N-sec-butyl-aniline | 881008-34-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-sec-butyl-aniline
• 英文别名: N-(1-methylpropyl)-aniline；N-sec-Butyl-anilin；N-s-butylaniline；N-sek.-Butyl-anilin；N-sec-Butylaniline；N-butan-2-ylaniline
• CAS: 881008-34-0
• 化学式: C₁₀H₁₅N
• 分子量: 149.236
• InChiKey: LAMTXWQPHWUMLX-UHFFFAOYSA-N

物化性质

• 沸点：
  225.0±0.0 °C(Predicted)
• 密度：
  0.939±0.06 g/cm3(Predicted)
• 保留指数：
  1223.2

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-sec-butyl-aniline 在 盐酸 、 alkali nitrite 作用下， 生成 N-sec-butyl-N-nitroso-aniline
  参考文献：
  名称：

  Reilly; Hickinbottom, Journal of the Chemical Society, 1920, vol. 117, p. 133

  摘要：

  DOI：
• 作为产物：
  描述：

  过氧化苯甲酰 在 potassium hydrogenphosphate trihydrate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N-sec-butyl-aniline
  参考文献：
  名称：

  Transition-Metal-Free Electrophilic Amination of Arylboroxines

  摘要：

  A transition-metal-free strategy to construct C(sp(2))-N bonds using arylboroxines and O-benzoyl hydroxylamines as coupling partners has been developed. This transformation provides a useful method to access various aromatic amines.

  DOI：

  10.1021/ol301912a

文献信息

• A Highly Active PN³ Manganese Pincer Complex Performing N-Alkylation of Amines under Mild Conditions
  作者：Leonard Homberg、Alexander Roller、Kai C. Hultzsch

  DOI：10.1021/acs.orglett.9b00832

  日期：2019.5.3

  on a nonsymmetric PN3-ligand scaffold for the N-alkylation of amines with alcohols utilizing the borrowing hydrogen methodology is reported. A broad range of anilines and the more challenging aliphatic amines were alkylated with primary and secondary alcohols. Moreover, the combination of low catalyst loadings and mild reaction conditions provides high efficiency for this atom-economic transformation

  报道了一种基于非对称PN 3-配体骨架的高活性Mn（I）催化剂，用于利用借位氢方法将胺与醇进行N-烷基化。各种苯胺和更具挑战性的脂肪胺都被伯醇和仲醇烷基化。此外，低催化剂装载量和温和的反应条件的结合为这种原子经济转化提供了高效率。
• Practical and regioselective amination of arenes using alkyl amines
  作者：Alessandro Ruffoni、Fabio Juliá、Thomas D. Svejstrup、Alastair J. McMillan、James J. Douglas、Daniele Leonori

  DOI：10.1038/s41557-019-0254-5

  日期：2019.5

  these molecules are assembled through the stepwise introduction of a reactivity handle in place of an aromatic C-H bond (that is, a nitro group, halogen or boronic acid) and a subsequent functionalization or cross-coupling. Here we show that aromatic amines can be constructed by direct reaction of arenes and alkyl amines using photocatalysis, without the need for pre-functionalization. The process

  用于制备芳香胺的碳-氮键的形成是全球范围内为生产高价值材料而进行的前五项反应之一，从原料化学品到药物和聚合物不等。由于这种普遍性和多样性，其制备方法影响了学术界和工业界的整个化学合成过程。通常，这些分子是通过逐步引入反应性手柄代替芳香族CH键（即硝基，卤素或硼酸）和随后的功能化或交叉偶联而组装而成的。在这里，我们表明，芳烃胺可以使用光催化作用，通过芳烃和烷基胺的直接反应来构建，而无需进行预功能化。该过程可以轻松准备高级构建基块，容忍的功能范围很广，并且可以通过批处理流协议来实现多克规模。通过对几种药物，农药，肽，手性催化剂，聚合物和有机金属配合物的修饰，证明了该策略作为后期功能化平台的优点。
• Direct reductive amination of carbonyl compounds using bis(triphenylphosphine) copper(I) tetrahydroborate
  作者：Mayur J. Bhanushali、Nitin S. Nandurkar、Malhari D. Bhor、Bhalchandra M. Bhanage

  DOI：10.1016/j.tetlet.2006.12.037

  日期：2007.2

  A direct reductive amination protocol for aldehydes/ketones using bis(triphenylphosphine) copper(I) tetrahydroborate as a novel reducing agent in the presence of sulfamic acid has been developed. The reagent chemoselectively reduces the imine moiety and does not affect other reducible functionalities such as chloro, nitro, cyano and methoxy.

  已经开发了在氨基磺酸存在下使用双（三苯基膦）四氢硼酸铜（I）作为新型还原剂的醛/酮直接还原胺化方案。该试剂化学选择性地还原亚胺部分，并且不影响其他可还原的官能团，例如氯，硝基，氰基和甲氧基。
• Direct reductive amination of carbonyl compounds with primary/secondary amines using recyclable water-soluble FeII/EDTA complex as catalyst
  作者：Malhari D. Bhor、Mayur J. Bhanushali、Nitin S. Nandurkar、Bhalchandra M. Bhanage

  DOI：10.1016/j.tetlet.2007.12.023

  日期：2008.2

  Direct reductive amination of aliphatic, aromatic and heterocyclic carbonyl compounds with primary/secondary amines is reported with water-soluble FeII/EDTA complex as a catalyst using low-pressure molecular hydrogen in a biphasic media. The catalyst is highly selective, recyclable and is an excellent replacement for expensive noble metal catalysts or stoichiometric reducing agents.

  据报道，水溶性Fe II / EDTA络合物作为催化剂，使用低压分子氢在双相介质中，将伯，仲胺直接与脂肪族，芳香族和杂环羰基化合物进行还原性胺化反应。该催化剂具有高选择性，可回收利用，是昂贵的贵金属催化剂或化学计量还原剂的理想替代品。
• Facile and efficient reductive N-alkylation of nitrobenzenes with alcohols catalyzed by Cu–Cr/γ-Al2O3
  作者：Ge Song、Jun Tian、Ligong Chen、Yang Li

  DOI：10.1007/s11164-014-1641-6

  日期：2015.8

  A facile and efficient method for reductive N-alkylation of nitrobenzenes with alcohols catalyzed by the bimetallic catalyst Cu30Cr5/γ-Al2O3, in a fixed-bed reactor, was successfully established. X-ray diffraction, temperature-programmed reduction, and X-ray photoelectron spectroscopy were used to characterize the catalyst. Introduction of Cr to Cu30/γ-Al2O3 was found to substantially enhance the dispersion of Cu0 particles, which are believed to be the active sites for the reductive N-alkylation. The reaction conditions were optimized and a series of alcohols and nitrobenzenes were converted into N-alkylated anilines in more than 90 % yield by use of this catalyst.

  成功建立了一种简便高效的方法，通过双金属催化剂Cu30Cr5/γ-Al2O3在固定床反应器中，用醇还原烷基化亚硝基苯。采用X射线衍射、温度程序还原和X射线光电子能谱对催化剂进行了表征。研究发现，将Cr引入Cu30/γ-Al2O3显著增强了Cu0颗粒的分散性，而Cu0颗粒被认为是还原烷基化反应的活性位点。对反应条件进行了优化，使用该催化剂将一系列醇和亚硝基苯转化为N-烷基化的苯胺，产率超过90%。