N-2-pyridyl-2-aminooctane | 1301628-38-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-2-pyridyl-2-aminooctane
• 英文别名: N-(octan-2-yl)pyridin-2-amine；N-octan-2-ylpyridin-2-amine
• CAS: 1301628-38-5
• 化学式: C₁₃H₂₂N₂
• 分子量: 206.331
• InChiKey: BVFXRGHTQNISAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 、 仲辛醇 在 1,2-双(二苯基膦)乙烷 、 palladium dichloride 、 lithium hydroxide 作用下， 以 neat (no solvent) 为溶剂， 反应 24.0h， 以68%的产率得到N-2-pyridyl-2-aminooctane
  参考文献：
  名称：

  使用伯醇和仲醇高效地催化钯催化的胺的N-烷基化

  摘要：

  发现在dppe或Xantphos（t -Bu）作为配体的情况下，PdCl 2是使用伯醇在90-130°C的纯净条件下对各种伯和环状仲胺进行N-烷基化的有效催化剂。有趣的是，在130–150°C下使用更具挑战性的仲醇作为烷基化剂时，获得了良好的优良收率。如10毫摩尔规模所示，TON值为900时，收率可高达90％，证明该反应可以轻松扩大规模。

  DOI：

  10.1021/cs400799n

文献信息

• N-Alkylation of poor nucleophilic amines and derivatives with alcohols by a hydrogen autotransfer process catalyzed by copper(II) acetate: scope and mechanistic considerations
  作者：Ana Martínez-Asencio、Diego J. Ramón、Miguel Yus

  DOI：10.1016/j.tet.2011.02.075

  日期：2011.4

  simple catalyst for the selective N-monoalkylation of amino derivatives with poor nucleophilic character, such as aromatic and heteroaromatic amines as well as carboxamides, phosphinamides, sulfonamides, and phosphazenes, using in all cases primary alcohols as initial source of the electrophiles, through a hydrogen autotransfer process. In the case of sulfonamides, the monoalkylation process followed

  乙酸铜（II）是一种通用，廉价且简单的催化剂，用于对亲核性较差的氨基衍生物（例如芳族和杂芳族胺以及羧酰胺，次膦酰胺，磺酰胺和磷腈）进行选择性N-单烷基化，在所有情况下均使用伯通过氢自动转移过程，将醇作为亲电试剂的初始来源。在磺酰胺的情况下，单烷基化过程随后是萘催化的还原性脱保护得到伯胺，这是氨直接单烷基化的间接替代方法。使用氘标记试剂对反应进行了研究，表明脱氢和氢化步骤不在同一铜原子配位球上进行，
• Efficient catalytic aryl amination of bromoarenes using 3-iminophosphine palladium(II) chloride
  作者：Danielle C. Samblanet、Joseph A.R. Schmidt

  DOI：10.1016/j.jorganchem.2012.08.027

  日期：2012.12

  While pursuing the development of new hydroamination catalysts, a 3-iminophosphine palladium(II) chloride complex [(3IP)PdCl2] was synthesized that has subsequently proven to be an effective precatalyst for the aryl amination of bromoarenes. This (3IP)PdCl2 complex has been utilized in the catalytic aryl amination of both bromobenzene and bromopyridine derivatives, specifically yielding excellent activity in coupling reactions involving bromobenzene, 4-bromotoluene, and 2-bromopyridine. Using a standard set of catalytic conditions, many alkyl and aryl amines have been investigated as coupling partners in the aryl amination of bromoarenes. In general, secondary alkyl amines and ortho-substituted anilines proved to be the best substrates for this reaction, commonly giving quantitative conversion to products, while primary amines and other anilines gave only poor to moderate results. Catalytic screening data, product yields, and full characterization of isolated products are included. (C) 2012 Elsevier B.V. All rights reserved.
• An Efficient Palladium-Catalyzed N-Alkylation of Amines Using Primary and Secondary Alcohols
  作者：Tuan Thanh Dang、Balamurugan Ramalingam、Siah Pei Shan、Abdul Majeed Seayad

  DOI：10.1021/cs400799n

  日期：2013.11.1

  PdCl2 in the presence of dppe or Xantphos(t-Bu) as the ligand is found to be an efficient catalyst for the N-alkylation of various primary and cyclic secondary amines using primary alcohols at 90–130 °C under neat conditions. Interestingly, good to excellent yields were achieved when more challenging secondary alcohols were used as alkylating agents at 130–150 °C. The reaction could be easily scaled

  发现在dppe或Xantphos（t -Bu）作为配体的情况下，PdCl 2是使用伯醇在90-130°C的纯净条件下对各种伯和环状仲胺进行N-烷基化的有效催化剂。有趣的是，在130–150°C下使用更具挑战性的仲醇作为烷基化剂时，获得了良好的优良收率。如10毫摩尔规模所示，TON值为900时，收率可高达90％，证明该反应可以轻松扩大规模。