N,N-二丁基萘-1-胺 | 204126-63-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: N,N-二丁基萘-1-胺
• 英文名称: N,N-dibutyl-N-(1-naphthyl)amine
• 英文别名: N,N-dibutyl-1-naphthylamine；dibutyl-[1]naphthyl-amine；1-Dibutylamino-naphthalin；Dibutyl-[1]naphthyl-amin；1-Naphthalenamine, N,N-dibutyl-；N,N-dibutylnaphthalen-1-amine
• CAS: 204126-63-6
• 化学式: C₁₈H₂₅N
• 分子量: 255.403
• InChiKey: MZAAHJYILRAGET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-二丁基萘-1-胺 在 正丁基锂 、 四溴环己二烯-1-酮 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 生成 1-(4-Dibutylamino-naphthalen-1-yl)-2-hydroxy-2-methyl-propan-1-one
  参考文献：
  名称：

  The influence of tetrahydroquinoline rings in dicyanomethylenedihydrofuran (DCDHF) single-molecule fluorophores

  摘要：

  We have synthesized several series of DCDHF fluorophores with the amine donor either acyclic or constrained in one or two tetrahydroquinoline rings. The absorption and the fluorescence emission wavelengths and quantum yields have been determined and correlated with the specific donor structures. Generally, inclusion of the donor in a ring annulated to the benzene or naphthalene aromatic (Ar) pi-core results in a bathochromic shift of absorption and emission accompanied by an increase in the quantum yield. Thus, the tetrahydroquinoline donor provides an efficient way to tailor the properties of fluorophores with substituted amines as electron-donating groups. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.10.044
• 作为产物：
  描述：

  二正丁胺 、 1-氯萘 在 (SIPr)Pd(cinnanmyl)Cl 、 potassium tert-butylate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 1.0h， 以95%的产率得到N,N-二丁基萘-1-胺
  参考文献：
  名称：

  用于室温 Suzuki-Miyaura 和 Buchwald-Hartwig 反应的改性 (NHC)Pd(allyl)Cl (NHC = N-杂环卡宾) 配合物

  摘要：

  一系列 (NHC)Pd(R-烯丙基)Cl 配合物 [NHC: IPr = N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene, SIPr = N,N'-bis(2,6 -二异丙基苯基)-4,5-二氢咪唑-2-亚基；R = H, Me, gem-Me2, Ph] 已被合成并充分表征。与 (NHC)Pd(烯丙基)Cl 相比，烯丙基支架末端位置的取代有利于更容易的活化步骤。这在 Suzuki-Miyaura 和 Buchwald-Hartwig 反应中转化为更高的催化活性，允许在室温下在几分钟内偶联未活化的芳基氯化物。在 Suzuki-Miyaura 反应中，芳基三氟甲磺酸酯、溴化物和氯化物使用非常低的催化剂负载量与硼酸反应。在N-芳基胺化反应中，广泛的底物得到了有效偶联；伯-, 仲-, 烷基-, 或芳基胺与未活化、中性和活化的芳基氯化物和溴化物以

  DOI：

  10.1021/ja057704z

文献信息

• Palladium-Catalysed Amination of Aryl- and Heteroaryl Halides Using<i>tert</i>-Butyl Tetraisopropylphosphorodiamidite as an Easily Accessible and Air-Stable Ligand
  作者：Gheorghe-Doru Roiban、Gerlinde Mehler、Manfred T. Reetz

  DOI：10.1002/ejoc.201301789

  日期：2014.4

  phosphorus compound tert-butyl tetraisopropylphosphorodiamidite, prepared from bis(diisopropylamino)chlorophosphine, is an excellent ligand for palladium-catalysed Buchwald–Hartwig amination of aryl- and heteroaryl chlorides and bromides. Based on its ready accessibility and air-stability, this amination protocol is a practical approach to the synthesis of industrially important aryl- and heteroarylamines.

  由双（二异丙基氨基）氯膦制备的磷化合物叔丁基四异丙基磷酰胺是钯催化的芳基和杂芳基氯化物和溴化物的 Buchwald-Hartwig 胺化的极好配体。基于其易于使用和空气稳定性，该胺化方案是合成工业上重要的芳基胺和杂芳基胺的实用方法。
• Epoxy-based polymer bearing 1-naphthylamine units: highly selective fluorescent chemosensor for ferric ion
  作者：Samaresh Ghosh、Chandan K. Dey、Rajkumar Manna

  DOI：10.1016/j.tetlet.2010.04.016

  日期：2010.6

  simple epoxy-based polymer 1 bearing 1-naphthylamine units has been synthesized and its recognition behaviors toward various metal ions have been investigated in THF–water (8:2, v/v) solution. The designed polymer 1 was found to exhibit selective ON–OFF-type fluorosensing behavior toward Fe3+ ions over other representative metal ions such as Cu2+, Zn2+, Co2+, Ni2+, and Hg2+ ions.

