4-methyl-N-((5-nitroquinolin-8-yl)methyl)benzenesulfonamide | 1575701-52-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-methyl-N-((5-nitroquinolin-8-yl)methyl)benzenesulfonamide
• 英文别名: 4-methyl-N-[(5-nitroquinolin-8-yl)methyl]benzenesulfonamide
• CAS: 1575701-52-8
• 化学式: C₁₇H₁₅N₃O₄S
• 分子量: 357.39
• InChiKey: QEYWLRQSZKBOCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氨基-4-硝基甲苯 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 硫酸 、 sodium iodide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 16.0h， 生成 4-methyl-N-((5-nitroquinolin-8-yl)methyl)benzenesulfonamide
  参考文献：
  名称：

  Rhodium(III)-Catalyzed Intermolecular Amidation with Azides via C(sp³)–H Functionalization

  摘要：

  The amidation reactions of 8-methylquinolines with azides catalyzed by a cationic rhodium(III) complex proceed efficiently to give quinolin-8-ylmethanamine derivatives in good yields via C(sp(3))-H bond activation under external oxidant-free conditions. A catalytically competent five-membered rhodacycle has been isolated and characterized, revealing a key intermediate in the catalytic cycle.

  DOI：

  10.1021/jo5008515

文献信息

• Ru(<scp>ii</scp>)-catalyzed amidation reactions of 8-methylquinolines with azides via C(sp³)–H activation
  作者：Bingxian Liu、Bin Li、Baiquan Wang

  DOI：10.1039/c5cc06230f

  日期：——

  The Ru(II)-catalyzed amidation reactions of 8-methylquinolines with azides have been developed. It is the first example of [(p-cymene)RuCl2]2-catalyzed C(sp3)-H bond intermolecular amidation reaction which give quinolin-8-ylmethanamines under mild reaction conditions...

  已经开发了Ru（II）催化的8-甲基喹啉与叠氮化物的酰胺化反应。这是[（对-异丙基）RuCl2] 2-催化的C（sp3）-H键分子间酰胺化反应的第一个例子，该反应在温和的反应条件下产生了喹啉-8-基甲胺。
• Rhodium(III)-catalyzed C(sp³)–H Amidation of 8-Methylquinolines with Amides at Room Temperature
  作者：Xiaolei Huang、Jingsong You

  DOI：10.1246/cl.150848

  日期：2015.12.5

  Here we disclose a Rh(III)-catalyzed chelation-assisted C(sp3)–H activation of 8-methylquinolines, which can enable intermolecular amidation using commercially available, reliable amides as the ami...

  在这里，我们公开了 8-甲基喹啉的 Rh(III) 催化螯合辅助 C(sp3)-H 活化，它可以使用市售可靠的酰胺作为酰胺实现分子间酰胺化。
• Iridium-Catalyzed Intermolecular Amidation of sp³ C–H Bonds: Late-Stage Functionalization of an Unactivated Methyl Group
  作者：Taek Kang、Youngchan Kim、Donggun Lee、Zhen Wang、Sukbok Chang

  DOI：10.1021/ja501014b

  日期：2014.3.19

  Reported herein is the iridium-catalyzed direct amidation of unactivated sp(3) C-H bonds. With sulfonyl and acyl azides as the amino source, the amidation occurs efficiently under mild conditions over a wide range of unactivated methyl groups with high functional group tolerance. This procedure can be successfully applied for the direct introduction of an amino group into complex compounds and thus can serve as a powerful synthetic tool for late-stage C-H functionalization.