N-((2R*,3R*)-1-benzenesulfonyl-2-[1,3]benzodioxolyl-6-methoxy-3-methyl-2,3-dihydro-1H-indol-5-yl)benzamide

• 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-((2R*,3R*)-1-benzenesulfonyl-2-[1,3]benzodioxolyl-6-methoxy-3-methyl-2,3-dihydro-1H-indol-5-yl)benzamide
• 英文别名: N-[(2S,3S)-1-(benzenesulfonyl)-2-(1,3-benzodioxol-5-yl)-6-methoxy-3-methyl-2,3-dihydroindol-5-yl]benzamide
• 化学式: C₃₀H₂₆N₂O₆S
• 分子量: 542.612
• InChiKey: SHIUQQZEBHIXNO-SLQAJWMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-((2R*,3R*)-1-benzenesulfonyl-2-[1,3]benzodioxolyl-6-methoxy-3-methyl-2,3-dihydro-1H-indol-5-yl)benzamide 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 1.5h， 以90%的产率得到N-(1-benzenesulfonyl-2-[1,3]benzodioxolyl-6-methoxy-3-methyl-1H-indol-5-yl)benzamide
  参考文献：
  名称：

  Lewis Acid-Promoted Reactions of Styrenyl Systems with Benzoquinone Bisimines:  New Regioselective Syntheses of Substituted 2-Aryl-2,3-dihydroindoles and 2-Arylindoles

  摘要：

  BF3-promoted reactions of 2-alkoxy-1-(N-benzoyl)-4-(N-benzenesulfonyl)-1,4-benzoquinone bisimines (2/3) with beta-methylstyrenes yield trans-5-(N-benzoylamino)-6-alkoxy-2-aryl-3-methyl-2,3-dihydroindoles (4/5) or 3-(N-benzoylamino)-6-aryl-7-methyl-4,8-dioxobicyclo[3.2.1]oct-2-enes (6) regio- and stereoselectively. The former are produced in reactions with styrenes bearing alkoxy substituents, whereas with neutral or electron deficient styrenes, the latter are found. As applications of this new methodology to the synthesis of biologically interesting molecules, reactions of 2H-chromenes and 7-methoxy-N-toluenesulfonyl-1,2-dihydroquinoline with the bisimines have been developed as routes to substituted aza- and diazapterocarpans. Syntheses of 2-arylindoles via oxidation of the dihydroindoles 4 are also reported.

  DOI：

  10.1021/jo9613592
• 作为产物：
  描述：

  N-[4-(benzenesulfonylimino)-2-methoxycyclohexa-2,5-dien-1-ylidene]benzamide 、 异黄樟素 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到N-((2R*,3R*)-1-benzenesulfonyl-2-[1,3]benzodioxolyl-6-methoxy-3-methyl-2,3-dihydro-1H-indol-5-yl)benzamide
  参考文献：
  名称：

  Lewis Acid-Promoted Reactions of Styrenyl Systems with Benzoquinone Bisimines:  New Regioselective Syntheses of Substituted 2-Aryl-2,3-dihydroindoles and 2-Arylindoles

  摘要：

  BF3-promoted reactions of 2-alkoxy-1-(N-benzoyl)-4-(N-benzenesulfonyl)-1,4-benzoquinone bisimines (2/3) with beta-methylstyrenes yield trans-5-(N-benzoylamino)-6-alkoxy-2-aryl-3-methyl-2,3-dihydroindoles (4/5) or 3-(N-benzoylamino)-6-aryl-7-methyl-4,8-dioxobicyclo[3.2.1]oct-2-enes (6) regio- and stereoselectively. The former are produced in reactions with styrenes bearing alkoxy substituents, whereas with neutral or electron deficient styrenes, the latter are found. As applications of this new methodology to the synthesis of biologically interesting molecules, reactions of 2H-chromenes and 7-methoxy-N-toluenesulfonyl-1,2-dihydroquinoline with the bisimines have been developed as routes to substituted aza- and diazapterocarpans. Syntheses of 2-arylindoles via oxidation of the dihydroindoles 4 are also reported.

  DOI：

  10.1021/jo9613592

文献信息

• Lewis Acid-Promoted Reactions of Styrenyl Systems with Benzoquinone Bisimines:  New Regioselective Syntheses of Substituted 2-Aryl-2,3-dihydroindoles and 2-Arylindoles
  作者：Thomas A. Engler、Steven P. Meduna、Kenneth O. LaTessa、Wenying Chai

  DOI：10.1021/jo9613592

  日期：1996.1.1

  BF3-promoted reactions of 2-alkoxy-1-(N-benzoyl)-4-(N-benzenesulfonyl)-1,4-benzoquinone bisimines (2/3) with beta-methylstyrenes yield trans-5-(N-benzoylamino)-6-alkoxy-2-aryl-3-methyl-2,3-dihydroindoles (4/5) or 3-(N-benzoylamino)-6-aryl-7-methyl-4,8-dioxobicyclo[3.2.1]oct-2-enes (6) regio- and stereoselectively. The former are produced in reactions with styrenes bearing alkoxy substituents, whereas with neutral or electron deficient styrenes, the latter are found. As applications of this new methodology to the synthesis of biologically interesting molecules, reactions of 2H-chromenes and 7-methoxy-N-toluenesulfonyl-1,2-dihydroquinoline with the bisimines have been developed as routes to substituted aza- and diazapterocarpans. Syntheses of 2-arylindoles via oxidation of the dihydroindoles 4 are also reported.