2-(2-(2-(methyl)phenyl)ethynyl)benzonitrile | 1192716-71-4

• 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-(methyl)phenyl)ethynyl)benzonitrile
• CAS: 1192716-71-4
• 化学式: C₁₆H₁₁N
• 分子量: 217.27
• InChiKey: IVSBLGNLRJGMKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  23.79
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(2-(2-(methyl)phenyl)ethynyl)benzonitrile 在 sodium azide 、 zinc dibromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以63%的产率得到5-(2-(methyl)phenyl)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：

  2-碘代甲苯 、 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49%的产率得到2-(2-(2-(methyl)phenyl)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

• Copper-Catalyzed Radical Cascade Cyclization To Access 3-Sulfonated Indenones with the AIE Phenomenon
  作者：Kai Sun、Xiao-Lan Chen、Shi-Jun Li、Dong-Hui Wei、Xiao-Ceng Liu、Yin-Li Zhang、Yan Liu、Lu-Lu Fan、Ling-Bo Qu、Bing Yu、Kai Li、Yuan-Qiang Sun、Yu-Fen Zhao

  DOI：10.1021/acs.joc.8b02175

  日期：2018.12.7

  efficient copper-catalyzed radical cascade cyclization strategy was developed, by which a wide variety of 3-sulfonyl substituted indenones were prepared in one pot via reaction of 2-alkynylbenzonitriles with sulfonyl hydrazides in the presence of TBHP and CuI under mild reaction conditions. Much more importantly, the 3-sulfonyl indenones, synthesized through our newly developed copper-catalyzed radical

  开发了一种有效的铜催化自由基级联环化策略，通过在温和的反应条件下，在TBHP和CuI存在下，通过2-炔基苄腈与磺酰肼的反应，在一个罐中制备了多种3-磺酰基取代的茚满酮。更重要的是，通过我们新开发的铜催化的自由基级联环化策略合成的3-磺酰基茚满具有典型的聚集诱导发射（AIE）特性，显示出橙色到红色的发射，并具有较大的斯托克斯位移（大于135）纳米）。此外，这种新发现的AIEgens可以成功地用于活细胞成像，具有出色的生物相容性和应用潜力。
• A unified approach to benzo[<i>c</i>]phenanthridines <i>via</i> the cascade dual-annulation/formylation of 2-alkynyl/alkenylbenzonitriles
  作者：Shalini Verma、Manoj Kumar、Akhilesh K. Verma

  DOI：10.1039/d3cc00197k

  日期：——

  A base-mediated versatile cascade dual-annulation and formylation of 2-alkenyl/alkynylbenzonitriles with 2-methylbenzonitriles has been established for the construction of four different classes of amino and amido substituted benzo[c]phenanthridines and benzo[c]phenanthrolines. The synthesized molecules could be of utmost relevance in pharmaceuticals. The transformation uses the solvent DMF as the

  已经建立了碱基介导的多功能级联双环化和 2-烯基/炔基苯甲腈与 2-甲基苯甲腈的甲酰化，用于构建四种不同类别的氨基和酰氨基取代的苯并 [c] 菲啶和苯并 [c]菲咯啉。合成的分子可能在药物中具有最大的相关性。该转化使用溶剂 DMF 作为甲酰源，用于合成酰胺基取代的支架。这种无过渡金属的独特策略能够在室温下在一个锅中形成多个 C-C 和 C-N 键。
• 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.
• Platinum(II)-catalyzed intramolecular cyclization of alkynylbenzonitriles: synthesis of 1-alkoxyisoquinolines and isoquinolones
  作者：Jim Li、Lijing Chen、Elbert Chin、Alfred S. Lui、Hasim Zecic

  DOI：10.1016/j.tetlet.2010.09.136

  日期：2010.12

  A facile synthesis of a series of 1-alkoxyisoguinolines and (2H)-isoguinolones by an intramolecular 6-endo-dig cyclization of ortho-alkynylbenzonitriles in the presence of a catalytic amount of hydrido(dimethylphosphinous acid-kappa P)[hydrogen bis(dimethylphosphinito-kappa P)]platinum(II) in various alcohols at 65-90 degrees C is described for the first time. (C) 2010 Elsevier Ltd. All rights reserved.
• 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.