
• Hatanaka, Yasuo; Fukushima, Satoshi; Hiyama, Tamejiro, Heterocycles, 1990, vol. 30, # 1, p. 303 - 306
  作者：Hatanaka, Yasuo、Fukushima, Satoshi、Hiyama, Tamejiro

  DOI：——

  日期：——