4-bromo-2-phenylthiophene | 38071-58-8

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 4-bromo-2-phenylthiophene
• 英文别名: 4-Brom-2-phenyl-thiophen
• CAS: 38071-58-8
• 化学式: C₁₀H₇BrS
• 分子量: 239.136
• InChiKey: JJCSNFCDSZARRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• 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

• 作为反应物：
  描述：

  4-bromo-2-phenylthiophene 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium tetrahydroborate 、 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到2-苯基噻吩
  参考文献：
  名称：

  NaBH4-TMEDA and a palladium catalyst as efficient regio- and chemoselective system for the hydrodehalogenation of halogenated heterocycles

  摘要：

  DOI：

  10.1016/j.molcata.2014.06.012
• 作为产物：
  描述：

  4-bromo-2-(1-cyclohexenyl)thiophene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 5.5h， 以79%的产率得到4-bromo-2-phenylthiophene
  参考文献：
  名称：

  Javelin-, Hockey Stick-, and Boomerang-Shaped Liquid Crystals. Structural Variations on p-Quinquephenyl

  摘要：

  The ramifications of changing molecular geometry in a series of all-aromatic liquid crystals derived from p-quinquephenyl are reported. Substituting heterocyclic rings such as thiophene, oxadiazole, oxazole, or 1,3-phenylene into the p-quinquephenylene core affects molecular shape changes via the substituent's exocyclic bond angle. In general, we found that introducing nonlinearity into molecules depresses the melting transition temperature. The symmetric (boomerang-shaped) molecules, 2,5-bisbiphenyl-4-yl-1,3,4-oxadiazole, 2,5-bisbiphenyl-4-yl-oxazole, and 1,3-bisbiphenyl-4-yl-benzene, melt into isotropic phases showing small monotropic mesophases. By contrast, the asymmetric (hockey stick-shaped) mesogens, 2-terphenyl-4-yl-5-phenyl thiophene and 2-terphenyl-4-yl-5-phenyl-1,3,4-oxadiazole, exhibit more stable enantiotropic liquid crystalline phases. The hockey stick-shaped mesogens exhibit a smectic phase as well as a nematic phase. High-temperature X-ray determination of the smectic layer spacing gives an unambiguous picture of interdigitated, bilayerlike supramolecular architecture in the smectic phase. There are associated changes in the mesogen's electrostatic profile when a heterocycle is introduced into the quinquiphenylene framework (e.g., conjugation is perturbed). Our findings suggest that steric packing considerations dominate the phase preferences (nematic versus smectic phases), However, electronic considerations (conjugation) appear to control the range of mesomorphism in this new family of nonlinear liquid crystals.

  DOI：

  10.1021/jp010869j

文献信息

• [EN] METABOTROPIC GLUTAMATE RECEPTOR NEGATIVE ALLOSTERIC MODULATORS (NAMS) AND USES THEREOF<br/>[FR] MODULATEURS ALLOSTÉRIQUES NÉGATIFS (NAM) DU RÉCEPTEUR MÉTABOTROPIQUE DU GLUTAMATE ET UTILISATIONS DE CEUX-CI
  申请人：SANFORD BURNHAM MED RES INST

  公开号：WO2015191630A1

  公开（公告）日：2015-12-17

  Provided herein are small molecule active metabotropic glutamate subtype-2 and -3 receptor negative allosteric modulators (NAMs), compositions comprising the compounds, and methods of using the compounds and compositions.

  本文提供了小分子活性代谢型谷氨酸亚型-2和-3受体负向变构调节剂（NAMs），包括这些化合物的组合物，以及使用这些化合物和组合物的方法。
• Sensitive Assays by Nucleophile-Induced Rearrangement of Photoactivated Diarylethenes
  作者：Sebastian Fredrich、Aurelio Bonasera、Virginia Valderrey、Stefan Hecht

  DOI：10.1021/jacs.8b02982

  日期：2018.5.23

  Upon light-induced isomerization, diarylethenes (DAEs) equipped with reactive aldehyde moieties rearrange selectively in the presence of amines, accompanied by decoloration. In a comprehensive study, the probe structure was optimized with regard to its inherent reactivity in the nucleophile-triggered rearrangement reaction. Detailed structure-reactivity relationships could be derived, in particular

