4-methyl-2-(naphthalen-1-yl)aniline | 1183962-77-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-methyl-2-(naphthalen-1-yl)aniline
• 英文别名: 4-Methyl-2-(naphthalen-1-yl) aniline；4-methyl-2-naphthalen-1-ylaniline
• CAS: 1183962-77-7
• 化学式: C₁₇H₁₅N
• mdl: MFCD12859560
• 分子量: 233.313
• InChiKey: BBUXENRMQDKNFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.058
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-methyl-2-(naphthalen-1-yl)aniline 在 吡啶 、 silver(I) acetate 、 palladium diacetate 作用下， 以 乙腈 为溶剂， 反应 26.0h， 生成 2-methyl-5-tosylbenzo[k]phenanthridin-6(5H)-one
  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
• 作为产物：
  描述：

  2-溴-4-甲基苯胺 、 1-萘硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 生成 4-methyl-2-(naphthalen-1-yl)aniline
  参考文献：
  名称：

  PdII催化的游离胺导向的Atroposelective CH Olefination合成轴向手性联芳基-2-胺。

  摘要：

  一个简单且普遍存在的基团，即游离胺，被用作通过PdII催化的对映选择性CH烯化反应合成轴向手性联芳基化合物的导向基团。可以以高收率和高对映选择性（高达97％ee）获得多种轴向手性联芳基-2-胺。手性螺环磷酸（SPA）被证明是一种有效的配体，在克级合成中，对映体的控制不会降低其负载量至1 mol％。所得的轴向手性联芳基-2-胺也为合成一组手性配体提供了平台。

  DOI：

  10.1002/anie.201915674

文献信息

• Palladium-Catalyzed C–H Bond Activation by Using Iminoquinone as a Directing Group and an Internal Oxidant or a Co-oxidant: Production of Dihydrophenanthridines, Phenanthridines, and Carbazoles
  作者：Selvam Raju、Pratheepkumar Annamalai、Pei-Ling Chen、Yi-Hung Liu、Shih-Ching Chuang

  DOI：10.1021/acs.orglett.7b01956

  日期：2017.8.4

  A palladium-catalyzed C–H bond activation reaction, via a redox-neutral pathway, for the preparation of dihydrophenanthridine, phenanthridine, and carbazole derivatives from biaryl 2-iminoquinones is developed. The preinstalled iminoquinone was designed to act as a directing group for ortho C–H activation and an internal oxidant or a co-oxidant. This catalysis proceeded through the following sequence:

  通过氧化还原中性途径开发了钯催化的CH键活化反应，用于从联芳基2-亚氨基醌制备二氢菲啶，菲啶和咔唑衍生物。预先安装的亚氨基醌被设计成可作为邻位C–H活化的引导基团和内部氧化剂或助氧化剂。该催化过程按以下顺序进行：C–H键活化，活化烯烃的配位和插入，β-氢化物消除，H-移位，插入和质子化或β-氢化物消除。另外，通过使用该方法可以有效地制备咔唑，而无需添加外部氧化剂。
• Palladium(II)-Catalyzed Mono- and Bis-alkenylation of <i>N</i>-Acetyl-2-aminobiaryls through Regioselective C–H Bond Activation
  作者：Pratheepkumar Annamalai、Kou-Chi Hsu、Selvam Raju、Huan-Chang Hsiao、Chih-Wei Chou、Gu-Ying Lin、Cheng-Ming Hsieh、Pei-Ling Chen、Yi-Hung Liu、Shih-Ching Chuang

  DOI：10.1021/acs.joc.8b00194

  日期：2018.4.6

  We developed palladium-catalyzed oxidative coupling of olefins with N-acyl 2-aminobiaryls through a sequence of ortho C–H bond activation/alkene insertion/reductive elimination. Furthermore, we controlled the selectivity of mono- and bis-alkenylation products with the solvent effect. The developed protocol was promising for a broad substrate scope ranging from activated olefins with a wide variety

  我们通过一系列邻位碳氢键活化/烯烃插入/还原消除的过程，开发了钯与N-酰基2-氨基联芳基的钯催化氧化偶联反应。此外，我们通过溶剂效应控制了单链和双链烯基化产物的选择性。所开发的方案有望在从具有各种官能团的活化烯烃到未活化烯烃的广泛底物范围内进行。
• Synthesis, Isolation, and Characterization of Mono- and Bis-norbornene-Annulated Biarylamines through Pseudo-Catellani Intermediates
  作者：Pratheepkumar Annamalai、Huan-Chang Hsiao、Selvam Raju、Yi-Hsuan Fu、Pei-Ling Chen、Jia-Cherng Horng、Yi-Hung Liu、Shih-Ching Chuang

  DOI：10.1021/acs.orglett.9b00119

  日期：2019.2.15

  A palladium-catalyzed C–H functionalization of an external ring of N-acyl 2-aminobiaryl with bicyclo[2.2.1]hept-2-ene (norbornene) via multiple C–H bond activations was developed. This study is the first report of the formation of bis-norbornene annulated biarylamines isomers (syn-3a′/anti-3a′ = 36:64) from multiple C–H bond functionalizations. Additionally, nondirected C–H bond functionalization at

  通过多个CH键活化，开发了钯催化的N-酰基2-氨基联芳与双环[2.2.1]庚-2-烯（降冰片烯）外环的CH功能化。这项研究是第一个关于由多个C–H键官能化形成双降冰片烯环化的联芳基胺异构体（syn - 3a' / anti - 3a' = 36:64）的报道。此外，在C-4'位置用烯烃进行的无方向C–H键官能化可完全形成五个C–H键的C–H功能化，从而形成一个稳定的六取代苯环。
• Iptycenes with an acridinone motif developed through [4+2] cycloaddition of tethered naphthalene and iminoquinone via a radical reaction
  作者：Selvam Raju、Pratheepkumar Annamalai、Pei-Ling Chen、Yi-Hung Liu、Shih-Ching Chuang

  DOI：10.1039/c7cc03030d

  日期：——

  2-(naphthalen-1-yl)anilines and p-benzoquinones through copper (II)-mediated radical cyclisation. This unusual cyclisation reaction resulted in the robust and efficient syntheses of iptycenes with an acridinone motif. These iptycenes can be further transformed to planar acridinone heterocyclics through the Diels–Alder reaction.

  通过铜（II）介导的自由基环化作用，将2-（萘-1-基）苯胺和对苯醌组合在一起，从而开发出一类新的茂钛。这种不寻常的环化反应导致了带有an啶酮基序的iptycenes的稳健而高效的合成。通过狄尔斯-阿尔德反应，这些iptycenes可以进一步转化为平面的cri啶酮杂环。
• Preparation of phenanthrenes from ortho-amino-biphenyls and alkynes via base-promoted homolytic aromatic substitution
  作者：Marcel Hartmann、Constantin Gabriel Daniliuc、Armido Studer

  DOI：10.1039/c4cc10063h

  日期：——

  transition-metal-free phenanthrene synthesis starting from readily accessible ortho-amino-biaryls is presented. The biarylamines are in situ transformed into the corresponding diazonium salts which upon single electron reduction give the corresponding aryl radicals. Addition to an alkyne and subsequent base promoted homolytic aromatic substitution (BHAS) provide phenanthrenes in moderate to good yields

  提出了从容易获得的邻氨基联芳基开始的无过渡金属菲的合成。将联芳基胺原位转化为相应的重氮盐，其在单电子还原时得到相应的芳基。加成炔烃和随后的碱促进的均溶芳族取代（BHAS）提供了中等至良好产率的菲。