N-chloro-N-propoxybenzamide

• 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-chloro-N-propoxybenzamide
• 英文别名: N-(3-chloropropoxy)benzamide
• 化学式: C₁₀H₁₂ClNO₂
• 分子量: 213.664
• InChiKey: NBMQAEFZVPGGEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  potassium benzohydroxamate 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 N-chloro-N-propoxybenzamide
  参考文献：
  名称：

  Mutagenicity of electrophilic N-acyloxy-N-alkoxyamides

  摘要：

  N-acyloxy-N-alkoxybenzamides are mutagenic in TA100 without the need for metabolic activation with S9, Electronic effects of substituents on both the benzamide ring in N-acetoxy-N-butoxybenzamides or the benzyloxy ring in N-acetoxy-N-benzyloxybenzamides do not influence mutagenicity levels. For N-benzoyloxy-N-benzyloxybenzamides, mutagenicity levels are inversely related to the electron-withdrawing effect of substituents on the benzoyloxy leaving group. Since reactivities increase with increasing electron-withdrawing effects, mutagenicity correlates with stability rather than reactivity of these mutagens. Hydrophobicity is the dominant factor controlling mutagenicity levels and data for all mutagens correlate with computed log P values with a lower dependence (h = 0.22) than that recorded for indirect mutagens (h = 1.0), except where a sterically demanding p-tert-butyl substituent or a naphthyl group is present. N-acetoxy-N-butoxynaphthamide exhibits a much higher level of mutagenicity than predicted by its log P value and activity may be ascribed to an intercalative binding process with DNA rather than straightforward hydrophobic binding in the major or minor groove. Since these are direct-acting mutagens, structural factors influence binding and reactivity towards DNA. (C) 2001 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s1383-5718(01)00189-9

文献信息

• Mutagenicity of electrophilic N-acyloxy-N-alkoxyamides
  作者：Antonio M Bonin、Tony M Banks、John J Campbell、Stephen A Glover、Gerard P Hammond、Arungundrum S Prakash、Colleen A Rowbottom

  DOI：10.1016/s1383-5718(01)00189-9

  日期：2001.7

  N-acyloxy-N-alkoxybenzamides are mutagenic in TA100 without the need for metabolic activation with S9, Electronic effects of substituents on both the benzamide ring in N-acetoxy-N-butoxybenzamides or the benzyloxy ring in N-acetoxy-N-benzyloxybenzamides do not influence mutagenicity levels. For N-benzoyloxy-N-benzyloxybenzamides, mutagenicity levels are inversely related to the electron-withdrawing effect of substituents on the benzoyloxy leaving group. Since reactivities increase with increasing electron-withdrawing effects, mutagenicity correlates with stability rather than reactivity of these mutagens. Hydrophobicity is the dominant factor controlling mutagenicity levels and data for all mutagens correlate with computed log P values with a lower dependence (h = 0.22) than that recorded for indirect mutagens (h = 1.0), except where a sterically demanding p-tert-butyl substituent or a naphthyl group is present. N-acetoxy-N-butoxynaphthamide exhibits a much higher level of mutagenicity than predicted by its log P value and activity may be ascribed to an intercalative binding process with DNA rather than straightforward hydrophobic binding in the major or minor groove. Since these are direct-acting mutagens, structural factors influence binding and reactivity towards DNA. (C) 2001 Elsevier Science B.V. All rights reserved.