3-(5-溴噻吩-2-)吡啶 | 169050-05-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 3-(5-溴噻吩-2-)吡啶
• 英文名称: 3-(5-bromothiophen-2-yl)pyridine
• CAS: 169050-05-9
• 化学式: C₉H₆BrNS
• 分子量: 240.123
• InChiKey: GJBHIXTYLYHAQD-UHFFFAOYSA-N

物化性质

• 熔点：
  52-54.5°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  3-(5-溴噻吩-2-)吡啶 在 palladium on activated charcoal copper(l) iodide 、 bis(triphenylphosphine)palladium(II)-chloride 、 氢气 、 三乙胺 、 肼 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 58.0h， 生成 4-(5-(pyridin-3-yl)thiophen-2-yl)butylamine
  参考文献：
  名称：

  Synthesis and Antibacterial Activity of Novel C₁₂ Vinyl Ketolides

  摘要：

  A novel series Of C-12 vinyl erythromycin derivatives have been discovered which exhibit in vitro and in vivo potency against key respiratory pathogens. The C-12 modification involves replacing the natural C-12 methyl group in the erythromycin core with a vinyl group via chemical synthesis. From the C-12 vinyl macrolide core, a series Of C-12 vinyl ketolides was prepared. Several compounds were found to be potent against macrolide-sensitive and -resistant bacteria. The C-12 vinyl ketolides 6j and 6k showed a similar antimicrobial spectrum and comparable activity to the commercial ketolide telithromycin. However, the pharmacokinetic profiles Of C-12 vinyl ketolides 6j and 6k in rats differ from that of telithromycin by having higher lung-to-plasma ratios, larger volumes of distribution, and longer half-lives. These pharmacokinetic differences have a pharmacodynamic effect as both 6j and 6k exhibited better in vivo efficacy than telithromycin in rat lung infection models against Streptococcus pneumoniae and Haemophilus influenzae.

  DOI：

  10.1021/jm051157a
• 作为产物：
  描述：

  5-pyrid-3-基噻吩-2-羧酸 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 3-(5-溴噻吩-2-)吡啶
  参考文献：
  名称：

  Decarboxylative Bromination of Heteroarenes: Initial Mechanistic Insights

  摘要：

  在我们实验室最初的报告中描述了各种氮杂环芳烃的无金属脱羧卤代化反应后，我们着手研究这种化学反应发生的可能机制。来自这种机理研究的证据表明，这种化学反应通过自由基途径发生，1H NMR研究表明酸性底物激活了NBS。

  DOI：

  10.1055/s-0040-1707901

文献信息

• A Straightforward Synthesis to Novel 1,10-Phenanthrolines with Fused Thiophene Structure
  作者：Matthias Bauer、Maike Tünnermann、Pia Rehsies、Ulrich Flörke

  DOI：10.1055/s-0037-1611022

  日期：2018.12

  We report here a straightforward synthesis for a series of new structures with fused 1,10-phenanthroline-thiophene connection. They are synthesized with a modified Hinsberg thiophene procedure, followed by successive modification to yield several 5,7-disubstituted thieno[3,4-f][1,10]phenanthrolines, most notable thiophene-substituted compounds that could be potentially of use for organic electronics

  我们在这里报告了一系列具有融合 1,10-菲咯啉-噻吩连接的新结构的直接合成。它们是用改进的 Hinsberg 噻吩程序合成的，然后连续修改以产生几种 5,7-二取代的噻吩并 [3,4-f][1,10] 菲咯啉，最显着的噻吩取代的化合物可能用于有机电子应用。对于一些选定的例子，获得了晶体结构，显示出围绕熔接连接的几乎共面的排列，这也有利于有机电子产品或太阳能电池中的有效电子转移。
• [EN] AN EFFICIENT METHOD FOR SYNTHESIS OF 5-(3-PYRIDYL)-2,2'-BITHIOPHENE(SENSITIZER)<br/>[FR] PROCÉDÉ EFFICACE POUR LA SYNTHÈSE DU 5-(3-PYRIDYL)-2,2'-BITHIOPHÈNE (SENSIBILISATEUR)
  申请人：FERMENTA BIOTECH LTD

  公开号：WO2021019558A1

  公开（公告）日：2021-02-04

  The present invention discloses an efficient process for synthesis of photosensitizer, 5-(3-pyridyl)-2,2'-bithiophene in high yield and purity.

