3-methoxy-2,3'-bithiophene

• 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: 3-methoxy-2,3'-bithiophene
• 英文别名: 3-Methoxy-2-thiophen-3-ylthiophene；3-methoxy-2-thiophen-3-ylthiophene
• 化学式: C₉H₈OS₂
• 分子量: 196.294
• InChiKey: WTZLACWMWYEBCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-methoxy-2,3'-bithiophene 、 二氯苯酚溴酯 在 四丁基碘化铵 、 三乙胺 作用下， 以 氯苯 为溶剂， 反应 24.0h， 以95%的产率得到5-phenyl-5H-dithieno[2,3-c:2',3'-e][1,2]oxaborinine
  参考文献：
  名称：

  Iodide-Mediated or Iodide-Catalyzed Demethylation and Friedel–Crafts C–H Borylative Cyclization Leading to Thiophene-Fused 1,2-Oxaborine Derivatives

  摘要：

  The first synthesis of dithieno-1,2-oxaborine derivatives was achieved via iodide-mediated or iodide-catalyzed demethylation of 3-methoxy-2,2'-bithiophene and subsequent C-H borylation. A wide variety of thiophene-fused oxaborines could be synthesized by the procedure.

  DOI：

  10.1021/acs.orglett.9b00485
• 作为产物：
  描述：

  3-甲氧基噻吩 在 三氟甲磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以91%的产率得到3-methoxy-2,3'-bithiophene
  参考文献：
  名称：

  亲核本位通过芳基C-OME键裂解芳基甲基醚的3'-取代; 获得功能化的双噻吩

  摘要：

  已经描述了通过芳基C–OMe键的直接亲核取代来实现芳基甲基醚官能化的无金属和无溶剂策略。已经成功地采用了各种以O，S，N和C为中心的不带电亲核试剂。使用该协议，已经以简单的方式合成了双噻吩的功能性衍生物。该反应是高度原子效率的，并且产生甲醇作为唯一的副产物。

  DOI：

  10.1021/acs.joc.6b02701

文献信息

• Direct C−H Arylation of (Hetero)arenes with Aryl Iodides via Rhodium Catalysis
  作者：Shuichi Yanagisawa、Tomoko Sudo、Ryoji Noyori、Kenichiro Itami

  DOI：10.1021/ja064500p

  日期：2006.9.1

  A new method for the catalytic C-H arylation of heteroarenes and arenes that manifests high activity paired with reasonably broad scope was developed. Under the catalytic influence of RhCl(CO)P[OCH(CF3)2]3}2 and Ag2CO3, the direct C-H arylation of heteroarenes/arenes with aryl/heteroaryl iodides took place to afford a range of biaryls in good to excellent yields with high regioselectivity. Thiophenes, furans, pyrroles, indoles, and alkoxybenzenes are applicable in this arylation protocol.
• Direct coupling of arenes and iodoarenes catalyzed by a rhodium complex with a strongly π-accepting phosphite ligand
  作者：Shuichi Yanagisawa、Tomoko Sudo、Ryoji Noyori、Kenichiro Itami

  DOI：10.1016/j.tet.2008.01.053

  日期：2008.6

  A new rhodium-based catalytic system for the direct C-H coupling of arenes and iodoarenes that shows high activity with reasonably broad scope was developed. Under the catalytic influence of RhCl(CO)P[OCH(CF3)(2)](3)}(2) and Ag2CO3, the direct C-H arylation of heteroarenes and arenes took place with iodoarenes to afford a range of biaryls in good to excellent yields with high regioselectivity. Thiophenes, furans, pyrroles, indoles, and alkoxybenzenes are applicable to this arylation protocol. (C) 2008 Elsevier Ltd. All rights reserved.
• Iodide-Mediated or Iodide-Catalyzed Demethylation and Friedel–Crafts C–H Borylative Cyclization Leading to Thiophene-Fused 1,2-Oxaborine Derivatives
  作者：Keisuke Shigemori、Momoka Watanabe、Julie Kong、Koichi Mitsudo、Atsushi Wakamiya、Hiroki Mandai、Seiji Suga

  DOI：10.1021/acs.orglett.9b00485

  日期：2019.4.5

  The first synthesis of dithieno-1,2-oxaborine derivatives was achieved via iodide-mediated or iodide-catalyzed demethylation of 3-methoxy-2,2'-bithiophene and subsequent C-H borylation. A wide variety of thiophene-fused oxaborines could be synthesized by the procedure.
• Nucleophilic <i>ipso</i>-Substitution of Aryl Methyl Ethers through Aryl C–OMe Bond Cleavage; Access to Functionalized Bisthiophenes
  作者：Abhishek Kumar Mishra、Ajay Verma、Srijit Biswas

  DOI：10.1021/acs.joc.6b02701

  日期：2017.4.7

  A metal and solvent free strategy to functionalize aryl methyl ethers through direct nucleophilic substitution of aryl C–OMe bond has been described. A wide range of O, S, N, and C-centered uncharged nucleophiles has been successfully employed. Using this protocol, functional derivatives of bisthiophene have been synthesized in a straightforward way. The reactions are highly atom-efficient and generate

  已经描述了通过芳基C–OMe键的直接亲核取代来实现芳基甲基醚官能化的无金属和无溶剂策略。已经成功地采用了各种以O，S，N和C为中心的不带电亲核试剂。使用该协议，已经以简单的方式合成了双噻吩的功能性衍生物。该反应是高度原子效率的，并且产生甲醇作为唯一的副产物。