N-(2-phenylpropan-2-yl)-2-trimethylsilylbenzenesulfonamide | 249764-95-2

• 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-(2-phenylpropan-2-yl)-2-trimethylsilylbenzenesulfonamide
• CAS: 249764-95-2
• 化学式: C₁₈H₂₅NO₂SSi
• 分子量: 347.553
• InChiKey: GWLWQWQJVSBCTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-phenylpropan-2-yl)-2-trimethylsilylbenzenesulfonamide 在 三氟乙酸 作用下， 反应 0.17h， 以85%的产率得到2-trimethylsilylbenzenesulfonamide
  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 N-(2-phenylpropan-2-yl)-2-trimethylsilylbenzenesulfonamide
  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

文献信息

• <i>N</i>-Cumyl Benzamide, Sulfonamide, and Aryl <i>O</i>-Carbamate Directed Metalation Groups. Mild Hydrolytic Lability for Facile Manipulation of Directed Ortho Metalation Derived Aromatics
  作者：Costa Metallinos、Sven Nerdinger、Victor Snieckus

  DOI：10.1021/ol990846b

  日期：1999.10.1

  [GRAPHICS]N-Cumyl benzamide (2), sulfonamide (8), and O-carbamate (11) compounds undergo directed ortho metalation under standard conditions to give, after quench with a variety of electrophiles, the substituted products 3, 9, and 12, respectively. Regiospecific and convenient approaches to phthalimides (7), 1,2-benzisothiazole 1,1-dioxides (10b), and ortho-substituted phenols (13a) and salicylamides (13b) are thereby established. The mild deprotection protocol for these new cumyl directed metalation groups (DMGs) suggests that they will supersede previous corresponding groups for synthetic anionic aromatic chemistry.
• Directed <i>Ortho</i> Metalation−Cross Coupling Strategies. <i>N</i>-Cumyl Arylsulfonamides. Facile Deprotection and Expedient Route to 7- and 4,7-Substituted Saccharins
  作者：Jérôme Blanchet、Todd Macklin、Patrick Ang、Costa Metallinos、Victor Snieckus

  DOI：10.1021/jo062385v

  日期：2007.4.1

  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).