2-Oximino-N-benzylacetacetamide | 77335-87-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-Oximino-N-benzylacetacetamide
• 英文别名: 2-(hydroxyimino)-3-oxo-N-benzylbutanamide；N-benzyl-2-hydroxyimino-3-oxobutanamide
• CAS: 77335-87-6
• 化学式: C₁₁H₁₂N₂O₃
• 分子量: 220.228
• InChiKey: BJWSFOYDUYUSMM-UHFFFAOYSA-N

物化性质

• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.72
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  78.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-Oximino-N-benzylacetacetamide 在 三氯氧磷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以89%的产率得到benzylcarbamoyl cyanide
  参考文献：
  名称：

  POCl 3介导的1-酰基-1-氨基甲酰基肟的反应：氰甲酰胺的新入口。

  摘要：

  cyanoformamides的一种简便，高效的一锅合成从由phosphoryltrichloride介导的容易获得的1-酰基-1-氨基甲酰基肟（三氯氧磷开发3处于良好的产量高温和的条件下）。

  DOI：

  10.1021/ol503643p
• 作为产物：
  描述：

  乙酰乙酰苄胺（AABA） 在 sodium nitrite 作用下， 以 溶剂黄146 为溶剂， 以82%的产率得到2-Oximino-N-benzylacetacetamide
  参考文献：
  名称：

  Veronese, A.C.; Cavicchioni, G.; Servadio, G., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 1723 - 1725

  摘要：

  DOI：

文献信息

• POCl₃-Mediated Reaction of 1-Acyl-1-carbamoyl Oximes: A New Entry to Cyanoformamides
  作者：Jiming Yang、Dexuan Xiang、Rui Zhang、Ning Zhang、Yongjiu Liang、Dewen Dong

  DOI：10.1021/ol503643p

  日期：2015.2.20

  A facile and efficient one-pot synthesis of cyanoformamides was developed from readily available 1-acyl-1-carbamoyl oximes mediated by phosphoryltrichloride (POCl3) under mild conditions in good to high yields.

  cyanoformamides的一种简便，高效的一锅合成从由phosphoryltrichloride介导的容易获得的1-酰基-1-氨基甲酰基肟（三氯氧磷开发3处于良好的产量高温和的条件下）。
• One-Pot Synthesis of 2-Vinylimidazole Derivatives by Reaction of α-Hydroxyimino-β-dicarbonyl Compounds with Allylamine
  作者：A. C. Veronese、G. Vecchiati、S. Sferra、P. Orlandini

  DOI：10.1055/s-1985-31186

  日期：——
• Veronese, A.C.; Cavicchioni, G.; Servadio, G., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 1723 - 1725
  作者：Veronese, A.C.、Cavicchioni, G.、Servadio, G.、Vecchiati, G.

  DOI：——

  日期：——
• 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.