4-benzoylaminobenzyl acetate | 871503-58-1

• 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-benzoylaminobenzyl acetate
• 英文别名: 4-benzamidobenzyl acetate；(4-Benzamidophenyl)methyl acetate
• CAS: 871503-58-1
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: HUQFPSYXQZFUJK-UHFFFAOYSA-N

物化性质

• 沸点：
  332.0±25.0 °C(Predicted)
• 密度：
  1.217±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-azidobenzyl acetate 、 potassium benzeneselenocarboxylate 以 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 2.0h， 以70%的产率得到4-benzoylaminobenzyl acetate
  参考文献：
  名称：

  Amide bond formation from selenocarboxylates and aromatic azides

  摘要：

  A new method of amide bond formation was developed through the reaction of potassium selenocarboxylates with aromatic azides at room temperature. Potassium selenocarboxylates were prepared in situ by the treatment of diacyl selenides with potassium methoxide at 5 degrees C under N-2. After the addition of azide, the reaction was allowed to gradually warm to room temperature and was stirred for 0.5-2 h. Excellent yields were obtained when electron deficient aromatic azides were used. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.145

文献信息

• Efficient Amidation from Carboxylic Acids and Azides via Selenocarboxylates:  Application to the Coupling of Amino Acids and Peptides with Azides
  作者：Xinghua Wu、Longqin Hu

  DOI：10.1021/jo061703n

  日期：2007.2.1

  A facile one-pot procedure for the coupling of carboxylic acid and azide via selenocarboxylate and selenatriazoline has been developed and successfully applied to the coupling of amino acids and peptides with azides. Selenocarboxylates are readily prepared by the reaction of the activated carboxylic acids with LiAlHSeH under mild conditions. The selenocarboxylates formed in situ are used to react directly

  已经开发了一种简单的一锅法，用于通过硒代羧酸盐和硒代三唑啉偶联羧酸和叠氮化物，并将其成功地用于氨基酸和肽与叠氮化物的偶联。通过在温和条件下使活化的羧酸与LiAlHSeH反应，可以轻松制备硒代羧酸盐。原位形成的硒羧酸盐用于通过硒代三唑啉中间体与叠氮化物直接反应形成相应的酰胺。对于缺乏电子的叠氮化物，获得了优异的产率，对于富含电子的叠氮化物，获得了中等至良好的产率。硒代羧酸酯/叠氮化物酰胺化反应是清洁的和化学选择性的。
• Improved solubility and stability of trialkylammonium selenocarboxylate in organic solvents for efficient amidation with azides
  作者：Prathima Surabhi、Xinghua Wu、Longqin Hu

  DOI：10.1016/j.tetlet.2006.04.144

  日期：2006.7

  Trialkylammonium selenocarboxylate, formed in situ from the reaction of diacyl diselenide with piperidine in the presence of diisopropylethylamine, was found to react readily Lit room temperature with electron-deficient azides to form amides in excellent yields. The trialkylammonium selenocarboxylate salt formed has good solubility and stability in organic solvents. The enhanced stability allowed mild heating to improve the amidation yields wish electron-rich azides. (c) 2006 Elsevier Ltd. All rights reserved.
• Amide bond formation from selenocarboxylates and aromatic azides
  作者：Xinghua Wu、Longqin Hu

  DOI：10.1016/j.tetlet.2005.09.145

  日期：2005.11

  A new method of amide bond formation was developed through the reaction of potassium selenocarboxylates with aromatic azides at room temperature. Potassium selenocarboxylates were prepared in situ by the treatment of diacyl selenides with potassium methoxide at 5 degrees C under N-2. After the addition of azide, the reaction was allowed to gradually warm to room temperature and was stirred for 0.5-2 h. Excellent yields were obtained when electron deficient aromatic azides were used. (c) 2005 Elsevier Ltd. All rights reserved.