N-<(6aS*,11aS*)-6,6a,11,11a-tetrahydro-3,9-dimethoxy-11-(benzenesulfonyl)<1>benzopyrano<4,3-b>indol-8-yl>benzamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: N-<(6aS*,11aS*)-6,6a,11,11a-tetrahydro-3,9-dimethoxy-11-(benzenesulfonyl)<1>benzopyrano<4,3-b>indol-8-yl>benzamide
• 英文别名: N-[(6aR,11aS)-11-(benzenesulfonyl)-3,9-dimethoxy-6a,11a-dihydro-6H-chromeno[4,3-b]indol-8-yl]benzamide
• 化学式: C₃₀H₂₆N₂O₆S
• 分子量: 542.612
• InChiKey: DQFILWGRJGCWTG-FUFSCUOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 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

• 作为产物：
  描述：

  3-chromene 、 N-[4-(benzenesulfonylimino)-2-methoxycyclohexa-2,5-dien-1-ylidene]benzamide 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以63%的产率得到N-<(6aS*,11aS*)-6,6a,11,11a-tetrahydro-3,9-dimethoxy-11-(benzenesulfonyl)<1>benzopyrano<4,3-b>indol-8-yl>benzamide
  参考文献：
  名称：

  1,4-苯醌单-和双酰亚胺与苯乙烯基体系的环加成反应：氮取代的氮杂ero果，蝶果，2-芳基-2,3-二氢吲哚和-二氢苯并呋喃的新合成

  摘要：

  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。

  DOI：

  10.1016/0040-4039(95)00375-m

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.
• 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。