2-(thiophen-2-yl)-4H-[1,2,4]-triazolo[1,5-a]benzimidazole | 428474-60-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-(thiophen-2-yl)-4H-[1,2,4]-triazolo[1,5-a]benzimidazole
• 英文别名: 2-(2-thienyl)-4H-[1,2,4]triazolo[1,5-a]benzimidazole；2-(thiophen-2-yl)-4H-benzimidazo[1,2-b][1,2,4]triazole；Cambridge id 6464346；2-thiophen-2-yl-1H-[1,2,4]triazolo[1,5-a]benzimidazole
• CAS: 428474-60-6
• 化学式: C₁₂H₈N₄S
• 分子量: 240.288
• InChiKey: FNIVKPMAGUWRKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(thiophen-2-yl)-4H-[1,2,4]-triazolo[1,5-a]benzimidazole 、 碘甲烷 在 potassium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 以72%的产率得到4-methyl-2-(2-thienyl)-4H-[1,2,4]triazolo[1,5-a]benzimidazole
  参考文献：
  名称：

  2-aryl(hetaryl)-4H-[1,2,4]triazolo[1,5-a]benzimidazoles

  摘要：

  2-(4-Methylphenyl)-4H-[1,2,4]triazolo[1,5-a]benzimidazole and its previously unknown 2-(2-furyl)- and 2-(2-thienyl)-substituted analogs were synthesized by cyclization of benzimidazole-1,2-diamine with the corresponding carboxylic acid chlorides. The IR, H-1, C-13, and N-15 NMR, and mass spectra of the cyclization products in combination with the results of quantum-chemical calculations of NMR chemical shifts showed radical differences of [1,2,4]triazolo[1,5-a]benzimidazoles having no substituent on N-4 from the recently reported low-melting products of oxidation of 2-amino-1-arylmethylideneaminobenzimidazoles with (diacetoxy-lambda(3)-iodanyl)benzene, which, as we believe, were erroneously assigned analogous structure.

  DOI：

  10.1134/s107042801306016x
• 作为产物：
  描述：

  N-(1H-benzo[d]imidazol-2-yl)thiophene-2-carboximidamide 在 potassium tert-butylate 、 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.67h， 以97%的产率得到2-(thiophen-2-yl)-4H-[1,2,4]-triazolo[1,5-a]benzimidazole
  参考文献：
  名称：

  [1,2,4]三唑并[1,5-a]苯并恶唑的合成由无过渡金属的氧化NN键形成

  摘要：

  已开发出无过渡金属的NCS氧化NN键的形成策略，以有效地生成各种结构有趣的[1,2,4]三唑并[1,5-a]苯并恶唑。已经研究了关键的氧化NN键形成的机理。

  DOI：

  10.1039/c6cc01976e

文献信息

• [EN] COMPOUNDS FOR TREATING DUCHENNE MUSCULAR DYSTROPHY<br/>[FR] COMPOSÉS POUR TRAITER LA DYSTROPHIE MUSCULAIRE DE DUCHENNE
  申请人：SUMMIT CORP PLC

  公开号：WO2009013477A1

  公开（公告）日：2009-01-29

  Compounds of general formula (I), wherein X1, X2, X3, R1, R2, R3, Y and Z are as defined herein are useful for the treatment and prevention of Duchenne muscular dystrophy, Becker muscular dystrophy and cachexia.

  通式（I）的化合物，其中X1、X2、X3、R1、R2、R3、Y和Z的定义如本文所述，对于治疗和预防杜兴氏肌肉萎缩症、贝克氏肌肉萎缩症和消瘦症是有用的。
• COMPOUNDS FOR TREATING DUCHENNE MUSCULAR DYSTROPHY
  申请人：Summit Corporation Plc

  公开号：EP2167508A1

  公开（公告）日：2010-03-31
• Syntheses of [1,2,4]triazolo[1,5-a]benzazoles enabled by the transition-metal-free oxidative N–N bond formation
  作者：Erchang Shang、Junzhi Zhang、Jinyi Bai、Zhan Wang、Xiang Li、Bing Zhu、Xiaoguang Lei

  DOI：10.1039/c6cc01976e

  日期：——

  A transition-metal-free NCS oxidized N-N bond formation strategy has been developed to generate various structurally interesting [1,2,4]triazolo[1,5-a]benzazoles efficiently. The mechanism of the key oxidative N-N bond formation has been investigated...

  已开发出无过渡金属的NCS氧化NN键的形成策略，以有效地生成各种结构有趣的[1,2,4]三唑并[1,5-a]苯并恶唑。已经研究了关键的氧化NN键形成的机理。
• 2-aryl(hetaryl)-4H-[1,2,4]triazolo[1,5-a]benzimidazoles
  作者：A. S. Morkovnik、T. A. Kuz’menko、L. N. Divaeva、G. S. Borodkin

  DOI：10.1134/s107042801306016x

  日期：2013.6

  2-(4-Methylphenyl)-4H-[1,2,4]triazolo[1,5-a]benzimidazole and its previously unknown 2-(2-furyl)- and 2-(2-thienyl)-substituted analogs were synthesized by cyclization of benzimidazole-1,2-diamine with the corresponding carboxylic acid chlorides. The IR, H-1, C-13, and N-15 NMR, and mass spectra of the cyclization products in combination with the results of quantum-chemical calculations of NMR chemical shifts showed radical differences of [1,2,4]triazolo[1,5-a]benzimidazoles having no substituent on N-4 from the recently reported low-melting products of oxidation of 2-amino-1-arylmethylideneaminobenzimidazoles with (diacetoxy-lambda(3)-iodanyl)benzene, which, as we believe, were erroneously assigned analogous structure.