2-bromo-5-(4-ethoxycarbonylphenyl)thiophene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-bromo-5-(4-ethoxycarbonylphenyl)thiophene
• 英文别名: ethyl 4-(5-bromothiophen-2-yl)benzoate
• 化学式: C₁₃H₁₁BrO₂S
• 分子量: 311.199
• InChiKey: QLJRBXQMZLNZDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-5-(4-ethoxycarbonylphenyl)thiophene 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 ethyl 4-(5-(6-bromo-9-butyl-9H-carbazol-3-yl)thiophen-2-yl)benzoate
  参考文献：
  名称：

  以吡啶基和邻苯二酚单元为锚定基团的I / II型杂化染料敏化剂的开发†

  摘要：

  已经开发了具有吡啶基和邻苯二酚单元作为锚定基团的I / II型杂化染料敏化剂，并研究了其在染料敏化太阳能电池（DSSC）中的光伏性能。敏化剂具有通过路易斯酸位点的配位键和TiO 2表面上布朗斯台德酸位点的双齿双核桥接键吸附在TiO 2电极上的能力，这使得可以将电子注入到TiO 2的导带中。通过分子内电荷转移（ICT）激发（I型途径）和染料对TiO 2的光激发作用而形成TiO 2电极电荷转移（DTCT）带（II型途径）。发现吸附在TiO 2膜上的I / II型杂化染料敏化剂表现出源自ICT和DTCT特性的宽的光吸收带。在这里，我们揭示了带有吡啶基和邻苯二酚单元的I / II型杂化染料敏化剂的光物理和电化学性质，以及其在TiO 2膜上的吸附模式，以及在I / II型中的光电性能。 II DSSC，基于光（光吸收和荧光光谱）和电化学测定（循环伏安法），密度泛函理论（DFT）计算，该染料的FT-IR光谱吸附的TiO

  DOI：

  10.1039/c6cp06513a
• 作为产物：
  描述：

  4-碘苯甲酸 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 硫酸 、 silver nitrate 作用下， 以 二甲基亚砜 为溶剂， 生成 2-bromo-5-(4-ethoxycarbonylphenyl)thiophene
  参考文献：
  名称：

  Diarylthiophenes as inhibitors of the pore-forming protein perforin

  摘要：

  Evolution from a furan-containing high-throughput screen (HTS) hit (1) resulted in isobenzofuran-1(3H)-one (2) as a potent inhibitor of the function of both isolated perforin protein and perforin delivered in situ by intact KHYG-1 NK cells. In the current study, structure-activity relationship (SAR) development towards a novel series of diarylthiophene analogues has continued through the use of substituted-benzene and -pyridyl moieties as bioisosteres for 2-thioxoimidazolidin-4-one (A) on a thiophene (B) -isobenzofuranone (C) scaffold. The resulting compounds were tested for their ability to inhibit perforin lytic activity in vitro. Carboxamide (23) shows a 4-fold increase over (2) in lytic activity against isolated perforin and provides good rationale for continued development within this class. (C) 2015 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license.

  DOI：

  10.1016/j.bmcl.2015.12.003

文献信息

• Palladium-Catalyzed Coupling Reactions of Bromothiophenes at the C−H Bond Adjacent to the Sulfur Atom with a New Activator System, AgNO₃/KF
  作者：Kei Kobayashi、Atsushi Sugie、Masabumi Takahashi、Kentaro Masui、Atsunori Mori

  DOI：10.1021/ol052063y

  日期：2005.10.1

  Bromothiophene derivatives react with aryl iodides catalyzed by a palladium complex in the presence of a silver(I) nitrate/potassium fluoride system to induce coupling at the C-H bond, while the carbon-bromine bond is intact. The produced coupling product bearing the C-Br bond allows further palladium-catalyzed C-C bond-forming reactions in reasonable yields.

  [反应：见正文]在硝酸银（I）/氟化钾体系存在下，溴噻吩衍生物与钯配合物催化的芳基碘化物反应，诱导CH键上的偶联，而碳-溴键完好无损。产生的带有C-Br键的偶联产物允许以合理的产率进一步进行钯催化的CC键形成反应。
• Site-selective mono-oxidative addition of active zinc into carbon–bromine bond of dibrominated-thiophenes: preparation of thienylzinc reagents and their applications
  作者：Hye-Soo Jung、Hyun-Hee Cho、Seung-Hoi Kim

  DOI：10.1016/j.tetlet.2012.12.024

  日期：2013.2

  A facile protocol for the preparation of 3-bromo-2-thienylzinc bromide A and 5-bromo-2-thienylzinc bromide B has been developed. It has been successfully accomplished by a site-selective oxidative addition of active zinc into a chemically pseudo-equivalent or equivalent carbon-bromine bond, respectively. The subsequent cross-coupling reactions of the organozincs were also successfully carried out under mild conditions providing the corresponding products in moderate to high yields. (C) 2012 Elsevier Ltd. All rights reserved.
• Scope and Limitations on the Site-selective Cross-couplings of Arylzincs with 2,3- and 2,5-Dibromothiophene
  作者：Hyun-Hee Cho、Seung-Hoi Kim

  DOI：10.5012/bkcs.2014.35.10.3081

  日期：2014.10.20