2-(2-(2-thienyl)ethynyl)benzonitrile | 478801-33-1

• 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-(2-thienyl)ethynyl)benzonitrile
• 英文别名: 2-(2-Thiophen-2-ylethynyl)benzonitrile
• CAS: 478801-33-1
• 化学式: C₁₃H₇NS
• 分子量: 209.271
• InChiKey: KZIPHOWLKYUALQ-UHFFFAOYSA-N

物化性质

• 沸点：
  394.4±22.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  15
• 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：
  52
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-(2-thienyl)ethynyl)benzonitrile 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.12h， 以87%的产率得到2-(5-(thiophen-2-yl)-2H-1,2,3-triazol-4-yl)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
• 作为产物：
  描述：

  2-碘噻吩 、 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63%的产率得到2-(2-(2-thienyl)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。
• Sulfinate-Salt-Mediated Radical Relay Cyclization of Cyclic Ethers with 2-Alkynylbenzonitriles toward 3-Alkylated 1-Indenones
  作者：Xiao-Tong Zhu、Tian-Shu Zhang、Qi Zhao、Pei-Jun Cai、Wen-Juan Hao、Shu-Jiang Tu、Bo Jiang

  DOI：10.1002/asia.201800211

  日期：2018.5.4

  sulfinate salt‐mediated radical relay for the completion of C(sp3)−H bond indenylation of cyclic ethers with readily available 2‐alkynylbenzonitriles by combining silver/tert‐butyl peroxide (TBHP) was established, providing a wide range of 3‐alkylated 1‐indenones with generally good yields. Interestingly, the current reaction system can tolerate an S‐centered radical and a C‐centered radical in one pot

  建立了一种新的亚磺酸盐介导的自由基中继剂，通过结合过氧化银/叔丁基过氧化氢（TBHP）来完成环状醚与易于获得的2-炔基苄腈的C（sp 3）-H键茚基化反应烷基化的1-茚满，收率通常很好。有趣的是，当前的反应系统可以在一个罐中容忍一个以S为中心的自由基和一个以C为中心的自由基，其中以S为中心的自由基促进了以C为中心的自由基的形成，从而在不干扰反应过程的情况下引发了自由基的级联反应。还基于控制实验提出了反应机理。
• Synthesis of Naphthalene Amino Esters by the Blaise Reaction of <i>o</i>-Alkynylarenenitriles
  作者：Karuppusamy Sakthivel、Kannupal Srinivasan

  DOI：10.1021/jo500137m

  日期：2014.4.4

  The action of a Reformatsky reagent on o-alkynylarenenitriles provides a convenient access to naphthalene amino esters via tandem 6-endo-dig carbannulation of in situ generated Blaise reaction intermediates. The products are formed in moderate to good yields with high chemo- and regioselectivity.
• 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.