4-methoxy-2-phenyl-N-(2-phenylpropan-2-yl)benzenesulfonamide | 936841-49-5

• 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: 4-methoxy-2-phenyl-N-(2-phenylpropan-2-yl)benzenesulfonamide
• CAS: 936841-49-5
• 化学式: C₂₂H₂₃NO₃S
• 分子量: 381.496
• InChiKey: GBBSWWJOHWYJKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxy-2-phenyl-N-(2-phenylpropan-2-yl)benzenesulfonamide 在 正丁基锂 、 四甲基乙二胺 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 13.17h， 生成 5-methoxy-7-phenylbenzo[d]isothiazol-3(2H)-one 1,1-dioxide
  参考文献：
  名称：

  Directed Ortho Metalation−Cross Coupling Strategies. N-Cumyl Arylsulfonamides. Facile Deprotection and Expedient Route to 7- and 4,7-Substituted Saccharins

  摘要：

  By using the powerful N-cumylsulfonamide directed metalation group (DMG), a series of 2-substituted derivatives were prepared according to the directed ortho metalation (DoM) tactic (Table 1). Mild conditions for N-decumylation and other simple transformations of the products have been achieved (Scheme 2). The 3-silyloxy sultam 12 undergoes further DoM to give formyl, thiomethyl, iodo, and amide derivatives 13a-g of potential value for saccharin synthesis (Table 2). An effective route to target 7-aryl saccharins via Suzuki cross coupling (Table 3) followed by further metalation-carbamoylation and cyclization (Table 5) is described. 4,7-Disubstituted saccharins have been obtained by similar sequences (Scheme 3). Mild TFA-mediated N-decumylation furnishes substituted primary arylsulfonamides (Table 4).

  DOI：

  10.1021/jo062385v
• 作为产物：
  描述：

  2-苯基-2-丙醇 在 Lindlar's catalyst 、 四(三苯基膦)钯 正丁基锂 、 sodium azide 、 四甲基乙二胺 、 氢气 、 sodium carbonate 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 49.0h， 生成 4-methoxy-2-phenyl-N-(2-phenylpropan-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Directed Ortho Metalation−Cross Coupling Strategies. N-Cumyl Arylsulfonamides. Facile Deprotection and Expedient Route to 7- and 4,7-Substituted Saccharins

  摘要：

  By using the powerful N-cumylsulfonamide directed metalation group (DMG), a series of 2-substituted derivatives were prepared according to the directed ortho metalation (DoM) tactic (Table 1). Mild conditions for N-decumylation and other simple transformations of the products have been achieved (Scheme 2). The 3-silyloxy sultam 12 undergoes further DoM to give formyl, thiomethyl, iodo, and amide derivatives 13a-g of potential value for saccharin synthesis (Table 2). An effective route to target 7-aryl saccharins via Suzuki cross coupling (Table 3) followed by further metalation-carbamoylation and cyclization (Table 5) is described. 4,7-Disubstituted saccharins have been obtained by similar sequences (Scheme 3). Mild TFA-mediated N-decumylation furnishes substituted primary arylsulfonamides (Table 4).

  DOI：

  10.1021/jo062385v