tert-butyl 4-(2-methoxy-1-{[methyl(phenyl)amino]sulfonyl}-2-oxoethyl)benzoate | 957070-16-5

• 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: tert-butyl 4-(2-methoxy-1-{[methyl(phenyl)amino]sulfonyl}-2-oxoethyl)benzoate
• 英文别名: Tert-butyl 4-[2-methoxy-1-[methyl(phenyl)sulfamoyl]-2-oxoethyl]benzoate
• CAS: 957070-16-5
• 化学式: C₂₁H₂₅NO₆S
• 分子量: 419.499
• InChiKey: GUXZTDVTSKMUPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  98.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-(2-methoxy-1-{[methyl(phenyl)amino]sulfonyl}-2-oxoethyl)benzoate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 反应 1.5h， 生成 tert-butyl 4-{[(dimethylamino)sulfonyl]methyl}benzoate
  参考文献：
  名称：

  A New Strategy for the Synthesis of Benzylic Sulfonamides:  Palladium-Catalyzed Arylation and Sulfonamide Metathesis

  摘要：

  [GRAPHICS]An efficient two-step strategy has been developed to access diversely functionalized benzylic sulfonamides. Execution of this strategy required the development of two reaction methods: the palladium-catalyzed cross-coupling of aryl halides with CH-acidic methanesulfonamides and a metathesis reaction between the resulting alpha-arylated sulfonamides and diverse amines. The broad scope of the cross-coupling process combined with a versatile sulfonamide metathesis constitutes an efficient strategy for the synthesis of various benzylic sulfonamides.

  DOI：

  10.1021/jo701431j
• 作为产物：
  描述：

  4-溴苯甲酸叔丁酯 、 methyl {[methyl(phenyl)amino]sulfonyl}acetate 在 palladium diacetate sodium t-butanolate 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.5h， 以77%的产率得到tert-butyl 4-(2-methoxy-1-{[methyl(phenyl)amino]sulfonyl}-2-oxoethyl)benzoate
  参考文献：
  名称：

  A New Strategy for the Synthesis of Benzylic Sulfonamides:  Palladium-Catalyzed Arylation and Sulfonamide Metathesis

  摘要：

  [GRAPHICS]An efficient two-step strategy has been developed to access diversely functionalized benzylic sulfonamides. Execution of this strategy required the development of two reaction methods: the palladium-catalyzed cross-coupling of aryl halides with CH-acidic methanesulfonamides and a metathesis reaction between the resulting alpha-arylated sulfonamides and diverse amines. The broad scope of the cross-coupling process combined with a versatile sulfonamide metathesis constitutes an efficient strategy for the synthesis of various benzylic sulfonamides.

  DOI：

  10.1021/jo701431j

文献信息

• A New Strategy for the Synthesis of Benzylic Sulfonamides:  Palladium-Catalyzed Arylation and Sulfonamide Metathesis
  作者：Jonathan B. Grimm、Matthew H. Katcher、David J. Witter、Alan B. Northrup

  DOI：10.1021/jo701431j

  日期：2007.10.1

  [GRAPHICS]An efficient two-step strategy has been developed to access diversely functionalized benzylic sulfonamides. Execution of this strategy required the development of two reaction methods: the palladium-catalyzed cross-coupling of aryl halides with CH-acidic methanesulfonamides and a metathesis reaction between the resulting alpha-arylated sulfonamides and diverse amines. The broad scope of the cross-coupling process combined with a versatile sulfonamide metathesis constitutes an efficient strategy for the synthesis of various benzylic sulfonamides.