crotonoyl azide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: crotonoyl azide
• 英文别名: 1-azidobut-2-en-1-one；N-crotonoyl azide；α-crotonic acid azide；α-Crotonsaeureazid；But-2-enoyl azide；but-2-enoyl azide
• 化学式: C₄H₅N₃O
• 分子量: 111.103
• InChiKey: NXUSZMKDZBGZRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  crotonoyl azide 生成 异氰酸丙烯酯
  参考文献：
  名称：

  Iwakura; Suzuki, Nippon Kagaku Zasshi, 1956, vol. 77, p. 64,65

  摘要：

  DOI：
• 作为产物：
  描述：

  巴豆酸 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 crotonoyl azide
  参考文献：
  名称：

  串联手性磷酸铜（II）催化硝基还原脱氧/对映选择性Povarov与烯草胺的反应

  摘要：

  切割并连接在一起：手性磷酸铜配合物有效地促进了脱氧/ [4 + 2]环加成反应的串联序列。此过程可通过三个连续的立体异构中心以良好的非对映和对映选择性获得高产率的各种四氢喹啉。

  DOI：

  10.1002/ejoc.201900547

文献信息

• Tandem Chiral Cu(II) Phosphate‐Catalyzed Deoxygenation of Nitrones/Enantioselective Povarov Reaction with Enecarbamates
  作者：Coralie Gelis、Guillaume Levitre、Vincent Guérineau、David Touboul、Luc Neuville、Géraldine Masson

  DOI：10.1002/ejoc.201900547

  日期：2019.9

  Cut and join together: Chiral Copper phosphate complexes efficiently promoted a tandem sequence of deoxygenation/[4+2] cycloaddition reactions. This process gives access to various tetrahydroquinolines with three consecutive stereogenic centers in good yields with excellent diastereo‐and enantioselectivity.

  切割并连接在一起：手性磷酸铜配合物有效地促进了脱氧/ [4 + 2]环加成反应的串联序列。此过程可通过三个连续的立体异构中心以良好的非对映和对映选择性获得高产率的各种四氢喹啉。
• Trapping of Isocyanates with Benzotriazole in situ - Preparation of Carbamoyl Benzotriazoles as an Isocyanate Alternative via Curtius Rearrangement
  作者：Xiaoxia Wang、Zhiyun Zhong、Lichun Kong、Xiangming Zhu

  DOI：10.1055/s-0029-1217820

  日期：2009.9

  N-Aryl and N-alkenyl carbamoyl benzotriazoles were prepared in good to excellent yields from acyl azides and benzotri-azole via Curtius rearrangement, while N-alkylcarbamoyl benzotriazoles were formed from N-alkanoyl benzotriazoles and sodium azide in one pot. The carbamoyl benzotriazoles can be used as a stable isocyanate alternative, as has been demonstrated by its reaction with amines to synthesize

  N-芳基和N-烯基氨基甲酰基苯并三唑通过Curtius重排从酰基叠氮化物和苯并三唑以良好到优异的产率制备，而N-烷基氨基甲酰基苯并三唑由N-烷酰基苯并三唑和叠氮化钠在一锅中形成。氨基甲酰基苯并三唑可用作稳定的异氰酸酯替代物，正如其与胺反应以优异的产率合成脲所证明的那样。
• Photoredox-Induced Three-Component Oxy-, Amino-, and Carbotrifluoromethylation of Enecarbamates
  作者：Aude Carboni、Guillaume Dagousset、Emmanuel Magnier、Géraldine Masson

  DOI：10.1021/ol500374e

  日期：2014.2.21

  A photoredox-catalzyed trifluoromethylation of enecarbamates process is reported. This pathway uses Togni's reagent as the CF3 source and follows a radical/cationic pathway. Under the optimized conditions using [Ru(bpy)(3)(PF6)(2)] as the photocatalyst, a wide range of substituted enecarbamates can readily be difunctionalized by means of various O, N, and C nudeophiles.
• FeCl₃ · 6H₂O-Catalyzed Acceleration of the Acylation of Sodium Azide with<i>N</i>-Acylbenzotriazoles
  作者：Zhiyun Zhong、Jieling Hu、Xiaoxia Wang、Junhua Liu、Longfeng Zhang

  DOI：10.1080/00397911.2010.505698

  日期：2011.8.15

  [image omitted] Catalyzed by ferric chloride hexahydrate (FeCl3 center dot 6H2O), the acylation of sodium azide with N-acylbenzotriazoles was greatly accelerated in a mixed solvent of acetone and water. Thus, good to excellent yields of a variety of acyl azides were obtained at room temperature in a short time. Furthermore, because of the complete conversion of N-acylbenzotriazoles and the easy removal of the by-product, purification by column chromatography was no longer required, which made the protocol suitable for large-scale preparation.
• Jones; Mason, Journal of the American Chemical Society, 1927, vol. 49, p. 2533
  作者：Jones、Mason

  DOI：——

  日期：——