4-methyl-N-(1-phenyl-2-(quinolin-2-yl)ethyl)benzenesulfonamide | 1218989-07-1

• 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-methyl-N-(1-phenyl-2-(quinolin-2-yl)ethyl)benzenesulfonamide
• 英文别名: 4-methyl-N-(1-phenyl-2-quinolin-2-ylethyl)benzenesulfonamide
• CAS: 1218989-07-1
• 化学式: C₂₄H₂₂N₂O₂S
• 分子量: 402.517
• InChiKey: CBNQWXUCJGZWSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  573.6±60.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-N-(1-phenyl-2-(quinolin-2-yl)ethyl)benzenesulfonamide 以 甲苯 为溶剂， 以65%的产率得到2-苯乙烯基喹啉
  参考文献：
  名称：

  A Catalyst-Free Benzylic C–H Bond Olefination of Azaarenes for Direct Mannich-like Reactions

  摘要：

  A highly efficient synthesis of trans-alkenylazaarene under catalyst-free conditions was developed via the addition of methylazaarenes to N-sulfonyl aldimines and a subsequent C-N elimination in situ. A one-pot procedure for this addition-elimination was also developed. The reaction could tolerate a broad substrate scope and give the corresponding alkenylazaarenes in high yields.

  DOI：

  10.1021/jo2008934
• 作为产物：
  描述：

  苯甲醛 在 1,10-菲罗啉 、 硅酸四乙酯 、 palladium diacetate 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 4-methyl-N-(1-phenyl-2-(quinolin-2-yl)ethyl)benzenesulfonamide
  参考文献：
  名称：

  A Catalyst-Free Benzylic C–H Bond Olefination of Azaarenes for Direct Mannich-like Reactions

  摘要：

  A highly efficient synthesis of trans-alkenylazaarene under catalyst-free conditions was developed via the addition of methylazaarenes to N-sulfonyl aldimines and a subsequent C-N elimination in situ. A one-pot procedure for this addition-elimination was also developed. The reaction could tolerate a broad substrate scope and give the corresponding alkenylazaarenes in high yields.

  DOI：

  10.1021/jo2008934

文献信息

• Iron-Catalyzed Direct Alkenylation of 2-Substituted Azaarenes with <i>N</i>-Sulfonyl Aldimines via C–H Bond Activation
  作者：Bo Qian、Pan Xie、Yinjun Xie、Hanmin Huang

  DOI：10.1021/ol200684b

  日期：2011.5.20

  A novel iron-catalyzed alkenylation of 2-substituted azaarenes through sp3 C–H bond activation has been developed. A favorable E2-elimination is proposed as a key step to cleavage of C–H and C–N bonds for the construction of a C═C bond in high stereoselectivity. This transformation represents an efficient way to synthesize 2-alkenylated azaarenes from simple starting materials.

  通过sp 3 C–H键活化，已开发出一种新型的铁催化的2-取代的氮杂芳烃的烯基化反应。提出了一种有利的消除E2的方法，作为裂解C–H和C–N键的关键步骤，以高立体选择性构建C═C键。这种转化代表了一种由简单的起始原料合成2-烯基化氮杂芳烃的有效方法。
• Lewis Acid Catalyzed Benzylic C-H Bond Functionalization of Azaarenes; Addition to Imines and Enones
  作者：Shigeki Matsunaga、Motomu Kanai、Hirotomo Komai、Tatsuhiko Yoshino

  DOI：10.1055/s-0031-1291041

  日期：2012.7

  Y(OTf)3, were essential to promote the 1,4-addition of alkyl-substituted azaarenes to enones, and products were obtained in 60–96% yield. Lewis acid catalyzed benzylic C–H bond functionalization of alkyl-substituted azaarenes is described. The addition to N-tosyl imines proceeded under solvent-free conditions using various Lewis acids. Cu(OTf)2 was the best Lewis acid, and 1,2-addition proceeded at

