N-(acetoxy)-butoxy-4-chlorobenzamide | 131229-62-4

• 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-(acetoxy)-butoxy-4-chlorobenzamide
• 英文别名: N-acetoxy-N-butoxy-p-chlorobenzamide；butyl N-acetoxy-p-chlorobenzohydroxamate；Butoxy(4-chlorobenzoyl)azanyl acetate；[butoxy-(4-chlorobenzoyl)amino] acetate
• CAS: 131229-62-4
• 化学式: C₁₃H₁₆ClNO₄
• 分子量: 285.727
• InChiKey: YLNHLARXJIFUJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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-(acetoxy)-butoxy-4-chlorobenzamide 在 sodium hydroxide 、 (苯甲酰基-(苯基甲氧基)氨基)乙酸酯 作用下， 以 乙腈 为溶剂， 以46.3%的产率得到4-氯苯甲酸丁酯
  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
• 作为产物：
  描述：

  4-氯苯甲酸乙酯 在 氢氧化钾 、 次氯酸叔丁酯 、 盐酸羟胺 、 sodium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 N-(acetoxy)-butoxy-4-chlorobenzamide
  参考文献：
  名称：

  Campbell, John J.; Glover, Stephen A.; Hammond, Gerard P., Journal of the Chemical Society. Perkin transactions II, 1991, # 12, p. 2067 - 2080

  摘要：

  DOI：
• 作为试剂：
  描述：

  (苯甲酰基-(苯基甲氧基)氨基)乙酸酯 在 sodium hydroxide 、 N-(acetoxy)-butoxy-4-chlorobenzamide 作用下， 以 乙腈 为溶剂， 以43.3%的产率得到苯甲酸苄酯
  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

• Solvolysis and mutagenesis of n-acetoxy-n-alkoxybenzamides — evidence for nitrenium ion formation
  作者：John J. Campbell、Stephen A. Glover、Colleen A. Rowbottom

  DOI：10.1016/s0040-4039(00)98076-6

  日期：——

  Mutagenic N-acetoxy-N-butoxybenzamides undergo acid catalysed solvolysis in acetonitrile/water. Kinetic data and a Hammett σ+ correlation (ϱ=−1.4) indicate nitrenium ion formation in the rate determining step. Levels of mutagenicity mirror the rates of solvolysis suggesting nitrenium ion involvement.

  致突变的N-乙酰氧基-N-丁氧基苯甲酰胺在乙腈/水中经历酸催化的溶剂分解。动力学数据和Hammettσ +相关性（ϱ = -1.4）表示速率确定步骤中形成了氮离子。致突变性水平反映了溶剂分解的速率，暗示了氮离子的参与。
• 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：——
• Campbell, John J.; Glover, Stephen A., Journal of the Chemical Society. Perkin transactions II, 1992, # 10, p. 1661 - 1663
  作者：Campbell, John J.、Glover, Stephen A.

  DOI：——

  日期：——
• Campbell, John J.; Glover, Stephen A.; Hammond, Gerard P., Journal of the Chemical Society. Perkin transactions II, 1991, # 12, p. 2067 - 2080
  作者：Campbell, John J.、Glover, Stephen A.、Hammond, Gerard P.、Rowbottom, Colleen A.

  DOI：——

  日期：——
• 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.