N-(sec-butyl)-3-methoxyaniline | 31084-57-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(sec-butyl)-3-methoxyaniline
• 英文别名: N-(butan-2-yl)-3-methoxyaniline；N-butan-2-yl-3-methoxyaniline
• CAS: 31084-57-8
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: KKZIEMDVGFASBI-UHFFFAOYSA-N

物化性质

• 沸点：
  282.5±23.0 °C(Predicted)
• 密度：
  0.980±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  仲丁胺 、 3-氯苯甲醚 在 [(CyPF-tBu)PdCl2] 、 sodium t-butanolate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 24.0h， 以75%的产率得到N-(sec-butyl)-3-methoxyaniline
  参考文献：
  名称：

  [(CyPF-^tBu)PdCl₂]: An Air-Stable, One-Component, Highly Efficient Catalyst for Amination of Heteroaryl and Aryl Halides

  摘要：

  An air- and moisture-stable palladium catalyst, [(CyPF-Bu-t)PdCl2] (1), for coupling of heteroaryl chlorides, bromides, and iodides with a variety of primary amines is described. Most of these reactions occurred in high yield with 0.001-0.05 mol % catalyst loading. The reactions tolerated a wide range of functional groups.

  DOI：

  10.1021/ol801615u

文献信息

• Scope and Mechanism of the Ruthenium-Catalyzed Deaminative Coupling Reaction of Enones with Amines via Regioselective C_α–C_β Bond Cleavage
  作者：Dulanjali S. Thennakoon、Marat R. Talipov、Chae S. Yi

  DOI：10.1021/acs.organomet.3c00321

  日期：2023.10.9

  A highly regioselective C–C bond cleavage method of enones has been devised from the ruthenium-catalyzed deaminative coupling reaction with simple amines. The analogous catalytic coupling reaction of enones with anilines has led to a regioselective Cα–Cβ bond cleavage of enones in forming N-alkylanilines and 2,4-disubstituted quinolines. The reaction profile study showed the formation of a β-aminoimine

  通过钌催化的与简单胺的脱氨偶联反应，设计了烯酮的高度区域选择性 C-C 键断裂方法。烯酮与苯胺的类似催化偶联反应导致烯酮的区域选择性C α -C β键断裂，形成N-烷基苯胺和2,4-二取代喹啉。反应曲线研究表明，在 C-C 裂解产物形成之前，先形成了 β-氨基亚胺中间体。( E )-2-辛烯-4-酮与一系列对位反应的哈米特图-取代的苄胺通过给电子基团建立了强大的促进作用（ρ = -0.77 ± 0.1）。在产物的α-碳上观察到最显着的碳动力学同位素效应（C α = 1.018）。DFT 计算揭示了通过连续的 C-H 活化和 C-C 裂解步骤，然后是烯胺到亚胺重排和水解步骤的偶联反应的详细机制。该催化方法结合了氢借用和脱氨偶联策略，为烯酮提供了通用的 C α -C β键断裂方案。
• Simple, Efficient Catalyst System for the Palladium-Catalyzed Amination of Aryl Chlorides, Bromides, and Triflates
  作者：John P. Wolfe、Hiroshi Tomori、Joseph P. Sadighi、Jingjun Yin、Stephen L. Buchwald

  DOI：10.1021/jo991699y

  日期：2000.2.1

  Palladium complexes supported by (o-biphenyl)P(t-Bu)(2) (3) or (o-biphenyl)PCy2 (4) are efficient catalysts for the catalytic amination of a wide variety of aryl halides and triflates. Use of ligand 3 allows for the room-temperature catalytic amination of many aryl chloride, bromide, and triflate substrates, while ligand 4 is effective for the amination of functionalized substrates or reactions of acyclic secondary amines. The catalysts perform well for a large number of different substrate combinations at 80-110 degrees C, including chloropyridines and functionalized aryl halides and triflates using 0.5-1.0 mol % Pd; some reactions proceed efficiently at low catalyst levels (0.05 mol % Pd). These ligands are effective for almost all substrate combinations that have been previously reported with various other ligands, and they represent the most generally effective catalyst system reported to date. Ligands 3 and 4 are air-stable, crystalline solids that are commercially available. Their effectiveness is believed to be due to a combination of steric and electronic properties that promote oxidative addition, Pd-N bond formation, and reductive elimination.
• [(CyPF-^<i>t</i>Bu)PdCl₂]: An Air-Stable, One-Component, Highly Efficient Catalyst for Amination of Heteroaryl and Aryl Halides
  作者：Qilong Shen、John F. Hartwig

  DOI：10.1021/ol801615u

  日期：2008.9.18

  An air- and moisture-stable palladium catalyst, [(CyPF-Bu-t)PdCl2] (1), for coupling of heteroaryl chlorides, bromides, and iodides with a variety of primary amines is described. Most of these reactions occurred in high yield with 0.001-0.05 mol % catalyst loading. The reactions tolerated a wide range of functional groups.
• Benzene, Pyridine, and Pyridazine Derivatives
  申请人：Esanex, Inc.

  公开号：US20200071308A1

  公开（公告）日：2020-03-05

  Disclosed are compounds and pharmaceutically acceptable salts of Formula I wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , n, Q 1 , Q 2 , Q 3 , Y, and X 1 -X 4 are as defined herein. Compounds of Formula I are useful in the treatment of diseases and/or conditions related to cell proliferation, such as cancer, inflammation, arthritis, angiogenesis, or the like. Also disclosed are pharmaceutical compositions comprising compounds of the invention and methods of treating the aforementioned conditions using such compounds.
• A Comparative Reactivity Survey of Some Prominent Bisphosphine Nickel(II) Precatalysts in C–N Cross-Coupling
  作者：Jillian S. K. Clark、Christopher M. Lavoie、Preston M. MacQueen、Michael J. Ferguson、Mark Stradiotto

  DOI：10.1021/acs.organomet.6b00650

  日期：2016.9.26

  The synthesis and characterization of the new air-stable precatalyst (L1)Ni(o-tol)Cl (Cl; where L1 = JosiPhos CyPF-Cy) is reported, along with the results of a comparative reactivity survey involving Cl and analogous PAd-DalPhos- and DPPF-containing precatalysts (C2 and C3, respectively) in representative nickel-catalyzed C(sp(2))-N cross-coupling reactions. Precatalyst C1 was found to be competitive with, and in some cases complementary to, C2 in the monoarylation of ammonia and primary alkylamines with (hetero)aryl chlorides, including in otherwise challenging room temperature transformations. (Pseudo)halide comparison studies involving the cross-coupling of furfurylamine at room temperature revealed that in contrast to C2 precatalyst Cl performs less effectively with aryl bromides. Whereas C3 was found to be ineffective for such transformations, this DPPF-derived precatalyst proved superior to C1 and C2 in reactions involving the secondary dialkylamine test substrate morpholine.