N-[(4-chlorophenyl)sulfonyl]-2-phenylacetamide | 1788-12-1

• 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-[(4-chlorophenyl)sulfonyl]-2-phenylacetamide
• 英文别名: N-Phenylacetyl-4-chlor-benzolsulfonamid
• CAS: 1788-12-1
• 化学式: C₁₄H₁₂ClNO₃S
• 分子量: 309.773
• InChiKey: JDXYHOWUPVYHTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  63.24
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-氯苯磺酰胺 、 苯乙酸乙酯 在 四氯化钛 作用下， 以 甲苯 为溶剂， 反应 24.17h， 以22%的产率得到N-[(4-chlorophenyl)sulfonyl]-2-phenylacetamide
  参考文献：
  名称：

  Titanium-Promoted Acylation of Sulfonamides toN-Acylsulfonamide PPARαAntagonists

  摘要：

  The direct acylation of sulfonamides by esters represents an attractive strategy in organic chemistry, being an interesting alternative to classical approaches to N-acylsulfonamides. Here is described a simple and effective method to obtain N-acylsulfonamides of pharmaceutical interest, in a reaction promoted by titanium(IV) chloride. This strategy was successfully applied to the synthesis of a peroxisome proliferator-activated receptor antagonist with a benzenesulfonimide moiety, ensuring an excellent yield of product. The reaction was further studied to explore the behavior of different -bromoesters and esters and the effects of para-substitution in the benzenesulfonamide moiety.

  DOI：

  10.1080/00397911.2015.1092552