N-(2-cyanophenyl)formamide | 53902-59-3

• 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: N-(2-cyanophenyl)formamide
• 英文别名: N-formylanthranilonitrile；N-formyl-anthranilonitrile；N-Formyl-anthranilonitril；Ameisensaeure-(2-cyan-anilid)
• CAS: 53902-59-3
• 化学式: C₈H₆N₂O
• 分子量: 146.148
• InChiKey: VQXREYMEKBSLCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(2-cyanophenyl)formamide 在 氯化亚砜 作用下， 反应 20.0h， 生成 2-氰基苯基异氰酸酯
  参考文献：
  名称：

  Vibrational spectroscopic studies and ab initio calculations of 2-cyanophenylisocyanid dichloride

  摘要：

  FT-Raman and FT-IR spectra of 2-cyanophenylisocyanid dichloride were recorded and analyzed. The vibrational frequencies of the title compound have been computed using the Hartree-Fock/6-31G(*) basis and compared with the experimental values. The prepared compound was identified by NMR and mass spectra. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2006.08.045
• 作为产物：
  描述：

  N-formylindazole 在 (THF)Li(TMP)Zn(tBu)2 作用下， 以 四氢呋喃 为溶剂， 生成 N-(2-cyanophenyl)formamide
  参考文献：
  名称：

  Alkali-metal mediated zincation of N-heterocyclic substrates using the lithium zincate complex, (THF)Li(TMP)Zn(tBu)2 and applications in in situ cross coupling reactions

  摘要：

  This study investigates the ability of the mixed-metal reagent [Li(TMP)Zn(tBu)(2)] 1 to promote direct Zn-H exchange reactions (zincations) of a wide range of N-heterocyclic molecules. The generated metallated intermediates from these reactions are intercepted with I-2 and some of them are also employed as precursors in Pd-catalysed Negishi cross-coupling applications. A comparison with recent precedents in metallation chemistry reveals that for some of these heterocycles, 1 allows improved conversions, under milder conditions and in certain cases, even gives unique regioselectivities. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.090

文献信息

• Mn-promoted Aerobic Oxidative C–C Bond Cleavage of Aldehydes with Dioxygen Activation: A Simple Synthetic Approach to Formamides
  作者：Chun Zhang、Zejun Xu、Tao Shen、Guolin Wu、Liangren Zhang、Ning Jiao

  DOI：10.1021/ol300781s

  日期：2012.5.4

  cleavage of aldehydes with dioxygen activation has been developed. The usage of molecular oxygen (1 atm) as oxidant, reactant, and an initiator to trigger this transformation makes this transformation very green and practical. A plausible radical process is proposed on the basis of mechanistic studies. Furthermore, this method provides a practical, neutral, and mild synthetic approach to formamides

  已经开发了一种新型的Mn促进具有双氧活化作用的醛的需氧氧化CC键断裂。使用分子氧（1个大气压）作为氧化剂，反应物和引发剂来触发这种转变，使这种转变非常绿色和实用。在机理研究的基础上提出了一个可能的基本过程。此外，该方法为甲酰胺提供了一种实用，中性和温和的合成方法，甲酰胺是生物活性分子中的重要单元。
• The conversion of 2-cyano cyanothioformanilides into 3-aminoindole-2-carbonitriles using triphenylphosphine
  作者：Panayiotis A. Koutentis、Sophia S. Michaelidou

  DOI：10.1016/j.tet.2010.06.020

  日期：2010.8

  react with triphenylphosphine and p-toluenesulfonic acid in MeOH to give 3-aminoindole-2-carbonitriles 2b–f in 63–75% yields. Under analogous conditions 2-cyano-4,5-dimethoxyphenyl cyanothioformanilide 2g gives only 4,5-dimethoxyanthranilonitrile 8g and 4,6,7-trimethoxyquinazoline-2-carbonitrile 14g, but in refluxing dry PhMe in the absence of p-toluenesulfonic acid 2-cyano-4,5-dimethoxyphenyl cyanothioformanilide

