2-(2-(4-nitrophenyl)ethynyl)benzonitrile | 1192716-68-9

• 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-(2-(4-nitrophenyl)ethynyl)benzonitrile
• 英文别名: 2-[2-(4-Nitrophenyl)ethynyl]benzonitrile
• CAS: 1192716-68-9
• 化学式: C₁₅H₈N₂O₂
• 分子量: 248.241
• InChiKey: KSRVYQGNAKIXMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-(4-nitrophenyl)ethynyl)benzonitrile 在 sodium azide 、 zinc dibromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以30%的产率得到5-(4-nitrophenyl)tetrazolo[5,1-a]isoquinoline
  参考文献：
  名称：

  Microwave-assisted cycloadditions of 2-alkynylbenzonitriles with sodium azide: selective synthesis of tetrazolo[5,1-a]pyridines and 4,5-disubstituted-2H-1,2,3-triazoles

  摘要：

  Under microwave irradiation (75 W), treatment of 2-alkynylbenzonitriles with 1.5 equiv of sodium azide in DMSO at 140 degrees C gave 4,5-disubstituted-2H-1,2,3-triazoles in 60-99% yields. Additionally, adding 8 equiv of ZnBr2 and using 8 equiv of sodium azide in DMF at 100 degrees C lead to the formation of tetrazolo[5,1-a]isoquinolines up to 87% yield. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.009
• 作为产物：
  描述：

  4-硝基碘苯 、 2-乙炔基苯甲腈 在 copper(l) iodide 、 四(三苯基膦)钯 、 正丁胺 作用下， 以 乙醚 为溶剂， 反应 4.0h， 以61%的产率得到2-(2-(4-nitrophenyl)ethynyl)benzonitrile
  参考文献：
  名称：

  Microwave-assisted cycloadditions of 2-alkynylbenzonitriles with sodium azide: selective synthesis of tetrazolo[5,1-a]pyridines and 4,5-disubstituted-2H-1,2,3-triazoles

  摘要：

  Under microwave irradiation (75 W), treatment of 2-alkynylbenzonitriles with 1.5 equiv of sodium azide in DMSO at 140 degrees C gave 4,5-disubstituted-2H-1,2,3-triazoles in 60-99% yields. Additionally, adding 8 equiv of ZnBr2 and using 8 equiv of sodium azide in DMF at 100 degrees C lead to the formation of tetrazolo[5,1-a]isoquinolines up to 87% yield. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.009

文献信息

• A radical cyclization cascade of 2-alkynylbenzonitriles with sodium arylsulfinates
  作者：Bang Zhou、Wenqi Chen、Yuzhong Yang、Yuan Yang、Guobo Deng、Yun Liang

  DOI：10.1039/c8ob02288g

  日期：——

  We report an efficient approach to synthesize sulfonated indenones via a radical cascade cyclization of 2-alkynylbenzonitriles with sodium arylsulfinates.

  我们报告了一种高效的方法，通过2-炔基苯甲腈与苯基亚磺酸钠的自由基级联环化合成磺化吲哚酮。
• Catalyst-Controlled Regioselective Approach to 1-Aminoisoquinolines and/or 1-Aminoisoindolines through Aminative Domino Cycliza­tion of 2-Alkynylbenzonitriles
  作者：Virsinha Reddy、Abhijeet S. Jadhav、Ramasamy Vijaya Anand

  DOI：10.1002/ejoc.201501390

  日期：2016.1

  A metal-catalyzed regioselective approach towards the synthesis of 1-aminoisoquinolines and/or 1-aminoisindolines through aminative domino cyclization of 2-alkynylbenzonitriles with secondary amines has been developed under solvent-free conditions. It was found that the regioselectivity of the reaction was greatly influenced by the choice of the metal catalyst. Copper-based catalysts favored 6-endo-dig

  已经在无溶剂条件下开发了一种金属催化的区域选择性方法，用于通过 2-炔基苄腈与仲胺的氨基化多米诺环化来合成 1-氨基异喹啉和/或 1-氨基异吲哚啉。发现反应的区域选择性受金属催化剂的选择影响很大。铜基催化剂有利于 6-endo-dig 环化产生 1-氨基异喹啉，而其他催化剂如 Zn、Ag、Bi、Sc 和 Yb 的三氟甲磺酸盐有利于通过 5-exo-dig 环化形成 1-氨基异二氢吲哚。
• Microwave-assisted cycloadditions of 2-alkynylbenzonitriles with sodium azide: selective synthesis of tetrazolo[5,1-a]pyridines and 4,5-disubstituted-2H-1,2,3-triazoles
  作者：Chih-Wei Tsai、Shyh-Chyun Yang、Ya-Ming Liu、Ming-Jung Wu

  DOI：10.1016/j.tet.2009.08.009

  日期：2009.10

  Under microwave irradiation (75 W), treatment of 2-alkynylbenzonitriles with 1.5 equiv of sodium azide in DMSO at 140 degrees C gave 4,5-disubstituted-2H-1,2,3-triazoles in 60-99% yields. Additionally, adding 8 equiv of ZnBr2 and using 8 equiv of sodium azide in DMF at 100 degrees C lead to the formation of tetrazolo[5,1-a]isoquinolines up to 87% yield. (C) 2009 Elsevier Ltd. All rights reserved.