N-(3-methoxy-4-oxo-2,5-cyclohexadien-1-ylidene)benzenesulfonamide | 168648-79-1

• 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-methoxy-4-oxo-2,5-cyclohexadien-1-ylidene)benzenesulfonamide
• 英文别名: N-(3-methoxy-4-oxocyclohexa-2,5-dien-1-ylidene)benzenesulfonamide
• CAS: 168648-79-1
• 化学式: C₁₃H₁₁NO₄S
• 分子量: 277.301
• InChiKey: NMPUNGDNTXBODD-UHFFFAOYSA-N

物化性质

• 沸点：
  458.5±55.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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-(3-methoxy-4-oxo-2,5-cyclohexadien-1-ylidene)benzenesulfonamide 在 三甲基氯硅烷 、 tris(dibenzylideneacetone)dipalladium (0) 、 三(2-呋喃基)膦 、 蒽 、 三氟化硼乙醚 、 potassium tert-butylate 、 sodium 、 potassium carbonate 、 溶剂黄146 、 三氟乙酸 、 sodium iodide 、 lithium chloride 、 sodium nitrite 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 2.0h， 生成 (+)-利卡灵
  参考文献：
  名称：

  Synthesis of (±)-licarin B and eupomatenoids-1 and -12: A general approach to 2-aryl-7-alkoxy-benzofuranoid neolignans

  摘要：

  New syntheses of the title compounds are described using Lewis acid-promoted reactions of styrenes with N-phenylsulfonyl-1,4-benzoquinone monoimines to regioselectively form the 2-arylbenzofuranoid ring system followed by conversion of the aromatic N-phenylsulfonyl moiety into a propenyl substituent. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)01619-x
• 作为产物：
  描述：

  N-(3,4-二甲氧基苯基)苯磺酰胺 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 以64%的产率得到N-(3-methoxy-4-oxo-2,5-cyclohexadien-1-ylidene)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

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。
• The three component reaction involving isocyanides, dimethyl acetylenedicarboxylate and quinoneimides: a facile synthesis of spirofused γ-iminolactams
  作者：Vijay Nair、R. Dhanya、S. Viji

  DOI：10.1016/j.tet.2005.04.008

  日期：2005.6

  The three component reaction of the zwitterion generated from dimethyl acetylenedicarboxylate and isocyanides with various quinoneimides is described. The reaction afforded the corresponding γ-spiroiminolactams in good yields.

  描述了由乙炔二羧酸二甲酯和异氰酸酯产生的两性离子与各种醌酰亚胺的三组分反应。该反应以良好的产率提供了相应的γ-螺氨基内酰胺。
• 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.
• 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
  作者：Thomas A. Engler、Wenying Chai、Kenneth O. LaTessa

  DOI：10.1021/jo9617068

  日期：1996.1.1

  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.