6-chloro-2-phenylbenzo[b]thiophene | 92014-00-1

• 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: 6-chloro-2-phenylbenzo[b]thiophene
• 英文别名: 2-phenyl-6-chlorobenzo[b]thiophene；6-Chloro-2-phenyl-1-benzothiophene
• CAS: 92014-00-1
• 化学式: C₁₄H₉ClS
• 分子量: 244.744
• InChiKey: SMVANLJYQJREER-UHFFFAOYSA-N

物化性质

• 熔点：
  192.6-194.8 °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：

  4-chloro-2-(methylthio)aniline 在 fluoroboric acid 、 溶剂红 43 、 sodium nitrite 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 14.67h， 生成 6-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

• 一种苯并噻吩类化合物的制备方法及其净化提 纯方法
  申请人：温州大学

  公开号：CN103724319B

  公开（公告）日：2016-06-29

  本发明公开了一种苯并噻吩类化合物的制备方法，其步骤包括：以1-溴（氯）-2-苯乙烯基苯或其衍生物为底物，在底物中加入硫化试剂，以二甲基亚砜溶液为溶剂，并在醌类氧化剂、铜催化剂的氧化下经加热反应制得粗产品，然后对粗产品进行净化提纯，其步骤包括对粗产品进行过滤、除溶剂，获得剩余物；对剩余物采用硅胶柱层析，经洗脱液淋洗，收集流出液；合并含有产物的流出液；对合并后的流出液进行浓缩去溶剂，最后经真空干燥得到目标产物。本发明具有工艺流程简单、成本低、产率高的优点。
• 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。
• Copper-Catalyzed Synthesis of Benzo[<i>b</i>]thiophenes and Benzothiazoles Using Thiocarboxylic Acids as a Coupling Partner
  作者：Hui Yu、Meishu Zhang、Yuzhe Li

  DOI：10.1021/jo401353w

  日期：2013.9.6

  copper-catalyzed approach to benzo[b]thiophene and benzothiazole derivatives using thiocarboxylic acids as a sulfur source has been developed. In the presence of CuI and 1,10-phen, and n-Pr3N as the base, (2-iodobenzyl)triphenylphosphonium bromide and (2-iodophenylimino)triphenylphosphorane reacted smoothly with thiocarboxylic acids to give benzo[b]thiophene and benzothiazole derivatives in good yields via

  已经开发出一种有效的铜催化方法，以硫代羧酸作为硫源，用于苯并[ b ]噻吩和苯并噻唑衍生物。在CuI和1,10-phen和n -Pr 3 N为碱的情况下，（2-碘苄基）三苯基溴化and和（2-碘苯基亚氨基）三苯基phosph与硫代羧酸平稳反应，生成苯并[ b ]噻吩和苯并噻唑通过顺序的Ullmann型C–S键耦合和Wittig缩合，可以得到高收率的衍生物。
• 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。
• 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.