2-phenyl-5-methylbenzo[b]thiophene | 55164-43-7

• 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: 2-phenyl-5-methylbenzo[b]thiophene
• 英文别名: 5-methyl-2-phenylbenzothiophene；5-methyl-2-phenyl-1-benzothiophene
• CAS: 55164-43-7
• 化学式: C₁₅H₁₂S
• 分子量: 224.326
• InChiKey: LTXFQSPHNSWPDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-phenyl-5-methylbenzo[b]thiophene 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 作用下， 反应 12.0h， 生成 5-(Diethoxyphosphorylmethyl)-2-phenyl-1-benzothiophene
  参考文献：
  名称：

  Synthesis and calcium antagonistic activity of a series of diethyl benzofuryl, benzothienyl and benzogammapyronyl benzylphosphonates

  摘要：

  In this work we present about 15 original heterocyclic diethyl benzylphosphonate analogues of fostedil, in which we have varied the nature of the heterocycle, the substituents or the phosphonic group, or even the position of this latter. Three diethyl 4-(2-benzofuryl) benzyl phosphonates exhibited slightly higher calcium antagonism than the control. Solely substitution with a fluorine atom was able to maintain activity, whereas the other modifications always decreased it.

  DOI：

  10.1016/0223-5234(93)90084-r
• 作为产物：
  描述：

  2-[(4-甲基苯基)硫烷基]-1-苯基乙酮 在 PPA 、 Polyphosphoric acid (PPA) 作用下， 反应 6.0h， 生成 2-phenyl-5-methylbenzo[b]thiophene
  参考文献：
  名称：

  Synthesis and calcium antagonistic activity of a series of diethyl benzofuryl, benzothienyl and benzogammapyronyl benzylphosphonates

  摘要：

  In this work we present about 15 original heterocyclic diethyl benzylphosphonate analogues of fostedil, in which we have varied the nature of the heterocycle, the substituents or the phosphonic group, or even the position of this latter. Three diethyl 4-(2-benzofuryl) benzyl phosphonates exhibited slightly higher calcium antagonism than the control. Solely substitution with a fluorine atom was able to maintain activity, whereas the other modifications always decreased it.

  DOI：

  10.1016/0223-5234(93)90084-r

文献信息

• 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。
• Reaction pathways for the cyclization of ortho-thioalkyl and ortho-thioaryl substituted phenyl radicals with alkynes. Reaction of o-methylthioarenediazonium tetrafluoroborates with alkynes to give 2-substituted benzo[b]thiophenes
  作者：Rino Leardini、Gian Franco Pedulli、Antonio Tundo、Giuseppe Zanardi

  DOI：10.1039/c39850001390

  日期：——

  An easily effected aromatic annelation is described involving reaction of O-thioalkyl and O-thioaryl substituted Phenyl radicals with alkynes to give 2-substituted benzo[b]thiophenes; the mechanism is discussed.

  描述了一种易于实现的芳族芳构化反应，该过程涉及O-硫代烷基和O-硫代芳基取代的苯基与炔烃的反应，生成2-取代的苯并[ b ]噻吩；讨论了该机制。
• Aromatic amine derivative and organic electroluminescent device using the same
  申请人：IDEMITSU KOSAN CO., LTD.

  公开号：US10297765B2

  公开（公告）日：2019-05-21

  Provided are: an aromatic amine derivative in which a terminal substituent such as a dibenzofuran ring or a dibenzothiophene ring is bonded to a nitrogen atom directly or through an arylene group or the like; an organic electroluminescence device including an organic thin film layer formed of one or more layers including a light emitting layer and interposed between a cathode and an anode in which a layer of the organic thin film layer contains the aromatic amine derivative by itself or as a component of a mixture, and the device has a long lifetime and high luminous efficiency; and an aromatic amine derivative for realizing the device.

  提供了一种芳香胺衍生物，其末端取代基（如二苯并呋喃环或二苯并噻吩环）直接或通过芳烯基等与氮原子键合；一种有机电致发光器件，包括一层或多层有机薄膜层，其中包括发光层，并置于阴极和阳极之间，有机薄膜层的一层本身含有或作为混合物的组分含有芳香族胺衍生物，该器件具有长寿命和高发光效率；以及一种用于实现该器件的芳香族胺衍生物。
• Banfield et al., Journal of the Chemical Society, 1956, p. 4791,4798
  作者：Banfield et al.

  DOI：——

  日期：——