4-噻吩-2-基嘧啶 | 19084-26-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 4-噻吩-2-基嘧啶
• 英文名称: 4-(thiophene-2-yl)pyrimidine
• 英文别名: 4-(thiophen-2-yl)pyrimidine；4-thiophen-2-yl-pyrimidine；(thienyl-2)-4 pyrimidine；4-(2-thienyl)-pyrimidine；4-(2-thienyl)pyrimidine；4-[2]thienyl-pyrimidine；4-thiophen-2-ylpyrimidine
• CAS: 19084-26-5
• 化学式: C₈H₆N₂S
• mdl: MFCD01859996
• 分子量: 162.215
• InChiKey: BWFAPQRLXWNZLX-UHFFFAOYSA-N

物化性质

• 熔点：
  66-67 °C(Solv: ethyl ether (60-29-7); ligroine (8032-32-4))
• 沸点：
  96-103 °C(Press: 0.03-0.06 Torr)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 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：
  54
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  4-噻吩-2-基嘧啶 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 77.5h， 生成 2-amino-5-[4-(diphenylamino)phenyl]-6-(2-thienyl)pyridine-3-carbonitrile
  参考文献：
  名称：

  2-amino-5-aryl- and 2-amino-5-hetaryl-3-cyano-6-(2-thienyl)pyridines as Organic Dyes for Dye-Sensitized Solar Cells: Synthesis, Quantum-Chemical Calculations, Spectral and Electrochemical Properties

  摘要：

  DOI：

  10.1007/s10593-014-1536-x
• 作为产物：
  描述：

  甲脒 以81%的产率得到
  参考文献：
  名称：

  Gupton John T., Hicks Fred A., Wilkinson Douglas R., Petrich Scott A.,Sik+, Heterocycles, 37 (1994) N 1, S 487-499

  摘要：

  DOI：

文献信息

• Fast and Green One-Pot Multicomponent Synthesis of a Library of Pyrrolo[1,2-c] Pyrimidines Under Microwave Irradiation
  作者：Emilian Georgescu、Florentina Georgescu、Constantin Draghici、Liliana Cristian、Marcel Popa、Florea Dumitrascu

  DOI：10.2174/13862073113169990050

  日期：2013.11

  clean and rapid one-pot three component, microwave-assisted synthesis of pyrrolo[1,2-c]pyrimidine derivatives starting from various substituted pyrimidines, 2-bromoacetophenones and nonsymmetrical, electron deficient alkynes in 1,2-epoxybutane which acts both as solvent and acid scavenger is reported. This one-pot three component synthesis implies short reaction times being at the same time highly cost-effective

  一种简单，清洁，快速的一锅三组分微波辅助合成吡咯并[1,2-c]嘧啶衍生物，其由各种取代的嘧啶，2-溴苯乙酮和不对称的电子缺陷炔烃在1,2-环氧丁烷中起作用既有用作溶剂也有除酸剂的报道。这种一锅三组分的合成方法意味着反应时间短，同时具有很高的成本效益和环境友好性。
• Catalyst free synthesis of mono- and disubstituted pyrimidines from O-acyl oximes
  作者：Atul Upare、Pochampalli Sathyanarayana、Ranjith Kore、Komal Sharma、Surendar Reddy Bathula

  DOI：10.1016/j.tetlet.2018.05.023

  日期：2018.6

  catalyzed transformations of O-acyl oximes to various N-heterocycles are well established. Herein, we report a catalyst free, oxime carboxylate based, three-component condensation method to access mono- and disubstituted pyrimidines. A broad range of substituted pyrimidines were prepared in moderate to excellent yields. Control experiments reveal that in situ generated formamidine is the key intermediate.

