2-benzamido-N-(4-methoxybenzyl)benzamide

• 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: 2-benzamido-N-(4-methoxybenzyl)benzamide
• 英文别名: 2-benzamido-N-[(3-methoxyphenyl)methyl]benzamide
• 化学式: C₂₂H₂₀N₂O₃
• 分子量: 360.412
• InChiKey: ANBKLBDODFTCRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzamido-N-(4-methoxybenzyl)benzamide 在 碘 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以96%的产率得到3-(4-methoxybenzyl)-2-phenylquinazolin-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：

  2-amino-N-(4-methoxybenzyl)benzamide 、 苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以90%的产率得到2-benzamido-N-(4-methoxybenzyl)benzamide
  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

文献信息

• Hexamethyldisilazane-iodine induced intramolecular dehydrative cyclization of diamides: a general access to natural and unnatural quinazolinones
  作者：Umesh A. Kshirsagar、Santosh B. Mhaske、Narshinha P. Argade

  DOI：10.1016/j.tetlet.2007.03.032

  日期：2007.4

  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.