N-benzoyloxy-N-(p-tert-butylbenzyloxy)-p-tert-butylbenzamide | 693809-14-2

• 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-benzoyloxy-N-(p-tert-butylbenzyloxy)-p-tert-butylbenzamide
• 英文别名: [(4-Tert-butylbenzoyl)-[(4-tert-butylphenyl)methoxy]amino] benzoate
• CAS: 693809-14-2
• 化学式: C₂₉H₃₃NO₄
• 分子量: 459.585
• InChiKey: RZXPVDWJLFMWCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  sodium benzoate 、 N-(4-tert-butylbenzyloxy)-N-chloro-4-tert-butylbenzamide 以 丙酮 为溶剂， 以84%的产率得到N-benzoyloxy-N-(p-tert-butylbenzyloxy)-p-tert-butylbenzamide
  参考文献：
  名称：

  The role of steric effects in the direct mutagenicity of N-acyloxy-N-alkoxyamides

  摘要：

  Electrophilic N-acyloxy-N-alkoxyamides are mutagenic in Salmonella typhimurium TA100 without the need for S9 metabolic activation and they react with DNA at guanine-N7 at physiological pH. Since these are direct-acting mutagens, structural factors influence binding and reactivity with DNA. Mutagenicity in TA100 can be predicted by a QSAR incorporating hydrophobicity (log P), stability to substitution reactions at nitrogen (pK(a) of the leaving acid) and steric effects of para-aryl substituents (E-s). A number of mutagens exhibit activities that deviate markedly from the predicted values and they fall into two classes: di-tert-butylated N-benzoyloxy-N-benzyloxybenzamides, which - because of their size - are most probably excluded from the major groove or are unable to achieve a transition state for reaction with DNA, and N-benzoyloxy-N-butoxyalkylamides with branching a-to the amide carbonyl, which are resistant to S(N)2 reactions at the amide nitrogen. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.mrgentox.2006.02.003

文献信息

• The role of steric effects in the direct mutagenicity of N-acyloxy-N-alkoxyamides
  作者：Luke E. Andrews、Antonio M. Bonin、Linda E. Fransson、Ashley-Mae E. Gillson、Stephen A. Glover

  DOI：10.1016/j.mrgentox.2006.02.003

  日期：2006.6

  Electrophilic N-acyloxy-N-alkoxyamides are mutagenic in Salmonella typhimurium TA100 without the need for S9 metabolic activation and they react with DNA at guanine-N7 at physiological pH. Since these are direct-acting mutagens, structural factors influence binding and reactivity with DNA. Mutagenicity in TA100 can be predicted by a QSAR incorporating hydrophobicity (log P), stability to substitution reactions at nitrogen (pK(a) of the leaving acid) and steric effects of para-aryl substituents (E-s). A number of mutagens exhibit activities that deviate markedly from the predicted values and they fall into two classes: di-tert-butylated N-benzoyloxy-N-benzyloxybenzamides, which - because of their size - are most probably excluded from the major groove or are unable to achieve a transition state for reaction with DNA, and N-benzoyloxy-N-butoxyalkylamides with branching a-to the amide carbonyl, which are resistant to S(N)2 reactions at the amide nitrogen. (c) 2006 Elsevier B.V. All rights reserved.