5-chloro-2-phenylbenzo[b]thiophene | 101219-31-2

• 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: 5-chloro-2-phenylbenzo[b]thiophene
• 英文别名: 2-phenyl-5-chlorobenzo[b]thiophene；5-chloro-2-phenylbenzothiophene；5-Chloro-2-phenyl-1-benzothiophene
• CAS: 101219-31-2
• 化学式: C₁₄H₉ClS
• 分子量: 244.744
• InChiKey: ACAIREUQUMNKTA-UHFFFAOYSA-N

物化性质

• 熔点：
  190-191 °C
• 沸点：
  397.8±22.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  16
• 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：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-氨基-4-氯苯硫醇 在 fluoroboric acid 、 potassium tert-butylate 、 溶剂红 43 、 sodium nitrite 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 18.42h， 生成 5-chloro-2-phenylbenzo[b]thiophene
  参考文献：
  名称：

  Visible Light Photocatalytic Synthesis of Benzothiophenes

  摘要：

  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.

  DOI：

  10.1021/ol302517n

文献信息

• Three-component 2-aryl substituted benzothiophene formation under transition-metal free conditions
  作者：Pengcheng Jiang、Xingzong Che、Yunfeng Liao、Huawen Huang、Guo-Jun Deng

  DOI：10.1039/c6ra07730g

  日期：——

  A base-mediated 2-aryl substituted benzothiophene formation from 2-bromobenzene aldehydes, benzylic esters and elemental sulfur under transition-metal-free conditions is described. Various 2-aryl substituted benzothiophene were efficiently obtained under mild conditions.

  描述了在无过渡金属的条件下由2-溴苯醛，苄基酯和元素硫形成的碱介导的2-芳基取代的苯并噻吩。在温和的条件下有效地获得了各种2-芳基取代的苯并噻吩。
• Nickel-catalyzed and Li-mediated regiospecific C–H arylation of benzothiophenes
  作者：Yorck Mohr、Gaëlle Hisler、Léonie Grousset、Yoann Roux、Elsje Alessandra Quadrelli、Florian M. Wisser、Jérôme Canivet

  DOI：10.1039/d0gc00917b

  日期：——

  A nickel-based catalytic system for the regiospecific C2–H arylation of benzothiophene has been established. NiCl2(bpy) is used as a catalyst in combination with LiHMDS as a base in dioxane. The catalytic system is applicable to a variety of functionalized benzothiophenes, as well as other heteroarenes including thiophene, benzodithiophene, benzofuran and selenophene in combination with iodo aryl electrophiles

  建立了用于苯并噻吩的区域特异性C2-H芳基化的镍基催化体系。NiCl 2（bpy）与LiHMDS作为二恶烷中的碱结合使用。该催化体系适用于各种功能化的苯并噻吩，以及其他杂芳烃，包括噻吩，苯并二噻吩，苯并呋喃和硒烯与碘代芳基亲电试剂的组合。讨论了LiHMDS作为独特有效基础和假定机制的作用。最终证明了该系统对合成活性药物成分中间体的适用性。
• Metalated Porous Phenanthroline‐Based Polymers as Efficient Heterogeneous Catalysts for Regioselective C−H Activation of Heteroarenes
  作者：Yongquan Tang、Zhifeng Dai、Sai Wang、Fang Chen、Xiangju Meng、Feng‐Shou Xiao

  DOI：10.1002/asia.202100695

  日期：2021.9

  Nickel species have been introduced into porous phenanthroline-based organic polymer, which is catalytically active, regioselective, and recyclable for C−H activation of heterocycles. This work offers a new opportunity for design of novel non-noble metal-based heterogeneous catalysts for the regioselective C−H activation of heterocycles.

  镍物种已被引入基于多孔菲咯啉的有机聚合物中，该聚合物具有催化活性、区域选择性和可回收用于杂环的 CH 活化。这项工作为设计用于杂环区域选择性 CH 活化的新型非贵金属基多相催化剂提供了新的机会。
• Synthesis of 2-substituted benzo[b]thiophene via a Pd-catalyzed coupling of 2-iodothiophenol with phenylacetylene
  作者：Jingwen Chen、Haifeng Xiang、Li Yang、Xiangge Zhou

  DOI：10.1039/c6ra26611h

  日期：——

  2-iodothiophenol and phenylacetylene has been developed. A series of 2-substituted benzo[b]thiophenes were obtained in moderate to good yield (up to 87%). The application of this method was demonstrated by the synthesis of 2-(4-(tert-butyl)phenyl)benzo[b]thiophene 1,1-dioxide and (4-methoxyphenyl)(2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)methanone, which exhibit a fluorescence quantum yield of up to 1 and

  已经开发了Pd（II）催化的2-碘硫代苯酚和苯乙炔之间的Sonogashira型交叉偶联反应。以中等至良好的产率（高达87％）获得了一系列2-取代的苯并[ b ]噻吩。该方法的应用程序是由2-（4-（合成证明叔丁基）苯基）苯并[ b ]噻吩-1,1-二氧化物和（4-甲氧基苯基）（2-（4-甲氧基苯基）苯并[ b ]噻吩-3-基）甲酮，其荧光量子产率最高为1，可以分别用作大麻素受体配体。
• Preparation of Benzothiophenes and Benzoselenophenes from Arylamines and Alkynes <i>via</i> Radical Cascade Reactions
  作者：Hao Zang、Jian-Guo Sun、Xin Dong、Ping Li、Bo Zhang

  DOI：10.1002/adsc.201501102

  日期：2016.6.2

  An intermolecular radical cascade reaction between readily prepared o‐methylthio‐arylamines or o‐methylselanyl‐arylamines and alkynes for the preparation of valuable benzothiophenes or benzoselenophenes is reported. These transformations occur efficiently with complete regioselectivity and the products are obtained in moderate to good yields. The current protocol is successfully applied to the synthesis

  据报道，易于制备的邻-甲硫基-芳基胺或邻甲基-硒基-芳基胺与炔烃之间的分子间自由基级联反应可用于制备有价值的苯并噻吩或苯并硒吩。这些转化有效地发生，具有完全的区域选择性，并且以中等至良好的产率获得了产物。当前方案已成功应用于药物雷洛昔芬和AT 1受体拮抗剂的关键中间体的合成。