2-hydroximinoacetoacet-2-naphthylamide | 2856-48-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroximinoacetoacet-2-naphthylamide
• CAS: 2856-48-6
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: CFDICGYXMPIVOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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-hydroximinoacetoacet-2-naphthylamide 在 2,2-dichloro-1,3-dicyclohexylimidazolidine-4,5-dione 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以91%的产率得到naphthalen-2-ylcarbamoyl 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

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Ni: MVol.C2, 8.3, page 820 - 832
  作者：

  DOI：——

  日期：——
• Desai, R. M.; Patel, M. R.; Mankad, B. N., Current Science, 1964, vol. 33, p. 613 - 614
  作者：Desai, R. M.、Patel, M. R.、Mankad, B. N.

  DOI：——

  日期：——