N-Ts-4-methyl-2-(4'-methylphenyl)aniline | 1312448-02-4

• 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-Ts-4-methyl-2-(4'-methylphenyl)aniline
• 英文别名: 4-methyl-N-[4-methyl-2-(4-methylphenyl)phenyl]benzenesulfonamide
• CAS: 1312448-02-4
• 化学式: C₂₁H₂₁NO₂S
• 分子量: 351.469
• InChiKey: JTATVGRCWHDHOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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-Ts-4-methyl-2-(4'-methylphenyl)aniline 在 Oxone 、 palladium diacetate 、 对甲苯磺酸 、 三甲基乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以84%的产率得到2,6-dimethyl-9-Ts-9H-carbazole
  参考文献：
  名称：

  Pd-Catalyzed Intramolecular Oxidative C–H Amination: Synthesis of Carbazoles

  摘要：

  A Pd-catalyzed oxidative C-H amination of N-Ts-2-arylanilines under ambient temperature using Ozone as an inexpensive, safe, and easy-to-handle oxidant has been developed. This process represents a green and practical method for the facile construction of carbazoles with a broad substrate scope and wide functional group tolerance.

  DOI：

  10.1021/ol201416u
• 作为产物：
  描述：

  4-甲苯硼酸 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 N-Ts-4-methyl-2-(4'-methylphenyl)aniline
  参考文献：
  名称：

  Palladium-Catalyzed Oxidative Insertion of Carbon Monoxide to N-Sulfonyl-2-aminobiaryls through C–H Bond Activation: Access to Bioactive Phenanthridinone Derivatives in One Pot

  摘要：

  Palladium-catalyzed oxidative carbonylation of N-sulfonyl-2-aminobiaryls through C-H bond activation and C-C, C-N bond formation under TFA-free and milder conditions has been developed. The reaction tolerates a variety of substrates and provides biologically important phenanthrldlnone derivatives in yields up to 94%.

  DOI：

  10.1021/ol4001922

文献信息

• Transition-metal-free synthesis of aromatic amines via the reaction of benzynes with isocyanates
  作者：Jeong Hoon Seo、Haye Min Ko

  DOI：10.1016/j.tetlet.2018.01.022

  日期：2018.2

  unexpected reaction between benzynes and isocyanates to generate aromatic amines has been developed under transition-metal-free conditions. The in situ prepared anions formed through cleavage of the NC bond in isocyanates, reacted with aryne precursors to afford various aniline derivatives in moderate to excellent yield and tolerated various substituents on the o-silyl aryl triflate and the isocyanate.

  在不含过渡金属的条件下，苯并炔与异氰酸酯发生意外反应生成芳族胺。在原位制备过N开裂而形成的阴离子C键中的异氰酸酯，具有芳炔前体在中等至良好的产率反应，得到各种苯胺衍生物和耐受上各种取代基ø -甲硅烷基三氟甲磺酸的芳基和异氰酸酯。
• Pd-Catalyzed Sequential CC and CN Bond Formations for the Synthesis of N-Heterocycles: Exploiting Protecting Group-Directed CH Activation under Modified Reaction Conditions
  作者：Byung Seok Kim、Sun Young Lee、So Won Youn

  DOI：10.1002/asia.201100024

  日期：2011.8.1

  addition reaction of N‐Ts‐2‐arylanilines with activated olefins has been achieved at ambient temperature under the newly defined reaction conditions. This process highlighted the directing effect of the N‐protecting group in CH activation, displayed broad substrate scope with wide functional group compatibility; thus rendering a straightforward entry to a wide variety of N‐heterocycles such as d

  简便高效：在新定义的反应条件下，在环境温度下实现了N -Ts-2-芳基苯胺与活化烯烃的Pd催化多米诺烯化反应/共轭加成反应。该过程突出了N保护基在CH活化中的指导作用，显示了广泛的底物范围和广泛的官能团相容性。因此可以直接进入各种N杂环化合物，例如二氢菲啶。
• Palladium-Catalyzed Oxidative CC Bond Cleavage Cyclization of Biaryl-2-amines with Alkenes Involving CH Olefination and Carboamination
  作者：Yan-Yun Liu、Ren-Jie Song、Cui-Yan Wu、Lu-Bin Gong、Ming Hu、Zhi-Qiang Wang、Ye-Xiang Xie、Jin-Heng Li

  DOI：10.1002/adsc.201100651

  日期：2012.2

  A new, general method for the synthesis of phenanthridines has been developed by palladium-catalyzed oxidative remote CH olefination–carboamination–CC bond cleavage tandem reaction. It is noteworthy that alkenes are used as the one-carbon resources for this tandem reaction.

  通过钯催化的氧化远程CH烯化反应-碳氨化反应-CC键裂解串联反应，开发了一种新型的菲啶合成方法。值得注意的是，烯烃被用作该串联反应的单碳资源。