(4-bromophenyl)carbamoyl cyanide | 73708-67-5

• 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: (4-bromophenyl)carbamoyl cyanide
• 英文别名: N-(4-Bromophenyl)cyanoformamide；N-(4-bromophenyl)-1-cyanoformamide
• CAS: 73708-67-5
• 化学式: C₈H₅BrN₂O
• 分子量: 225.044
• InChiKey: OFDVDYICRIKOTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 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

• 作为产物：
  描述：

  α-Oximino-acetessigsaeure-p-bromanilid 在 2,2-dichloro-1,3-dicyclohexylimidazolidine-4,5-dione 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以96%的产率得到(4-bromophenyl)carbamoyl cyanide
  参考文献：
  名称：

  4,5-Dioxo-imidazolinium Cation Activation of 1-Acyl-1-carbamoyl Oximes: Access to Cyanoformamides Using Dichloroimidazolidinedione

  摘要：

  Cyanoformamides are prevalent as versatile building blocks for accessing synthetically useful intermediates and biologically active compounds. The development of a milder, simpler, and more efficient approach to cyanoformamides is nontrivial. Herein, we demonstrate the effectiveness of 4,S-dioxo-imidazolinium cation activation for transforming 1-aryl-1-carbamoyl oximes to cyanoformamides. By making use of the readily available and highly modifiable dichloroimidazolidinediones (DCIDs), this novel method of activation offers reactivity remarkably greater than that of other reported protocols, exhibits a high functional group compatibility with mild conditions, and could be scaled up easily. More than 30 examples are demonstrated with good to excellent yields in short reaction times. This research not only provides a mild and efficient alternative approach to assembling a portfolio of cyanoformamides but also extends the dichloroimidazolidinedione-mediated chemistry to encompass the C-C bond cleavage reaction.

  DOI：

  10.1021/acs.joc.9b02992

文献信息

• Iodine-DMSO mediated conversion of <i>N</i>-arylcyanothioformamides to <i>N</i>-arylcyanoformamides and the unexpected formation of 2-cyanobenzothiazoles
  作者：Ziad Moussa、Zaher M. A. Judeh、Ahmed Alzamly、Saleh A. Ahmed、Harbi Tomah Al-Masri、Bassam Al-Hindawi、Faisal Rasool、Sara Saada

  DOI：10.1039/d2ra00049k

  日期：——

  substrates to access new luciferin analogs. The structures of all new products were elucidated by multinuclear NMR spectroscopy and high accuracy mass spectral analysis. Crystal-structure determination by means of single-crystal X-ray diffraction was carried out on (4-bromophenyl)carbamoyl cyanide, 5,6-dimethoxybenzo[d]thiazole-2-carbonitrile, 5-(benzyloxy)benzo[d]oxazole-2-carbonitrile, 4,7-dimetho

  氰基甲酰胺作为组装关键中间体和生物活性分子的有用成分无处不在。开发一种有效且简单的方法来处理这个主题是一个挑战。在此，我们证明了 I 2 -DMSO 氧化系统在从N制备N-芳基氰基甲酰胺中的有效性。-芳基氰基硫代甲酰胺。该合成方法具有条件温和、底物范围广、反应效率高等特点。此外，这种方法提供了一个很好的入口，可以专门提供 2-氰基苯并噻唑，它们是获得新荧光素类似物的有用底物。所有新产品的结构均通过多核核磁共振光谱和高精度质谱分析进行了阐明。用单晶X射线衍射对(4-溴苯基)氨基甲酰氰、5,6-二甲氧基苯并[ d ]噻唑-2-甲腈、5-(苄氧基)苯并[ d ]恶唑进行晶体结构测定-2-甲腈，4,7-二甲氧基苯并[ d]噻唑-2-甲腈和(5-碘-2,4-二甲氧基苯基)氨基甲酰氰，一种具有机理意义的关键中间体。
• 4,5-Dioxo-imidazolinium Cation Activation of 1-Acyl-1-carbamoyl Oximes: Access to Cyanoformamides Using Dichloroimidazolidinedione
  作者：Yu Gao、Zhihao Zhang、Zhenjiang Li、Tianfo Guo、Yuejia Zhu、Zhiwei Yao、Bo Liu、Yongqiang Li、Kai Guo

  DOI：10.1021/acs.joc.9b02992

  日期：2020.1.17

  Cyanoformamides are prevalent as versatile building blocks for accessing synthetically useful intermediates and biologically active compounds. The development of a milder, simpler, and more efficient approach to cyanoformamides is nontrivial. Herein, we demonstrate the effectiveness of 4,S-dioxo-imidazolinium cation activation for transforming 1-aryl-1-carbamoyl oximes to cyanoformamides. By making use of the readily available and highly modifiable dichloroimidazolidinediones (DCIDs), this novel method of activation offers reactivity remarkably greater than that of other reported protocols, exhibits a high functional group compatibility with mild conditions, and could be scaled up easily. More than 30 examples are demonstrated with good to excellent yields in short reaction times. This research not only provides a mild and efficient alternative approach to assembling a portfolio of cyanoformamides but also extends the dichloroimidazolidinedione-mediated chemistry to encompass the C-C bond cleavage reaction.