  O-酰基肟向各种N-杂环的过渡金属或碘催化的转化是公认的。在本文中，我们报道了一种无催化剂，基于肟羧酸盐的三组分缩合方法，可用于获得单取代和二取代的嘧啶。制备了各种取代的嘧啶，它们的产率中等至优异。对照实验表明，原位生成的甲am是关键中间体。
• One-Pot and Three-Component synthesis of Substituted Pyrimidines Catalysed by Boron Sulfuric Acid under Solvent-Free Conditions
  作者：Mehdi Soheilizad、Mehdi Adib、Sami Sajjadifar

  DOI：10.3184/174751914x14069964360841

  日期：2014.9

  An efficient, simple and one-pot synthesis of pyrimidine derivatives by a three-component reaction of ketones, triethyl orthoformate, and ammonium acetate in the presence of boron sulfuric acid as a reusable and efficient catalyst under solvent-free conditions is reported. The reusability of catalyst, simplicity of the starting materials, short reaction time, one-pot, and good yields of products are

  报道了在无溶剂条件下，在硫酸硼作为可重复使用的高效催化剂存在下，通过酮、原甲酸三乙酯和乙酸铵的三组分反应，高效、简单和一锅法合成嘧啶衍生物。催化剂可重复使用、原料简单、反应时间短、一锅法、产品收率好是主要优点。
• [EN] SUBSTITUTED THIOPHENE DERIVATIVES AS ANTI-CANCER AGENTS<br/>[FR] DERIVES DU THIOPHENE SUBSTITUES EN TANT QU'AGENTS ANTICANCEREUX
  申请人：CHIRON CORP

  公开号：WO2005095386A1

  公开（公告）日：2005-10-13

  The present invention relates to new substituted five-membered compounds and pharmaceutically acceptable salts, esters or prodrugs thereof, compositions of the new compounds together with pharmaceutically acceptable carriers, and uses of the new compounds. The compounds of the invention have the following general formula (I).

  本发明涉及新的取代五元化合物及其药用盐、酯或前药，新化合物与药用载体的组合物，以及新化合物的用途。本发明的化合物具有以下一般式（I）。
• Synthesis, photophysics, and electrochemistry of thiophene–pyridine and thiophene–pyrimidine dyad comonomers
  作者：Andréanne Bolduc、Stéphane Dufresne、Garry S. Hanan、W. G. Skene

  DOI：10.1139/v09-166

  日期：2010.3

  A series of new π-conjugated donor (D) and acceptor (A) dyad comonomers were prepared using Suzuki coupling protocols. The D–A comonomers consisting of thiophene/bithiophene as donors and pyridine/pyrimidine as acceptors were prepared to investigate their photophysical and electrochemical properties. The dyads were spectroscopically confirmed to be highly conjugated. This was further supported by the X-ray crystal structure of the bithophene–pyridine dyad that showed all the heterocycles to be coplanar. It was further found that the fluorescence yields (Φ_fl) of the dyads were highly dependent on the number of thiophenes. The bithiophene derivatives exhibited Φ_fl values ≥ 0.3 while the thiophene derivatives did not fluoresce. The suppressed fluorescence observed for the thiophene derivatives was due to their higher triplet energy resulting in efficient intersystem crossing (ISC) to the triplet state with Φ_ISC ≥ 0.8. This was confirmed both by time-resolved and steady-state measurements. The singlet excited state of both thiophene and bithiophene dyads was deactivated solely by either fluorescence and (or) ISC. Owing to their donor and acceptor character, the dyads could be oxidized and reduced both electrochemically and photochemically to afford the radical cation and anion, respectively.

  利用铃木偶联协议制备了一系列新的π-共轭供体（D）和受体（A）二元共聚物。以噻吩/联噻吩为给体，吡啶/嘧啶为受体制备了 D-A 共聚单体，以研究它们的光物理和电化学性质。这些二元体经光谱证实具有高度共轭性。双噻吩-吡啶二元化合物的 X 射线晶体结构进一步证实了这一点，该结构显示所有杂环都是共面的。研究还发现，二元化合物的荧光产率（Φfl）与噻吩的数量密切相关。噻吩衍生物的 Φfl 值≥ 0.3，而噻吩衍生物则不产生荧光。噻吩衍生物的荧光被抑制的原因是它们的三重态能量较高，从而导致高效的系统间交叉（ISC）到三重态（ΦISC ≥ 0.8）。时间分辨和稳态测量都证实了这一点。噻吩和双噻吩二元体的单线激发态仅通过荧光和（或）ISC 失活。由于其供体和受体特性，二元化合物可以通过电化学和光化学方式氧化和还原，分别产生自由基阳离子和阴离子。