(4-bromophenyl)carbamoyl azide

• 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 azide
• 英文别名: (3E)-1-(4-bromophenyl)-3-diazourea
• 化学式: C₇H₅BrN₄O
• 分子量: 241.047
• InChiKey: FCLXUZFJDCJTFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  13
• 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：
  43.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  phenylcarbamoyl azide 在 四氯化碳 、 溴 作用下， 生成 (4-bromophenyl)carbamoyl azide
  参考文献：
  名称：

  Curtius; Burckhardt, Journal fur praktische Chemie (Leipzig 1954), 1898, vol. <2>58, p. 231

  摘要：

  DOI：

文献信息

• KI Catalyzed Nitrogenation of Aldehydes and Alcohols: Direct Synthesis of Carbamoyl Azides and Ureas
  作者：Song Song、Peng Feng、Miancheng Zou、Ning Jiao

  DOI：10.1002/cjoc.201600914

  日期：2017.6

  An efficient KI catalyzed nitrogenation of aldehydes and alcohols for the direct synthesis of carbamoyl azides and ureas via a radical process has been developed. The simple operating procedures, the readily available starting materials including aldehydes, alcohols and amines, as well as the utility of the products all make this strategy very attractive.

  已开发出一种有效的KI催化醛和醇的氮化，用于通过自由基过程直接合成氨基甲酰基叠氮化物和脲。简单的操作程序，易于获得的起始原料（包括醛，醇和胺）以及产品的实用性，都使该策略非常有吸引力。
• Ceric Ammonium Nitrate (CAN) Catalyzed Modification of Ketones <i>via</i> Two C–C Bond Cleavages with the Retention of the Oxo-Group
  作者：Peng Feng、Xiang Sun、Yijin Su、Xinyao Li、Li−He Zhang、Xiaodong Shi、Ning Jiao

  DOI：10.1021/ol5014476

  日期：2014.6.20

  functionalization of ketones through double C–C bond cleavage strategy has been disclosed. This reaction provides a mild, practical method toward carbamoyl azides, which are versatile intermediates and building blocks in organic synthesis. Based on relevant mechanistic studies, a unique and plausible C–C bond and N–O bond cleavage process is proposed, where the oxyamination intermediate plays an important

  已经公开了一种简单的硝酸铈铵（CAN）通过双C-C键裂解策略催化酮的官能化的方法。该反应为氨基甲酰叠氮化物提供了温和，实用的方法，氨基甲酰叠氮化物是有机合成中的通用中间体和结构单元。基于相关的机理研究，提出了一个独特且可行的C–C键和N–O键裂解过程，其中氧化胺化中间体在该反应中起着重要的作用。
• Copper-Catalyzed Nitrogenation of Aromatic and Aliphatic Aldehydes: A Direct Route to Carbamoyl Azides
  作者：Rongbiao Wei、Liang Ge、Hongli Bao、Saihu Liao、Yajun Li

  DOI：10.1055/s-0039-1690683

  日期：2019.12

  efficient copper-catalyzed synthesis of carbamoyl azides directly from aldehydes has been developed. Both aromatic aldehydes and aliphatic aldehydes, together with other commercially available reactants, can be used as substrates in this radical relay reaction. Broad substrate scope, simple operation, readily available reagents, and good functionality tolerance make this method very attractive.

  已经开发了直接由醛有效地铜催化合成氨基甲酰基叠氮化物的方法。芳族醛和脂族醛，以及其他可商购的反应物，都可以用作该自由基中继反应中的底物。广泛的底物范围，简单的操作，易于获得的试剂以及良好的功能耐受性使该方法非常有吸引力。
• One-Pot Synthesis of Carbamoyl Azides via Palladium-Catalysed Azidocarbonylation of Haloarenes Using N-Formylsaccharin as a CO Surrogate
  作者：Lal Yadav、Vinod Yadav、Vishnu Srivastava

  DOI：10.1055/s-0036-1588316

  日期：——

  A highly efficient one-pot synthesis of carbamoyl azides from haloarenes and sodium azide has been developed. The protocol involves palladium-catalysed azidocarbonylation of haloarenes utilizing N -formylsaccharin as a CO source to form acyl azides, which undergo in situ Curtius rearrangement to afford the desired carbamoyl azides. N -Formylsaccharin is an easy-to-handle solid alternative to CO gas

  已经开发出一种由卤代芳烃和叠氮化钠高效一锅法合成氨基甲酰基叠氮化物的方法。该协议涉及钯催化的卤代芳烃的叠氮羰基化，利用 N-甲酰基糖精作为 CO 源形成酰基叠氮化物，其进行原位 Curtius 重排以提供所需的氨基甲酰基叠氮化物。N-甲酰基糖精是一种易于处理的固体替代 CO 气体。
• Controlling hazardous chemicals in microreactors: Synthesis with iodine azide
  作者：Johan C Brandt、Thomas Wirth

  DOI：10.3762/bjoc.5.30

  日期：——

  Aromatic aldehydes have been converted into the corresponding carbamoyl azides using iodine azide. These reactions have been performed safely under continuous flow reaction conditions in microreactors.

  芳香醛被转化为相应的氨基甲酰氮化物，使用碘化氮。这些反应已经在微反应器中安全地进行了连续流反应条件下的实验。