benzoic acid-(4-sec-butyl-anilide) | 107276-61-9

• 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: benzoic acid-(4-sec-butyl-anilide)
• 英文别名: Benzoesaeure-(4-sec-butyl-anilid)；2-<4-Benzamino-phenyl>-butan；N-(4-butan-2-ylphenyl)benzamide
• CAS: 107276-61-9
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: MLHHTJZEKDWYRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  benzoic acid-(4-sec-butyl-anilide) 在 水 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 以45%的产率得到N-Benzoyl-4-hydroxy-3-sec-butylaniline
  参考文献：
  名称：

  Preparation of quinol N-acyl- and quinol ether imines via anodic oxidation of para-substituted anilide derivatives

  摘要：

  Anodic oxidation of N-benzoyl-4-methylaniline in 5 % aqueous methanol in the presence of sodium bicarbonate affords two major products: 4-methoxy-4-methylbenzoquinol N-benzoylimine, 8a, and a dimer, 4-[N-benzoyl-N-(4-methylphenyl)amino]-4-methylbenzoquinol N-benzoylimine, 9. The ratio of these two products was temperature dependent, and conditions were developed for preparing 8a and 9 in good yield. Using the conditions developed for 8a, the anodic methoxylation of N-benzoyl and acetyl derivatives of 4-ethyl- and 4-sec-butyl-4-phenylaniline and 2-aminofluorene derivatives was performed. The yields of the N-benzoyl derivatives of the 4-methoxy-4-substituted-benzoquinol imines were 46-80%, while the N-acetyl derivatives gave lower yields. When the anodic oxidation was performed using 30% water/acetonitrile or 10 % water/tetrahydrofuran, the 4-alkylbenzoquinol N-benzoylimine derivatives were obtained. The yields of these anodic hydroxylation reactions were lower than those of the corresponding methoxylations for all systems studied. In addition, the 4-alkylbenzoquinol N-benzoylimine derivatives were much more labile. Two methods were developed for conversion of the 4-methoxy-4-substituted-benzoquinol N-acylimines to the 4-methoxy-4-substituted-benzoquinol N-alkylimines. Finally, the especially labile 4-hydroxy-4-phenylbenzoquinol N-acetylimine was prepared for the first time from the readily available N-benzoyl derivative.

  DOI：

  10.1021/jo00073a016
• 作为产物：
  描述：

  4-仲丁基苯胺 、 苯甲酰氯 在 4-乙烯基吡啶 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到benzoic acid-(4-sec-butyl-anilide)
  参考文献：
  名称：

  酰胺高速模拟的协议。新型小分子组织蛋白酶D抑制剂的制备

  摘要：

  已经建立了使用聚合物结合的试剂通过酰基氯，磺酰氯和羧酸与氮亲核试剂偶联来溶液相平行合成新的小分子组织蛋白酶D抑制剂的程序，以促进化学反应和/或有效清除未反应的起始物。材料和反应副产物。苯甲酸银（I）用于促进酰氯与反应性较小的苯胺的偶联。化合物4被鉴定为亚微摩尔组织蛋白酶D抑制剂（IC 50 = 320 nM）。

  DOI：

  10.1016/s0040-4039(99)01972-3

文献信息

• Salesskaja, Zhurnal Obshchei Khimii, 1947, vol. 17, p. 489,494
  作者：Salesskaja

  DOI：——

  日期：——
• COMPOUNDS FOR THE PREVENTION AND TREATMENT OF CARDIOVASCULAR DISEASE
  申请人：RESVERLOGIX CORP.

  公开号：EP2382194A2

  公开（公告）日：2011-11-02
• Preparation of quinol N-acyl- and quinol ether imines via anodic oxidation of para-substituted anilide derivatives
  作者：John S. Swenton、Timothy N. Biggs、William M. Clark

  DOI：10.1021/jo00073a016

  日期：1993.10

  Anodic oxidation of N-benzoyl-4-methylaniline in 5 % aqueous methanol in the presence of sodium bicarbonate affords two major products: 4-methoxy-4-methylbenzoquinol N-benzoylimine, 8a, and a dimer, 4-[N-benzoyl-N-(4-methylphenyl)amino]-4-methylbenzoquinol N-benzoylimine, 9. The ratio of these two products was temperature dependent, and conditions were developed for preparing 8a and 9 in good yield. Using the conditions developed for 8a, the anodic methoxylation of N-benzoyl and acetyl derivatives of 4-ethyl- and 4-sec-butyl-4-phenylaniline and 2-aminofluorene derivatives was performed. The yields of the N-benzoyl derivatives of the 4-methoxy-4-substituted-benzoquinol imines were 46-80%, while the N-acetyl derivatives gave lower yields. When the anodic oxidation was performed using 30% water/acetonitrile or 10 % water/tetrahydrofuran, the 4-alkylbenzoquinol N-benzoylimine derivatives were obtained. The yields of these anodic hydroxylation reactions were lower than those of the corresponding methoxylations for all systems studied. In addition, the 4-alkylbenzoquinol N-benzoylimine derivatives were much more labile. Two methods were developed for conversion of the 4-methoxy-4-substituted-benzoquinol N-acylimines to the 4-methoxy-4-substituted-benzoquinol N-alkylimines. Finally, the especially labile 4-hydroxy-4-phenylbenzoquinol N-acetylimine was prepared for the first time from the readily available N-benzoyl derivative.
• Protocols for amide high-speed analoging. Preparation of novel, small molecule cathepsin D inhibitors
  作者：Jinshan Chen、Brian R. Dixon、Jacques Dumas、David Brittelli

  DOI：10.1016/s0040-4039(99)01972-3

  日期：1999.12

  Procedures for solution phase parallel synthesis of new, small molecule cathepsin D inhibitors by the coupling of acyl chlorides, sulfonyl chlorides and carboxylic acids with nitrogen nucleophiles have been established using polymer-bound reagents to facilitate the chemistry and/or to efficiently scavenge the unreacted starting materials and reaction by-products. Silver(I) benzoate was used to facilitate

  已经建立了使用聚合物结合的试剂通过酰基氯，磺酰氯和羧酸与氮亲核试剂偶联来溶液相平行合成新的小分子组织蛋白酶D抑制剂的程序，以促进化学反应和/或有效清除未反应的起始物。材料和反应副产物。苯甲酸银（I）用于促进酰氯与反应性较小的苯胺的偶联。化合物4被鉴定为亚微摩尔组织蛋白酶D抑制剂（IC 50 = 320 nM）。