N-(benzyloxy)-N-((4-(tert-butyl)benzoyl)oxy)benzamide | 220168-56-9

• 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: N-(benzyloxy)-N-((4-(tert-butyl)benzoyl)oxy)benzamide
• 英文别名: benzyl N-(4-tert-butylbenzoyloxy)benzohydroxamate；N-benzyloxy-N-(4-tert-butylbenzoyloxy)benzamide；Benzamide, N-((4-(1,1-dimethylethyl)benzoyl)oxy)-N-(phenylmethoxy)-；[benzoyl(phenylmethoxy)amino] 4-tert-butylbenzoate
• CAS: 220168-56-9
• 化学式: C₂₅H₂₅NO₄
• 分子量: 403.478
• InChiKey: CXRJSEQFRPDABN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-甲基苯胺 、 N-(benzyloxy)-N-((4-(tert-butyl)benzoyl)oxy)benzamide 以 氘代甲醇 为溶剂， 生成 苯甲酸苄酯 、 对叔丁基苯甲酸 、 1,4-dimethyl-1,4-diphenyl-2-tetrazine
  参考文献：
  名称：

  Campbell, John J.; Glover, Stephen A., Journal of Chemical Research, Miniprint, 1999, # 8, p. 2075 - 2096

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(苯基甲氧基)苯甲酰胺 在 次氯酸叔丁酯 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 5.0h， 生成 N-(benzyloxy)-N-((4-(tert-butyl)benzoyl)oxy)benzamide
  参考文献：
  名称：

  A Comparison of the Reactivity and Mutagenicity of N-(Benzoyloxy)-N-(benzyloxy)benzamides

  摘要：

  A new series of N-(acyloxy)-N-alkoxybenzamides, N-(benzoyloxy) -N-(benzyloxy)benzamides 7 have been synthesized and have been found to be direct acting mutagens in Salmonella TA100. They undergo A(Al)1 solvolysis to give N-benzoyl-N-(benzyloxy)nitrenium ions 3 under conditions of acid catalysis as well as unusual B(Al)2 reactions at nitrogen with hydroxide. The latter process affords as intermediates the anomeric hydroxamic esters 4 which rearrange intramolecularly to esters in a HERON reaction. Rates of acid-catalyzed solvolysis and reaction with hydroxide ions correlate with Hammett a values with low sensitivity (rho = +0.32 and +0.55, respectively) in accordance with the A(Al)1 and B(Al)2 mechanisms. Mutagenicity for the series also appears to correlate with Hammett sigma values but with low, negative sensitivity (rho = -0.57), and their biological activity may be attributable to their stability under conditions of the Ames assay and hydrophobic binding to DNA, rather than their chemical reactivity.

  DOI：

  10.1021/jo980863z

文献信息

• A Comparison of the Reactivity and Mutagenicity of <i>N</i>-(Benzoyloxy)-<i>N</i>-(benzyloxy)benzamides
  作者：Stephen A. Glover、Gerard P. Hammond、Antonio M. Bonin

  DOI：10.1021/jo980863z

  日期：1998.12.1

  A new series of N-(acyloxy)-N-alkoxybenzamides, N-(benzoyloxy) -N-(benzyloxy)benzamides 7 have been synthesized and have been found to be direct acting mutagens in Salmonella TA100. They undergo A(Al)1 solvolysis to give N-benzoyl-N-(benzyloxy)nitrenium ions 3 under conditions of acid catalysis as well as unusual B(Al)2 reactions at nitrogen with hydroxide. The latter process affords as intermediates the anomeric hydroxamic esters 4 which rearrange intramolecularly to esters in a HERON reaction. Rates of acid-catalyzed solvolysis and reaction with hydroxide ions correlate with Hammett a values with low sensitivity (rho = +0.32 and +0.55, respectively) in accordance with the A(Al)1 and B(Al)2 mechanisms. Mutagenicity for the series also appears to correlate with Hammett sigma values but with low, negative sensitivity (rho = -0.57), and their biological activity may be attributable to their stability under conditions of the Ames assay and hydrophobic binding to DNA, rather than their chemical reactivity.
• Campbell, John J.; Glover, Stephen A., Journal of Chemical Research, Miniprint, 1999, # 8, p. 2075 - 2096
  作者：Campbell, John J.、Glover, Stephen A.

  DOI：——

  日期：——