N-[3-Benzyloxy-4-oxo-cyclohexa-2,5-dien-(E)-ylidene]-benzenesulfonamide | 168648-80-4

• 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-[3-Benzyloxy-4-oxo-cyclohexa-2,5-dien-(E)-ylidene]-benzenesulfonamide
• 英文别名: N-(4-oxo-3-phenylmethoxycyclohexa-2,5-dien-1-ylidene)benzenesulfonamide
• CAS: 168648-80-4
• 化学式: C₁₉H₁₅NO₄S
• 分子量: 353.398
• InChiKey: OOPYBYSFLZUMBK-UHFFFAOYSA-N

物化性质

• 沸点：
  560.3±60.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  81.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-tosyl-7-methoxy-1,2-dihydroquinoline 、 N-[3-Benzyloxy-4-oxo-cyclohexa-2,5-dien-(E)-ylidene]-benzenesulfonamide 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以53%的产率得到N-<(6aS*,11aS*)-10-(benzyloxy)-3-methoxy-5-(4-toluenesulfonyl)-6,6a,11,11a-tetrahydrobenzofuro<3,2-c><1>quinoline-8-yl>benzenesulfonamide
  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
• 作为产物：
  描述：

  2-(苄氧基)-1-甲氧基-4-硝基苯 在 ammonium cerium(IV) nitrate 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 反应 31.25h， 生成 N-[3-Benzyloxy-4-oxo-cyclohexa-2,5-dien-(E)-ylidene]-benzenesulfonamide
  参考文献：
  名称：

  Lewis Acid-Controlled Regioselectivity in Reactions of Styrenyl Systems with Benzoquinone Monoimides:  New Regioselective Syntheses of Substituted 2-Aryl-2,3-dihydrobenzofurans, 2-Aryl-2,3-dihydroindoles, and 2-Arylindoles

  摘要：

  Reactions of 4-(N-phenylsulfonyl)-2-alkoxy-1,4-benzoquinone monoimines 2-4 with electron-rich propenylbenzenes promoted by BF3 yield 7-alkoxy-2-aryl-3-methyl-5-[(N-phenylsulfonyl)amino]2,3-dihydrobenzofurans 5-7 nearly exclusively, whereas promotion of the reactions by Ti4+ gives mixtures of the dihydrobenzofurans and their N-(phenylsulfonyl)-6-alkoxy-2-aryl-5-hydroxy-3-methyl-2,3-dihydroindole isomers 8-10, depending upon substituents present on the propenylbenzene. However, reactions promoted with excess Ti4+, as mixtures of TiCl4:Ti(OiPr)(4), give the dihydroindoles as nearly the exclusive products. Evidence for a mechanism involving initial 5 + 2 cycloaddition of the Lewis acid-bound quinone monoimide with the propenylbenzene is found in reactions of styrenes 1f/g with monoimide 3 in which 7-aryl-3-hydroxy-6-methylbicyclo[3.2.1]oct-3-ene-2,8-diones 33 (5 + 2 adducts) are isolated. These reactions have been applied to stereoselective syntheses of pterocarpans bearing N-phenylsulfonyl groups, azapterocarpans and diazapterocarpans. In addition, DDQ oxidation of derivatives of several of the 2-aryl-2,3-dihydroindoles afford the corresponding 2-arylindoles in good yield. Finally, the experimental details of a general synthetic approach to 7-alkoxy-benzofuranoid neolignans, including (+/-)-licarin B and eupomatenoids-1 and -12 are reported.

  DOI：

  10.1021/jo9617068

文献信息

• 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。
• Switchable regioselectivity in lewis acid-promoted reactions of 1,4-benzoquinone monoimides with styrenyl systems: Selective syntheses of either 2-aryl-2,3-dihydrobenzofurans or 2-aryl-2,3-dihydroindoles
  作者：Thomas A. Engler、Wenying Chai、Kenneth O. Lynch

  DOI：10.1016/0040-4039(95)01449-r

  日期：1995.9

  Reactions of 4-(N-phenylsulfonyl)-2-alkoxy-1,4-benzoquinone monoimines with electron-rich propenylbenzenes promoted by BF3 yield 7-alkoxy-2-aryl-3-methyl-5-(N-phenylsulfonyl)amino-2,3-dihydrobenzofurans nearly exclusively; whereas, promotion of the reactions by >2 equiv of Ti(IV) gives mainly N-phenylsulfonyl-6alkoxy-2-aryl-5-hydroxy-3-methyl-2,3-dihydoinidoles.