N-(4-苯甲酰基苯基)苯磺酰胺 | 124400-29-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(4-苯甲酰基苯基)苯磺酰胺
• 英文名称: 4-<(Benzenesulfonyl)amino>benzophenone
• 英文别名: p-[(benzenesulfonyl)amino]benzophenone；N-4-benzoylphenyl benzenesulfonamide；benzenesulfonic acid-(4-benzoyl-anilide)；Benzolsulfonsaeure-(4-benzoyl-anilid)；4-Benzolsulfamino-benzophenon；Benzenesulfonamide, N-(4-benzoylphenyl)-；N-(4-benzoylphenyl)benzenesulfonamide
• CAS: 124400-29-9
• 化学式: C₁₉H₁₅NO₃S
• 分子量: 337.399
• InChiKey: UVAGQTHTLGCCNG-UHFFFAOYSA-N

物化性质

• 沸点：
  520.4±52.0 °C(Predicted)
• 密度：
  1.314±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-苯甲酰基苯基)苯磺酰胺 在 potassium hypochlorite 、 乙醇 、 potassium dicarbonate 作用下， 生成 benzenesulfonic acid-(4-benzoyl-N-chloro-anilide)
  参考文献：
  名称：

  Chattaway, Journal of the Chemical Society, 1904, vol. 85, p. 394

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氨基二苯甲酮 、 苯磺酰氯 在 吡啶 作用下， 反应 12.0h， 以68%的产率得到N-(4-苯甲酰基苯基)苯磺酰胺
  参考文献：
  名称：

  N-芳基苯磺酰胺抑制剂在人肝细胞衍生的Huh-7癌细胞中[ 3 H]-胸苷掺入和β-catenin信号传导的抑制作用

  摘要：

  作为确定抑制Wnt /β-catenin信号通路的药物的程序的一部分，研究了2,5-二氯-N-（2-甲基-4-硝基苯基）苯磺酰胺（FH535）中的结构活性关系（SAR）。在肝细胞癌（HCC）中经常被上调。据报道，FH535是Wnt信号通路中β-catenin和过氧化物酶体增殖物激活受体（PPAR）的抑制剂。β-catenin/ T细胞因子（TCF）/淋巴增强因子（LEF）依赖性测定（即基于荧光素酶的TOPFlash测定）以及[ 3用1 H-胸苷掺入法研究FH535的SAR修饰。尽管用2,6-二卤代模式代替FH535中的2,5-二氯苯基磺酰基取代基通常会产生比FH535更多的生物活性类似物，但其他SAR修饰仅导致在这两种测定中具有可比或略微提高活性的FH535类似物。活动中没有清晰的SAR模式表明N-芳基苯磺酰胺有多种靶效应子。

  DOI：

  10.1016/j.bmcl.2015.07.040

文献信息

• Synthesis and Antimicrobial Activity of Some New Cyanopyridines, Isoxazoles, Pyrazoles, and Pyrimidines Bearing Sulfonamide Moiety
  作者：Osama S. Moustafa、Ragaa A. Ahmad

  DOI：10.1080/10426500307933

  日期：2003.3.1

  yield the corresponding chalcones 4a-f . On condensation of latter chalcones with malononitrile afford cyanopyridines 5a-f , the reaction of chalcones 4a-f with hyroxylamine hydrochloride furnished isoxazoles 6a-f , while condensation of chalcones with hyrazine hydrate afforded pyrazoline derivatives 7 , 8 . Urea or thiourea was reacted with chalcone 4b to yield pyrimidine derivatives 9 , 10 . The reaction

  对氨基苯乙酮 1 与对取代苯磺酰氯 2a、b 在吡啶中反应得到对乙酰基衍生物 3a、b，然后与芳醛缩合得到相应的查耳酮 4a-f。后面的查耳酮与丙二腈缩合得到氰基吡啶 5a-f，查耳酮 4a-f 与盐酸羟胺反应得到异恶唑 6a-f，而查耳酮与水合肼缩合得到吡唑啉衍生物 7、8。尿素或硫脲与查耳酮 4b 反应生成嘧啶衍生物 9、10。磺酰氯 2a、b 与对氨基二苯甲酮反应生成对 [(苯磺酰基)酰氨基]二苯甲酮 11a、b，然后与水合肼缩合得到相应的腙衍生物 12a、b。
• Stereoselectivity in the Wittig Reaction of Aromatic Ketones: Origin of Preference for the Olefin Geometry
  作者：Kumiko Takeuchi、Jonathan W. Paschal、Richard J. Loncharich

  DOI：10.1021/jo00106a029

  日期：1995.1

  Investigation of the stereoselectivity observed in the Wittig reaction of aromatic ketones with ''nonstabilized'' phosphonium ylides revealed that the nature of the substituent on the phenyl ring of phenyl S-pyridyl ketone determined the stereoselectivity. Generally the Wittig reaction of such ketones with carboxy phosphonium ylides proceeded preferentially to yield (Z)-olefin, albeit with modest selectivity. However, the reaction with aryl sulfonamido-substituted aromatic ketones resulted in high (E)-stereoselectivity. In order to understand the origin of this high (E)-selectivity, a semiempirical conformational analysis of the four uncharged diastereomeric oxaphosphetane intermediates was performed with a cumulatively modified sampling procedure to generate initial conformations, followed by full energy optimization. Computational studies of the unsubstituted and 4-nitrophenyl-substituted oxaphosphetane intermediates were consistent with the low (Z)stereoselectivity observed. The results in the calculations of the aryl sulfonamido-substituted intermediate likewise were consistent with the high (E)-stereoselectivity observed. Calculations of the potassium-coordinated acid anion of the latter species were also performed. All calculations supported interaction of the sulfonamido and carboxylate groups by either hydrogen bonding or salt bridge formation which appears to effect the final stereochemical outcome. Furthermore, we investigated the stereoselectivity of Wittig reactions in which the sulfonamido NH or the carboxylate were removed. In both cases, the (Z)-olefin was formed preferentially, thereby supporting the existence of intramolecular hydrogen bonding or salt bridge formation.