  已经合成了带有1-萘胺单元的简单的基于环氧的聚合物1，并且已经在THF-水（8：2，v / v）溶液中研究了其对各种金属离子的识别行为。所设计的聚合物1，发现显示出选择性ON-OFF型fluorosensing行为朝向的Fe 3+相对于其他代表金属离子如Cu离子2+，锌2+，钴2+，镍2+ ，和Hg 2+离子。
• Chemoselective synthesis of tertiary and secondary amines by reductive amination of aldehydes
  作者：Wan-Jin Xiong、Lei Li、Jiang-Tao Li、Shi-Qiang Zhang、Jun-Lei Tang、Taigang Zhou

  DOI：10.1016/j.tetlet.2023.154684

  日期：2023.9

  A simple and efficient catalyst-free chemoselective reductive amination of primary amines and aldehydes to synthesis of tertiary and secondary amines with borane complex was developed. Primary amines are converted into tertiary and secondary amines in one pot reaction under mild condition with good functional group compatibility and It does not require any catalyst to participate in this reaction.

  开发了一种简单高效的无催化剂化学选择性还原胺化伯胺和醛，以与硼烷配合物合成叔胺和仲胺。伯胺转化为叔胺和仲胺的一锅反应条件温和，官能团相容性好，并且不需要任何催化剂参与该反应。通过改变硼烷络合物的空间位阻来实现化学选择性控制。该策略成功应用于合成丁卡因（麻醉剂），并通过同位素标记实验验证了其潜在机制。
• Aromatic C(sp²)−H Functionalization by Consecutive Paired Electrolysis: Dibromination of Aryl Amines with Dibromoethane at Room Temperature
  作者：Gaurav Shukla、Malkeet Singh、Anup Kumar Yadav、Maya Shankar Singh

  DOI：10.1002/chem.202303179

  日期：2024.2.12

  Herein, we disclose a facile and efficient electrochemical method for the dibromination of aryl amines by double functionalization of aromatic C(sp²)−H (both para and ortho) under metal‐ and external oxidant‐free conditions at room temperature for the first time. The reaction is demonstrated using 1,2‐dibromoethane to dibrominate a wide range of N‐substituted aryl amines in a simple setup with C(+)/Pt(−) electrodes under mild reaction conditions. This transformation proceeds smoothly with a broad substrate scope affording the valuable and versatile N‐substituted 2,4‐dibromoanilines in moderate to excellent yields with high regioselectivity. In this paired electrolysis, cathodic reduction of 1,2‐DBE followed by anodic oxidation generates bromonium intermediates, which then couple with anilines to furnish the dibrominated products. It represents a distinctive approach to challenging redox‐neutral reactions. The versatility of the electrochemical ortho‐, para‐dibromination was reflected by unique regioselectivities for challenging aryl amines and gram‐scale electrosynthesis without the use of a stoichiometric oxidant or an activating agent.

  摘要在此，我们首次公开了一种在室温无金属和外部氧化剂条件下，通过芳香族 C(sp2)-H（对位和正位）双官能化二溴化芳基胺的简便高效的电化学方法。该反应使用 1,2-二溴乙烷进行演示，在温和的反应条件下，通过使用 C(+)/Pt(-) 电极的简单设置，对多种 N 取代芳胺进行二溴化处理。这一转化过程进展顺利，底物范围广泛，能以中等到极好的产率和高区域选择性获得有价值的多用途 N-取代型 2,4-二溴苯胺。在这种配对电解过程中，1,2-DBE 阴极还原后阳极氧化生成溴鎓中间体，然后与苯胺偶联生成二溴化合产物。这是一种具有挑战性的氧化还原中性反应的独特方法。电化学正、对二溴化反应的多功能性体现在对具有挑战性的芳基胺具有独特的区域选择性，以及无需使用化学氧化剂或活化剂即可进行克级规模的电合成。
• Voronin; Nasibulin; Klyuyev, Petroleum Chemistry, 1997, vol. 37, # 6, p. 508 - 514
  作者：Voronin、Nasibulin、Klyuyev

  DOI：——

  日期：——