  2-氰基cyanothioformanilide 3A与在水的存在下发生反应的三苯基膦，得到2-（氰基亚甲基氨基）苄腈4a中，2-（cyanomethylamino）苄腈5，3-氨基吲哚-2-甲腈2A和（2-氰基吲哚-3-基）iminotriphenylphosphorane 6a。在对甲苯磺酸在MeOH中的存在下，2-氰基氰基硫代甲酰甲酰胺3a与三苯基膦（2当量）之间的反应以90％的产率得到3-氨基吲哚-2-腈2a。在相同条件下，2-（氰基亚甲基氨基）苄腈4a得到蒽腈8a，3-氨基吲哚-2-腈2a和N-（2-氰基苯基）甲酰胺9。此外，取代的2-氰基氰基硫代甲酰胺基化物3b - f与三苯基膦和对甲苯磺酸在MeOH中反应，以63-75％的收率得到3-氨基吲哚-2-腈2b - f。在类似条件下，2-氰基-4,5-二甲氧基苯基氰基硫代甲酰苯胺2g仅产生4,5-二甲氧基蒽腈8g和4,6,7-三甲氧
• The Reaction of 2-(Acylamino)benzonitriles with Primary Aromatic Amines: A Convenient Synthesis of 2-Substituted 4-(Arylamino)quinazolines
  作者：Elina Marinho、M. Proença

  DOI：10.1055/s-0034-1380322

  日期：2015.6

  4-(arylamino)quinazolines were prepared from 2-(acylamino)benzonitriles and primary arylamines by refluxing in either ethanol using trifluoroacetic acid as a catalyst or acetic acid. The 2-aminobenzonitrile was acylated by reaction with anhydrides, isocyanates, or ethyl chloroformate at room temperature. 2-Substituted 4-(arylamino)quinazolines were prepared from 2-(acylamino)benzonitriles and primary arylamines

  摘要 由2-（酰基氨基）苯甲腈和伯芳基胺通过在乙醇中使用三氟乙酸作为催化剂或回流进行回流来制备2-取代的4-（芳基氨基）喹唑啉。通过在室温下与酸酐，异氰酸酯或氯甲酸乙酯反应将2-氨基苄腈酰化。 由2-（酰基氨基）苯甲腈和伯芳基胺通过在乙醇中使用三氟乙酸作为催化剂或回流进行回流来制备2-取代的4-（芳基氨基）喹唑啉。通过在室温下与酸酐，异氰酸酯或氯甲酸乙酯反应将2-氨基苄腈酰化。
• KO^<i>t</i>Bu-Promoted Transition-Metal-Free Transamidation of Primary and Tertiary Amides with Amines
  作者：Tridev Ghosh、Snehasish Jana、Jyotirmayee Dash

  DOI：10.1021/acs.orglett.9b02306

  日期：2019.9.6

  transamidation of primary and tertiary amides with a range of aryl, heteroaryl, and aliphatic amines using potassium tert-butoxide. The reaction proceeds at room temperature under transition-metal-free conditions providing secondary amides in high yields. Moreover, reaction of cyclopropyl amine with tertiary amides proceeds with ring-opening to provide a rapid access to enamides.

  这项工作公开了使用叔丁醇钾将伯酰胺和叔酰胺与一定范围的芳基，杂芳基和脂肪族胺进行氨基转移。反应在室温下在无过渡金属的条件下进行，以高收率提供仲酰胺。此外，环丙胺与叔酰胺的反应以开环进行以提供对酰胺的快速访问。
• Reaction pathways for arylcarbamoyl radicals and the cyclization of o-substituted phenylcarbamoyl radicals
  作者：Rino Leardini、Antonio Tundo、Giuseppe Zanardi

  DOI：10.1039/p19810003164

  日期：——

  in the aromatic ring. When the aryl group is phenyl or p-chlorophenyl the following reactions on carbamoyl radicals occur: (i) loss of hydrogen with formation of aryl isocyanates, whereas the loss of carbon monoxide leads to arylamines via arylaminyl radicals; (ii) dimerization to NN′-diaryloxamides; (iii) aromatic substitution on chlorbenzene leading to N-arylbenzamides (ipso-substitution) and N-

  ñ从产生自由基-Arylcarbamoyl Ñ与二叔丁基过氧化物（BU -arylformamides吨OOBu吨）的氯苯在110℃下产生一系列取决于性质和取代基中的芳环中的位置反应。当芳基是苯基或对氯苯基时，在氨基甲酰基上发生以下反应：（i）氢损失并形成芳基异氰酸酯，而一氧化碳的损失通过芳基芳基导致芳胺；（II）二聚NN '-diaryloxamides; （iii）氯苯上的芳香取代导致N-arylbenzamides（本位3'-取代）和Ñ -arylchlorobenzamides。由叔丁醇和芳基胺捕集的异氰酸酯给予叔丁基Ñ -arylcarbamates和NN '-diarylureas。用o-取代的N-苯基甲酰胺也观察到分子内环化。实际上，N-（邻-氰基苯基）甲酰胺通过将氨基甲酰基加成到氰基上来提供靛红，而N -[（邻-苯硫基）苯基]甲酰胺通过S H i生成2-苯并噻唑酮和苯基。在