4-(dimethylamino)-N-(2-phenylethyl)benzamide | 108191-14-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(dimethylamino)-N-(2-phenylethyl)benzamide
• CAS: 108191-14-6
• 化学式: C₁₇H₂₀N₂O
• 分子量: 268.359
• InChiKey: WMHYEJIIJRBJGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-[4-(dimethylamino)phenyl]-N-(2-phenylethyl)methanimine oxide 在 磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 以88%的产率得到4-(dimethylamino)-N-(2-phenylethyl)benzamide
  参考文献：
  名称：

  Unexpected Reaction Of A-Aryl-N-(P-Phenylethyl) Nitrones With Chlorinating Agents

  摘要：

  The alpha-aryl-N-(beta-phenylethyl)nitrones when subjected to SO2Cl2/Et3N and NCS/NaOMe treatment independently, gave unexpectedly the corresponding amides. These procedures form an alternative route for the rearrangement of nitrones to amides.

  DOI：

  10.1080/00397919908086190

文献信息

• Synthesis and anticonvulsant activity of analogs of 4-amino-N-(1-phenylethyl)benzamide
  作者：C. Randall Clark、Timothy W. Davenport

  DOI：10.1021/jm00390a016

  日期：1987.7

  to 4-amino-N-(1-phenylethyl)benzamide, 1, were prepared in a study on the relationship of structure to anticonvulsant activity in this compound. Acylation and alkylation of the amino group of 1 resulted in almost total loss of anticonvulsant activity. Insertion of a methylene between the 4-amino group and the aromatic ring of 1 produced a slight increase in anticonvulsant potency and a significant increase

  为了研究该化合物的结构与抗惊厥活性之间的关系，制备了一组与4-氨基-N-（1-苯基乙基）苯甲酰胺有关的酰胺和胺。1氨基的酰化和烷基化导致抗惊厥活性几乎完全丧失。在4-氨基和1的芳环之间插入亚甲基会导致抗惊厥药力的轻微增加和毒性的显着增加。1中酰胺羰基的氢化物还原还产生具有抗电击引起的惊厥的ED50稍低的化合物，而在转子法中的TD50则低得多。1-苯基乙基1的修饰也降低了抗惊厥药的效力。
• The use of microwave radiations and propylphosphonic anhydride (T3P®) for rapid and highly yielding amide bond formation and peptide coupling
  作者：Elisa Rouge、Jean Michel Brunel

  DOI：10.1016/j.tet.2023.133813

  日期：2024.1

  An improved, fast, and efficient procedure for amide bond formation and peptide coupling is reported leading to the expected corresponding derivatives in good to excellent isolated yields ranging from 26 to 90%. The outcome of the reaction was also investigated in relation to the influence of different parameters such as the nature of the solvent, the temperature as well as the amine/carboxylic acid

  据报道，一种改进的、快速且有效的酰胺键形成和肽偶联程序可产生预期的相应衍生物，其分离产率范围为 26% 至 90%，从良好到优异。还研究了反应结果与不同参数的影响，例如溶剂的性质、温度以及涉及的胺/羧酸对或水解条件。
• CLARK C. R.; DAVENPORT T. W., J. MED. CHEM., 30,(1987) N 7, 1214-1218
  作者：CLARK C. R.、 DAVENPORT T. W.

  DOI：——

  日期：——
• Unexpected Reaction Of A-Aryl-N-(P-Phenylethyl) Nitrones With Chlorinating Agents
  作者：Ponnusamy Mohan、Arumugasamy Vanangamudi、Muniappan Thirumalaikumar、Shanmugam Muthusubramanian、Shunmugaperumal Sivasubramanian

  DOI：10.1080/00397919908086190

  日期：1999.6

  The alpha-aryl-N-(beta-phenylethyl)nitrones when subjected to SO2Cl2/Et3N and NCS/NaOMe treatment independently, gave unexpectedly the corresponding amides. These procedures form an alternative route for the rearrangement of nitrones to amides.