N-Cyclohexyl-2-azido-2-phenylethanamide

• 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: N-Cyclohexyl-2-azido-2-phenylethanamide
• 英文别名: 2-azido-N-cyclohexyl-2-phenylacetamide
• 化学式: C₁₄H₁₈N₄O
• 分子量: 258.323
• InChiKey: PWAQULHUSMTEBK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(mesyloxy)-N-cyclohexylphenylacetamide 在 sodium azide 、 15-冠醚-5 作用下， 以 二氯甲烷 为溶剂， 反应 100.0h， 以71%的产率得到N-Cyclohexyl-2-azido-2-phenylethanamide
  参考文献：
  名称：

  Synthesis of .alpha.-azido and .alpha.-amino amides from N-[(methylsulfonyl)oxy]amides

  摘要：

  Effective new syntheses of 2-azido amides and 2-amino amides from N-(mesyloxy) amides 1 have been developed. 2-Azido amides are produced by treating 1 with sodium azide in the presence of 15-crown-5. 2-Amino amides result from the reaction of 1 with various amines. Regiochemical control in the preparation of 2-amino amides is possible by modulating the amine nucleophilicity by steric bulk.

  DOI：

  10.1021/jo00061a004

文献信息

• New Experimental Strategies in Amide Synthesis using<i>N,N</i>-Bis[2-oxo-3-oxazolidinyl]phosphorodiamidic Chloride
  作者：Juan Cabré、Antonio Luis Palomo

  DOI：10.1055/s-1984-30857

  日期：——
• CABRE, J.;PALOMO, A. L., SYNTHESIS, BRD, 1984, N 5, 413-417
  作者：CABRE, J.、PALOMO, A. L.

  DOI：——

  日期：——
• Synthesis of .alpha.-azido and .alpha.-amino amides from N-[(methylsulfonyl)oxy]amides
  作者：Robert V. Hoffman、Naresh K. Nayyar、Wenting Chen

  DOI：10.1021/jo00061a004

  日期：1993.4

  Effective new syntheses of 2-azido amides and 2-amino amides from N-(mesyloxy) amides 1 have been developed. 2-Azido amides are produced by treating 1 with sodium azide in the presence of 15-crown-5. 2-Amino amides result from the reaction of 1 with various amines. Regiochemical control in the preparation of 2-amino amides is possible by modulating the amine nucleophilicity by steric bulk.