  摘要 描述了路易斯酸催化烷基取代的氮杂芳烃的苄基C–H键官能化。使用各种路易斯酸在无溶剂条件下将N-甲苯磺酰基亚胺加成。Cu（OTf）2是最好的路易斯酸，1,2-加成反应在60–120°C进行，产率为23–92％。另一方面，强路易斯酸性稀土金属三氟甲磺酸酯Sc（OTf）3和Y（OTf）3对于促进烷基取代的氮杂芳烃向烯酮的1,4-加成反应至关重要，得到的产物为60 –96％的产率。 描述了路易斯酸催化烷基取代的氮杂芳烃的苄基C–H键官能化。使用各种路易斯酸在无溶剂条件下将N-甲苯磺酰基亚胺加成。Cu（OTf）2是最好的路易斯酸，1,2-加成反应在60–120°C进行，产率为23–92％。另一方面，强路易斯酸性稀土金属三氟甲磺酸酯Sc（OTf）3和Y（OTf）3对于促进烷基取代的氮杂芳烃向烯酮的1,4-加成反应至关重要，得到的产物为60 –96％的产率。
• Lewis Acid-Catalyzed CH Functionalization for Synthesis of Isoindolinones and Isoindolines
  作者：Bo Qian、Shengmei Guo、Chungu Xia、Hanmin Huang

  DOI：10.1002/adsc.201000556

  日期：2010.12.17

  The Lewis acid-catalyzed CH functionalization of 2-substituted azaarenes with N-sulfonylaldimines has been developed, which provides a rapid and efficient approach for synthesis of heterocycle-containing isoindolinones and isoindolines.

  已经开发了用N-磺酰基醛二胺的路易斯酸催化的2-取代的氮杂芳烃的CH官能化，其为合成含杂环的异吲哚啉酮和异吲哚啉提供了一种快速有效的方法。
• Pd(II)-catalyzed Enantioselective Beta-Methylene C(sp3)–H Bond Activation
  申请人：The Scripps Research Institute

  公开号：US20190315710A1

  公开（公告）日：2019-10-17

  Chiral acetyl-protected aminoethyl quinoline (APAQ), pyridine and imazoline ligands are disclosed that enable Pd (II)-catalyzed enantioselective arylation or heteroarylation of ubiquitous prochiral β-methylene C—H bonds of aliphatic amides offers an alternative disconnection for constructing β-chiral centers. Systematic tuning of the ligand structure reveals that a six-membered instead of a five-membered chelation of these types of ligands with the Pd(II) is important for accelerating the C(sp 3 )-H activation thereby achieving enantioselectivity for quinoline and pyridine ligands.

  披露了手性乙酰保护氨基乙基喹啉（APAQ）、吡啶和咪唑啉配体，这些配体使Pd（II）催化的对丙烷酰胺的普遍的原始手性β-亚甲基C-H键进行对芳基或杂芳基化的不对称选择性取代反应成为可能，为构建β-手性中心提供了另一种断裂途径。通过系统调整配体结构发现，这些类型的配体与Pd（II）的六元环而不是五元环的螯合对于加速C（sp3）-H键的活化至关重要，从而实现喹啉和吡啶配体的对映选择性。
• Pd(II)-catalyzed enantioselective β-methylene C(sp3)—H bond activation
  申请人：The Scripps Research Institute

  公开号：US11186563B2

  公开（公告）日：2021-11-30

  Chiral acetyl-protected aminoethyl quinoline (APAQ), pyridine and imazoline ligands are disclosed that enable Pd (II)-catalyzed enantioselective arylation or heteroarylation of ubiquitous prochiral β-methylene C—H bonds of aliphatic amides offers an alternative disconnection for constructing β-chiral centers. Systematic tuning of the ligand structure reveals that a six-membered instead of a five-membered chelation of these types of ligands with the Pd(II) is important for accelerating the C(sp3)-H activation thereby achieving enantioselectivity for quinoline and pyridine ligands.

  本研究公开了手性乙酰基保护的氨基乙基喹啉 (APAQ)、吡啶和咪唑啉配体，这些配体能够在钯(II)催化下对无处不在的脂肪族酰胺的原手性 β-亚甲基 C-H 键进行对映选择性芳基化或杂芳基化，为构建 β-手性中心提供了另一种断开方式。配体结构的系统调整表明，这些配体与 Pd(II) 的六元螯合而非五元螯合对于加速 C(sp3)-H 活化非常重要，从而实现了喹啉和吡啶配体的对映选择性。