N-(1-benzotriazol-1-yl-2-phenylethyl)-3-pyridinecarboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: N-(1-benzotriazol-1-yl-2-phenylethyl)-3-pyridinecarboxamide
• 英文别名: N-[1-(benzotriazol-1-yl)-2-phenylethyl]pyridine-3-carboxamide
• 化学式: C₂₀H₁₇N₅O
• 分子量: 343.388
• InChiKey: BKONJWIMITUQAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  72.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(1-benzotriazol-1-yl-2-phenylethyl)-3-pyridinecarboxamide 在 三氟甲磺酸三甲基硅酯 、 sodium hydride 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 mineral oil 为溶剂， 生成 5-phenyl-2-(pyridin-3-yl)oxazole
  参考文献：
  名称：

  Iodine(III)-Promoted Synthesis of Oxazoles through Oxidative Cyclization of N-Styrylbenzamides

  摘要：

  The hypervalent iodine reagent PhI(OTf)(2), generated in situ, has been successfully utilized in an intramolecular oxidative cyclization of N-styrylbenzamides. In remarkably short reaction times, the desired 2,5-disubstituted oxazoles were isolated in high yields in this metal-free oxidative C-O bond-forming reaction.

  DOI：

  10.1055/s-0033-1339491
• 作为产物：
  描述：

  T406石油添加剂 、 烟酰胺 、 苯乙醛 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以33%的产率得到N-(1-benzotriazol-1-yl-2-phenylethyl)-3-pyridinecarboxamide
  参考文献：
  名称：

  A Novel Route to N-Styrylamides

  摘要：

  A general synthesis of N-styrylamides starting from amides and phenylacetaldehyde is described. Condensation of the amide, aldehyde and benzotriazole affords N-(1-benzotriazol-1-yl-2-phenylethyl)amides 2 from which the benzotriazole molecule is smoothly eliminated.

  DOI：

  10.1080/00397919508012683

文献信息

• A Novel Route to N-Styrylamides
  作者：A. R. Katritzky、A. V. Ignatchenko、H. Lang

  DOI：10.1080/00397919508012683

  日期：1995.4

  A general synthesis of N-styrylamides starting from amides and phenylacetaldehyde is described. Condensation of the amide, aldehyde and benzotriazole affords N-(1-benzotriazol-1-yl-2-phenylethyl)amides 2 from which the benzotriazole molecule is smoothly eliminated.
• Katritzky Alan R., Ignatchenko Alexey V., Lang Hengyuan, Synth. Commun, 25 (1995) N 8, S 1197-1204
  作者：Katritzky Alan R., Ignatchenko Alexey V., Lang Hengyuan

  DOI：——

  日期：——
• Iodine(III)-Promoted Synthesis of Oxazoles through Oxidative Cyclization of N-Styrylbenzamides
  作者：Boris Nachtsheim、Christian Hempel

  DOI：10.1055/s-0033-1339491

  日期：——

  The hypervalent iodine reagent PhI(OTf)(2), generated in situ, has been successfully utilized in an intramolecular oxidative cyclization of N-styrylbenzamides. In remarkably short reaction times, the desired 2,5-disubstituted oxazoles were isolated in high yields in this metal-free oxidative C-O bond-forming reaction.