  在光诱导异构化后，带有反应性醛部分的二芳基乙烯 (DAE) 在胺存在下选择性地重排，并伴有脱色。在一项综合研究中，探针结构根据其在亲核试剂触发的重排反应中的固有反应性进行了优化。可以推导出详细的结构-反应关系，特别是关于整合（杂）芳基部分的类型以及甲酰基残基的位置，并且优化了探针与伯胺和仲胺的固有反应性。利用辅助碱基，最初形成的重排产物可以参与随后的催化循环，导致放大的脱色过程。这种额外的催化途径使我们能够提高我们方法的灵敏度并成功区分胺和硫醇。此外，已设计出表现出强分析物诱导荧光调制的探针，以通过使用更灵敏的读数进一步降低检测限。优化的 DAE 探针是未来可编程传感材料和设备的有前途的分子组件。
• Construction of Thienothiophene and Thienofuran Ring Systems via Ring Expansion of Difluorothiiranes Generated from Dithioesters
  作者：Kohei Fuchibe、Ibuki Mukohara、Atsushi Yamada、Daisuke Miyazaki、Ryo Takayama、Junji Ichikawa

  DOI：10.1021/acs.orglett.1c03805

  日期：2022.1.14

  The reaction of aryl thiophene-2-carbodithioates or thiophene-3-carbodithioates with difluorocarbene generated from BrCF2CO2Li/molecular sieves 4A produced arylsulfanylated 2,2-difluoro-3-thienylthiiranes. In the presence of lithium ion, the thiirane intermediates underwent ring expansion followed by HF elimination, leading to fluorinated thieno[3,2-b]thiophenes or thieno[2,3-b]thiophenes. The reactions

  芳基噻吩-2-碳二硫酸酯或噻吩-3-二硫代碳酸酯与由 BrCF 2 CO 2 Li/分子筛 4A 生成的二氟卡宾反应产生芳基硫烷基化 2,2-二氟-3-噻吩基硫杂环丙烷。在锂离子存在的情况下，硫杂丙环中间体经历扩环然后消除HF，产生氟化噻吩并[3,2- b ]噻吩或噻吩并[2,3- b ]噻吩。氧类似物芳基呋喃碳二硫酸酯的反应也进行得到相应的噻吩并[3,2- b]呋喃。生成的芳基硫烷基（氟）噻吩并呋喃中的分子内氟取代允许构建另一个噻吩环，从而合成稠合的五环噻吩并呋喃。
• ORGANIC COMPOUND, ORGANIC THIN FILM, AND ELECTRONIC DEVICE
  申请人：Samsung Electronics Co., Ltd.

  公开号：US20190036037A1

  公开（公告）日：2019-01-31

  Disclosed are an organic compound selected from a compound represented by Chemical Formula 1A, a compound represented by Chemical Formula 1B, and a combination thereof, an organic thin film including the organic compound, an organic thin film transistor, and an electronic device. The organic compound has liquid crystal properties and exhibits an ordered liquid crystal phase when being heated in a liquid crystal period due to asymmetric substituents and thereby charge mobility may be further improved.

  揭示了一种有机化合物，选择自化学式1A代表的化合物，化学式1B代表的化合物，或两者的组合，包括该有机化合物的有机薄膜，有机薄膜晶体管和电子设备。该有机化合物具有液晶特性，在液晶期间加热时显示有序液晶相，由于不对称的取代基，因此可以进一步提高电荷迁移率。
• Palladium‐Catalyzed Synthesis of Heteroarene‐Fused Cyclooctatetraenes through Dehydrogenative Cyclodimerization
  作者：Keita Fukuzumi、Yuji Nishii、Masahiro Miura

  DOI：10.1002/anie.201707515

  日期：2017.10.2

  architectures. Considerable attention has been paid to the transition‐metal‐mediated synthesis of these cyclic compounds; however, there have been limited achievements to date in the efficient construction of heteroarene‐fused COTs. In this contribution, we report a novel Pd‐catalyzed dehydrogenative cyclodimerization of biheteroarenes through four‐fold C−H activation toward the synthesis of a series

  芳烃稠合的环辛酸酯（COT）具有独特的结构和电子特性，其源自鞍形π共轭体系。这些环状化合物的过渡金属介导的合成已引起相当大的关注。但是，迄今为止，在有效构建杂芳烃融合的COT方面取得的成就有限。在这项贡献中，我们报告了新型的Pd催化的双杂芳烃的脱氢环二聚反应，其通过四倍的CH活化作用来合成一系列杂芳烃融合的COT。一系列的机理研究表明，二价化事件之前，高价Pd物质参与了催化循环。还简要描述了获得的COT的氧化还原行为。