N-(3-isobutoxy-4-methoxyphenyl)benzenesulfonamide | 185145-97-5

• 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-isobutoxy-4-methoxyphenyl)benzenesulfonamide
• 英文别名: N-[4-methoxy-3-(2-methylpropoxy)phenyl]benzenesulfonamide
• CAS: 185145-97-5
• 化学式: C₁₇H₂₁NO₄S
• 分子量: 335.424
• InChiKey: GZAIQNJIRDBFDI-UHFFFAOYSA-N

物化性质

• 沸点：
  462.6±55.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  73
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3-isobutoxy-4-methoxyphenyl)benzenesulfonamide 在 titanium(IV) isopropylate 、 ammonium cerium(IV) nitrate 、 四氯化钛 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.5h， 生成 (2R*,3R*)-1-(benzenesulfonyl)-2,3-dihydro-5-hydroxy-6-isobutoxy-3-methyl-2-<3,4-(methylenedioxy)phenyl>indole
  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
• 作为产物：
  描述：

  2-甲氧基-5-硝基苯酚 在 四丁基碘化铵 、 potassium carbonate 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 乙酸乙酯 、 丙酮 为溶剂， 反应 86.0h， 生成 N-(3-isobutoxy-4-methoxyphenyl)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