5-(thiophen-2-yl)furan-2-carbonitrile | 1020847-49-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 5-(thiophen-2-yl)furan-2-carbonitrile
• 英文别名: 5-Thiophen-2-ylfuran-2-carbonitrile；5-thiophen-2-ylfuran-2-carbonitrile
• CAS: 1020847-49-7
• 化学式: C₉H₅NOS
• 分子量: 175.211
• InChiKey: VUIJLTFXVIGTGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  65.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(thiophen-2-yl)furan-2-carbonitrile 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 sodium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 28.0h， 生成 5-[5-(4-amidinophenyl)-thiophen-2-yl]-furan-2-carboxamidine dihydrochloride
  参考文献：
  名称：

  Dicationic phenyl-2,2′-bichalcophenes and analogues as antiprotozoal agents

  摘要：

  A series of phenyl-2,2'-bichalcophene diamidines 1a-h were synthesized from the corresponding dinitriles either via a direct reaction with LiN(TMS)(2), followed by deprotection with ethanolic HCl or through the bis-O-acetoxyamidoxime followed by hydrogenation in acetic acid and EtOH over Pd-C. These diamidines show a wide range of DNA affinities as judged from their Delta T-m values which are remarkably sensitive to replacement of a furan unit with a thiophene one. These differences are explained in terms of the effect of subtle changes in geometry of the diamidines on binding efficacy. Five of the eight compounds were highly active (below 6 nM IC50) in vitro against Trypanosoma brucei rhodesiense (T. b. r.) and four gave IC(50)values less than 7 nM against Plasmodium falciparum (P. f.). Only one of the compounds was as effective as reference compounds in the T. b. r. mouse model for the acute phase of African trypanosomiasis. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.11.047
• 作为产物：
  描述：

  5-溴-2-呋喃甲醛 在 四(三苯基膦)钯 盐酸羟胺 、 乙酸酐 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 34.0h， 生成 5-(thiophen-2-yl)furan-2-carbonitrile
  参考文献：
  名称：

  Ismail, Mohamed A., Journal of Chemical Research, 2006, # 11, p. 733 - 737

  摘要：

  DOI：

文献信息

• 10.1021/acs.joc.4c00347
  作者：Cigana, Brandon、Lapointe, Victoria、Majewski, Marek B.、Forgione, Pat

  DOI：10.1021/acs.joc.4c00347

  日期：——

  library of 2,5-furan-based phenylene/thiophene oligomers were synthesized starting from 5-bromofurfural, a derivative of biomass-derived furfural. Varied electronic groups are coupled onto the furan motif, followed by the installation of a phenylene or thiophene central linker through a one-pot Pd-catalyzed decarboxylative cross-coupling reaction. Resulting oligomers containing the furan-phenylene-furan

  以 5-溴糠醛（一种生物质衍生的糠醛衍生物）为原料，合成了基于 2,5-呋喃的亚苯基/噻吩低聚物库。将各种电子基团偶联到呋喃基序上，然后通过一锅钯催化的脱羧交叉偶联反应安装亚苯基或噻吩中心连接基。所得含有呋喃-亚苯基-呋喃核心的低聚物在溶液中具有高光致发光量子产率（83-98%），这对于光电器件至关重要。通过改变外围官能团和耦合到呋喃骨架上的中心连接体来调节吸光度和光致发光最大值。
• Ismail, Mohamed A., Journal of Chemical Research, 2006, # 11, p. 733 - 737
  作者：Ismail, Mohamed A.

  DOI：——

  日期：——
• Dicationic phenyl-2,2′-bichalcophenes and analogues as antiprotozoal agents
  作者：Mohamed A. Ismail、Serry A. El Bialy、Reto Brun、Tanja Wenzler、Rupesh Nanjunda、W. David Wilson、David W. Boykin

  DOI：10.1016/j.bmc.2010.11.047

  日期：2011.1

  A series of phenyl-2,2'-bichalcophene diamidines 1a-h were synthesized from the corresponding dinitriles either via a direct reaction with LiN(TMS)(2), followed by deprotection with ethanolic HCl or through the bis-O-acetoxyamidoxime followed by hydrogenation in acetic acid and EtOH over Pd-C. These diamidines show a wide range of DNA affinities as judged from their Delta T-m values which are remarkably sensitive to replacement of a furan unit with a thiophene one. These differences are explained in terms of the effect of subtle changes in geometry of the diamidines on binding efficacy. Five of the eight compounds were highly active (below 6 nM IC50) in vitro against Trypanosoma brucei rhodesiense (T. b. r.) and four gave IC(50)values less than 7 nM against Plasmodium falciparum (P. f.). Only one of the compounds was as effective as reference compounds in the T. b. r. mouse model for the acute phase of African trypanosomiasis. (C) 2010 Elsevier Ltd. All rights reserved.