2-(thiophen-3-yl)benzo[b]thiophene | 55164-49-3

• 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: 2-(thiophen-3-yl)benzo[b]thiophene
• 英文别名: 2-Thiophen-3-yl-1-benzothiophene
• CAS: 55164-49-3
• 化学式: C₁₂H₈S₂
• 分子量: 216.328
• InChiKey: ATJPJAGDNHOCQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-((2-bromophenyl)ethynyl)thiophene 在 tris-(dibenzylideneacetone)dipalladium(0) 、 四丁基氟化铵 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.03h， 生成 2-(thiophen-3-yl)benzo[b]thiophene
  参考文献：
  名称：

  实用的一锅法从溴代炔和邻炔烷基溴苯合成高度取代的噻吩和苯并[ b ]噻吩

  摘要：

  由容易获得的溴代炔和邻炔基溴苯衍生物已开发出噻吩和苯并[ b ]噻吩的有效合成方法。这种新颖的一锅法涉及使用硫化氢替代物进行钯催化的C–S键形成，然后进行杂环化反应。此外，用选定的亲电试剂进行原位官能化进一步扩大了该方法在制备相应的高度取代的硫杂环化合物方面的潜力。

  DOI：

  10.1021/ol201970m

文献信息

• Synthesis of 2-substituted benzo[<i>b</i>]thiophenes <i>via</i> gold(<scp>i</scp>)–NHC-catalyzed cyclization of 2-alkynyl thioanisoles
  作者：Christopher C. Dillon、Bagieng Keophimphone、Melissa Sanchez、Parveen Kaur、Hubert Muchalski

  DOI：10.1039/c8ob02196a

  日期：——

  developed for the construction of a benzo[b]thiophene core via cyclization reaction of alkynes. Although few catalytic reactions were disclosed, most methods rely on stoichiometric activation of alkynes. Here we report an efficient method for the synthesis of 2-substituted benzo[b]thiophenes from 2-alkynyl thioanisoles catalyzed by a gold(I)–IPr hydroxide that is applicable to a wide range of substrates

  苯并[ b ]噻吩杂环是许多重要的小分子药物和候选药物以及有机半导体材料的重要组成部分。已经开发了许多通过炔烃的环化反应来构建苯并[ b ]噻吩核的方法。尽管公开的催化反应很少，但是大多数方法依赖于炔烃的化学计量活化。在这里我们报告了一种由金催化的由2-炔基硫代苯甲醚合成2-取代的苯并[ b ]噻吩的有效方法（I）– IPr氢氧化物，适用于具有多种电子和空间特性的多种底物。另外，我们通过实验证明了酸添加剂及其共轭碱对催化剂周转至关重要。
• Potassium Hydroxide/Dimethyl Sulfoxide Superbase-Promoted Transition Metal-Free Synthesis of 2-Substituted Benzothiophenes under Visible Light
  作者：Li Gao、Bin Chang、Wenzhao Qiu、Lele Wang、Xianzhi Fu、Rusheng Yuan

  DOI：10.1002/adsc.201501136

  日期：2016.4.14

  A potassium hydroxide/dimethyl sulfoxide (KOH/DMSO) superbase‐promoted method for the synthesis of 2‐substituted benzothiophenes has been developed via photoinduced intermolecular annulation of 2‐halothioanisoles with terminal alkynes at ambient temperature. The present protocol uses commercially available 2‐halothioanisoles as substrates and visible light as energy force, which offers a wide range

  氢氧化钾/二甲基亚砜（KOH / DMSO）超碱促进的合成2-取代的苯并噻吩的方法是在环境温度下通过2-卤代硫代苯甲醚与末端炔烃的光诱导分子间环化反应而开发的。本方案使用市售的2-卤代硫代苯甲醚作为底物，使用可见光作为能量，以中度到良好的产率选择性地提供广泛的苯并噻吩区域。这种简便有效的转化将为合成苯并噻吩衍生物提供一种环境友好的方法。
• Efficient Synthesis of Benzothiophenes by an Unusual Palladium-Catalyzed Vinylic CS Coupling
  作者：Christopher S. Bryan、Julia A. Braunger、Mark Lautens

  DOI：10.1002/anie.200902843

  日期：2009.9.7

  construction of a CS and a CC bond under catalytic conditions forms the basis of an efficient route to diversely functionalized benzothiophenes from gem‐dihalovinyl thiophenols. The CC bond can be formed in this tandem catalytic process with an organoboron reagent as shown in the scheme (R1=H, Me, F, Cl, Br, OCH2O; R2=H, Me; R3=aryl, heteroaryl, alkenyl, alkyl), or by Heck or Sonogashira coupling with an

  同时施工一个C  S和一个C 催化条件下C键形成从不同地官能化的苯并噻吩的高效路由的基础宝石-dihalovinyl苯硫酚。与c 可以在此串联与有机硼试剂催化工艺来形成C键为显示在方案（R 1 = H中，Me，F，氯，溴， OCH 2 ö  ; R 2 = H中，Me; R 3＝芳基，杂芳基，烯基，烷基），或通过Heck或Sonogashira与烯烃或炔烃偶联。
• Visible Light Photocatalytic Synthesis of Benzothiophenes
  作者：Durga Prasad Hari、Thea Hering、Burkhard König

  DOI：10.1021/ol302517n

  日期：2012.10.19

  The photocatalytic reaction of o-methylthio-arenediazonium salts with alkynes yields substituted benzothiophenes regioselectively through a radical annulation process. Green light irradiation of eosin Y initiates the photoredox catalysis. The scope of the reaction was investigated by using various substituted diazonium salts and different alkynes.
• Transition-Metal-Free Method for the Synthesis of Benzo[b]thiophenes from o-Halovinylbenzenes and K2S via Direct SNAr-Type Reaction, Cyclization, and Dehydrogenation Process
  作者：Yun Liang、Xiaoyun Zhang、Weilan Zeng、Yuan Yang、Hui Huang

  DOI：10.1055/s-0033-1339289

  日期：——

  A new, highly efficient procedure for the synthesis of benzothiophenes from easily available o-halovinylbenzenes and potassium sulfide has been developed. The reaction tolerated a wide range of functionalities, and various 2-substituted benzo[b]thiophenes are provided in the high yields in the absence of a transition-metal catalyst.