N-[4-(benzenesulfonylimino)-2-methoxycyclohexa-2,5-dien-1-ylidene]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-[4-(benzenesulfonylimino)-2-methoxycyclohexa-2,5-dien-1-ylidene]benzamide
• 化学式: C₂₀H₁₆N₂O₄S
• 分子量: 380.424
• InChiKey: VBRZZGCUZXXUTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  93.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[4-(benzenesulfonylimino)-2-methoxycyclohexa-2,5-dien-1-ylidene]benzamide 在 三氟化硼乙醚 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 1.5h， 生成 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

文献信息

• Cycloaddition reactions of 1,4-benzoquinone mono- and bisimides with styrenyl systems: New syntheses of nitrogen substituted azapterocarpans, pterocarpans, 2-aryl-2,3-dihydroindoles and -dihydrobenzofurans
  作者：Thomas A. Engler、Kenneth O. Lynch、Wenying Chai、Steven P. Meduna

  DOI：10.1016/0040-4039(95)00375-m

  日期：1995.4

  Lewis acid-promoted reactions of 1,4-benzoquinones and 1,4-benzoquinone bis- and monoimides with various 2H-chromenes, N-tosyl-1,2-dihydroquinolines and styrenes regio- and stereoselectively produce the title compounds in good yields.

  1，4-苯醌，1，4-苯醌双和单酰亚胺与各种2 H-色烯，N-甲苯磺酰基-1,2-二氢喹啉和苯乙烯的路易斯酸促进反应，区域和立体选择性地产生标题化合物，收率高。
• Lewis Acid-Directed Reactions of Benzoquinone Mono-/Bis-imines: Application to Syntheses of Substituted β- and γ-Tetrahydrocarbolines
  作者：Thomas A Engler、Jutta Wanner

  DOI：10.1016/s0040-4039(97)01391-9

  日期：1997.9

  Ti(IV)-promoted reactions of N-phenylsulfonyl-3- and 4-piperidone enol ethers with 2-alkoxy-4-(N-phenylsulfonyl)imino-1,4-benzoquinone afford 8-alkoxy-7-hydroxy-tetrahydrocarbolines. However, reactions promoted by BF3 produce substituted benzofurans. Ti(IV)- or BF3-promoted reactions of 2-alkoxy-1-(N-benzoyl)-4-(N-phenylsulfonyl)-1,4-benzoquinone bisimines also afford substituted tetrahydrocarboline

  N-苯基磺酰基-3-和4-哌啶酮烯醇醚与2-烷氧基-4-（N-苯基磺酰基）亚氨基-1,4-苯醌的Ti（IV）促进反应生成8-烷氧基-7-羟基-四氢咔啉。然而，由BF 3促进的反应产生取代的苯并呋喃。Ti（IV）-或BF 3促进的2-烷氧基-1-（N-苯甲酰基）-4-（N-苯磺酰基）-1,4-苯醌双亚胺的反应也提供了取代的四烃基衍生物。©1997爱思唯尔科学有限公司。