3-propionamido-N-p-tolylbenzamide | 25628-87-9

• 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: 3-propionamido-N-p-tolylbenzamide
• 英文别名: N-Propionyl-anthranilsaeure-p-toluidid；N-(4-methylphenyl)-2-(propanoylamino)benzamide
• CAS: 25628-87-9
• 化学式: C₁₇H₁₈N₂O₂
• 分子量: 282.342
• InChiKey: CQXHRYJVXFVDEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-propionamido-N-p-tolylbenzamide 在 碘 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以93%的产率得到2-ethyl-3-p-tolylquinazolin-4(3H)-one
  参考文献：
  名称：

  Hexamethyldisilazane-iodine induced intramolecular dehydrative cyclization of diamides: a general access to natural and unnatural quinazolinones

  摘要：

  A simple and efficient general approach to various quinazolinone scaffolds, including peptidomimetic examples, has been demonstrated by employing HMDS/I-2 for the intramolecular dehydrative cyclization of diamides. The protecting groups -Boc, -Fmoc and -Cbz tolerated the present reaction conditions and we did not observe any racemization. The present protocol has also been used as a key step for the efficient four-step syntheses of the naturally occurring quinazolinones, sclerotigenin, (-)-circumdatin-F and (-)-fumiquinazoline-F. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.032
• 作为产物：
  描述：

  丙酰氯 、 2-氨基-N-对甲苯苯甲酰胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以98%的产率得到3-propionamido-N-p-tolylbenzamide
  参考文献：
  名称：

  Hexamethyldisilazane-iodine induced intramolecular dehydrative cyclization of diamides: a general access to natural and unnatural quinazolinones

  摘要：

  A simple and efficient general approach to various quinazolinone scaffolds, including peptidomimetic examples, has been demonstrated by employing HMDS/I-2 for the intramolecular dehydrative cyclization of diamides. The protecting groups -Boc, -Fmoc and -Cbz tolerated the present reaction conditions and we did not observe any racemization. The present protocol has also been used as a key step for the efficient four-step syntheses of the naturally occurring quinazolinones, sclerotigenin, (-)-circumdatin-F and (-)-fumiquinazoline-F. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.032