  本发明公开了一种高效合成光敏剂5-(3-吡啶基)-2,2'-双噻吩的高产率和高纯度工艺。
• Orientational self-sorting: formation of structurally defined Pd₄L₈ and Pd₆L₁₂ cages from low-symmetry dipyridyl ligands
  作者：Ru-Jin Li、Adam Marcus、Farzaneh Fadaei-Tirani、Kay Severin

  DOI：10.1039/d1cc03828a

  日期：——

  Structurally defined Pd₄L₈ and Pd₆L₁₂ coordination cages are obtained from low-symmetry dipyridyl ligands.

  从低对称度的二吡啶配体中获得结构定义的Pd₄L₈和Pd₆L₁₂配位笼。
• COMPOUNDS AND METHODS FOR KINASE MODULATION, AND INDICATIONS THEREFOR
  申请人：Ibrahim Prabha N.

  公开号：US20110183988A1

  公开（公告）日：2011-07-28

  Compounds and salts thereof, formulations thereof, conjugates thereof, derivatives thereof, forms thereof and uses thereof are described. In certain aspects and embodiments, the described compounds or salts thereof, formulations thereof, conjugates thereof, derivatives thereof, forms thereof are active on each of B-Raf, B-Raf V600E and c-Raf-1 protein kinase. In certain aspects and embodiments, the described compounds are active in inhibiting proliferation of a Ras mutant cell line. Also described are methods of use thereof to treat diseases and conditions, including melanoma, glioma, glioblastoma, pilocytic astrocytoma, liver cancer, biliary tract cancer, cholangiocarcinoma, colorectal cancer, lung cancer, bladder cancer, gallbladder cancer, breast cancer, pancreatic cancer, thyroid cancer, kidney cancer, ovarian cancer, adrenocortical cancer, prostate cancer, gastrointestinal stromal tumors, medullary thyroid cancer, tumor angiogenesis, acute myeloid leukemia, chronic myelomonocytic leukemia, childhood acute lymphoblastic leukemia, plasma cell leukemia, and multiple myeloma.

  描述了化合物及其盐、制剂、共轭物、衍生物、形式和用途。在某些方面和实施例中，所述的化合物或其盐、制剂、共轭物、衍生物、形式对B-Raf、B-Raf V600E和c-Raf-1蛋白激酶均具有活性。在某些方面和实施例中，所述的化合物在抑制Ras突变细胞系增殖方面具有活性。还描述了使用它们治疗疾病和病况的方法，包括黑色素瘤、胶质瘤、胶质母细胞瘤、毛细胞星形细胞瘤、肝癌、胆管癌、胆管细胞癌、结直肠癌、肺癌、膀胱癌、胆囊癌、乳腺癌、胰腺癌、甲状腺癌、肾癌、卵巢癌、肾上腺皮质癌、前列腺癌、胃肠道间质瘤、髓样甲状腺癌、肿瘤血管生成、急性髓系白血病、慢性髓细胞/单核细胞白血病、儿童急性淋巴细胞白血病、浆细胞白血病和多发性骨髓瘤。
• Regiodivergent Synthesis of Brominated Pyridylthiophenes by Overriding the Inherent Substrate Bias
  作者：Kentaro Okano、Masahiro Hosoya、Atsunori Mori

  DOI：10.1055/a-2106-1678

  日期：2024.3

  pyridylthiophene was switched by changing the reaction conditions, including the metal amide base and the solvent. Subsequently, in situ transmetalation and halogen dance on the corresponding organometallic species were controlled by additives and the reaction temperature, as well as by the above reaction conditions. This method successfully enabled the synthesis of four iodinated constitutional isomers

  完成了吡啶基噻吩支架的区域控制功能化。通过改变反应条件（包括金属酰胺碱和溶剂）来改变吡啶基噻吩去质子化的区域选择性。随后，通过添加剂和反应温度以及上述反应条件来控制相应有机金属物质上的原位金属转移和卤素舞动。该方法成功地从单一起始材料 2-(5-溴-2-噻吩基)吡啶合成了四种碘化结构异构体。