methyl 3-((N-(2-bromobenzyl)-2-methylphenyl)sulfonamido)thiophene-2-carboxylate | 1374831-19-2

• 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: methyl 3-((N-(2-bromobenzyl)-2-methylphenyl)sulfonamido)thiophene-2-carboxylate
• CAS: 1374831-19-2
• 化学式: C₂₀H₁₈BrNO₄S₂
• 分子量: 480.403
• InChiKey: RTOCCTKMRFZNGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.0
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 3-((N-(2-bromobenzyl)-2-methylphenyl)sulfonamido)thiophene-2-carboxylate 在 palladium diacetate 、 potassium carbonate 、 caesium carbonate 、 三甲基丙酮酸 、 tricyclohexylphosphine tetrafluoroborate 、 sodium hydroxide 、 palladium dichloride 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 2,4-滴二甲胺盐 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.13h， 生成 1-(3-methoxyphenyl)-4-(o-tolylsulfonyl)-4,5-dihydrothieno[3,4-c]isoquinoline
  参考文献：
  名称：

  A One-Pot Double C–H Activation Palladium Catalyzed Route to a Unique Class of Highly Functionalized Thienoisoquinolines

  摘要：

  The synthesis of a unique class of highly functionalized 3,4-thienoisoquinolines via an efficient palladium-catalyzed one-pot, regioselective double C H activation is presented. This class of biologically relevant compounds has been prepared in five steps from commercially available starting materials with overall yields ranging from 27 to 62%. A masked carboxylic acid was used to direct C H activation to the typically less reactive C4 position. Additionally, the carboxylic acid provides a synthetically useful handle for further functionalization.

  DOI：

  10.1021/ol3009655
• 作为产物：
  描述：

  3-氨基-2-噻吩甲酸甲酯 在 吡啶 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 methyl 3-((N-(2-bromobenzyl)-2-methylphenyl)sulfonamido)thiophene-2-carboxylate
  参考文献：
  名称：

  A One-Pot Double C–H Activation Palladium Catalyzed Route to a Unique Class of Highly Functionalized Thienoisoquinolines

  摘要：

  The synthesis of a unique class of highly functionalized 3,4-thienoisoquinolines via an efficient palladium-catalyzed one-pot, regioselective double C H activation is presented. This class of biologically relevant compounds has been prepared in five steps from commercially available starting materials with overall yields ranging from 27 to 62%. A masked carboxylic acid was used to direct C H activation to the typically less reactive C4 position. Additionally, the carboxylic acid provides a synthetically useful handle for further functionalization.

  DOI：

  10.1021/ol3009655