2-formyl-N-(2-phenylpropan-2-yl)benzenesulfonamide | 936841-21-3

• 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: 2-formyl-N-(2-phenylpropan-2-yl)benzenesulfonamide
• CAS: 936841-21-3
• 化学式: C₁₆H₁₇NO₃S
• 分子量: 303.382
• InChiKey: HBJWXYYAIHABCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-formyl-N-(2-phenylpropan-2-yl)benzenesulfonamide 在 四甲基乙二胺 、 仲丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 24.0h， 生成 7-iodo-2-(2-phenylpropan-2-yl)-3-(trimethylsilyloxy)-2,3-dihydrobenzo[d]isothiazole 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 sodium azide 、 四甲基乙二胺 、 氢气 、 仲丁基锂 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 氯仿 、 环己烷 为溶剂， 反应 26.0h， 生成 2-formyl-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