N-<(2R*,3R*)-2,3-dihydro-7-methoxy-3-methyl-2-<(3,4-methylenedioxy)phenyl>benzofuran-5-yl>benzenesulfonamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: N-<(2R*,3R*)-2,3-dihydro-7-methoxy-3-methyl-2-<(3,4-methylenedioxy)phenyl>benzofuran-5-yl>benzenesulfonamide
• 英文别名: N-[(2S,3S)-2-(1,3-benzodioxol-5-yl)-7-methoxy-3-methyl-2,3-dihydro-1-benzofuran-5-yl]benzenesulfonamide
• 化学式: C₂₃H₂₁NO₆S
• 分子量: 439.489
• InChiKey: SOMIBSBSJNQTFC-FPTDNZKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  91.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-(3,4-二甲氧基苯基)苯磺酰胺 在 ammonium cerium(IV) nitrate 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.17h， 生成 N-<(2R*,3R*)-2,3-dihydro-7-methoxy-3-methyl-2-<(3,4-methylenedioxy)phenyl>benzofuran-5-yl>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

• 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.