N-phenethylnaphthalen-1-amine | 65021-64-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-phenethylnaphthalen-1-amine
• 英文别名: N-(2-Phenylethyl)naphthalen-1-amine
• CAS: 65021-64-9
• 化学式: C₁₈H₁₇N
• 分子量: 247.34
• InChiKey: GXSCPSMITCFJAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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-phenethylnaphthalen-1-amine 在 potassium carbonate 、 iron(III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.08h， 以73%的产率得到N,N'-bis(phenylethyl)-(1,1'-binaphthyl)-4,4'-diamine
  参考文献：
  名称：

  Iron(III)-Promoted Oxidative Coupling of Naphthylamines: Synthetic and Mechanistic Investigations

  摘要：

  A facile route to the synthesis of 1,1'-binaphthyl-4,4'-diamines (naphthidines) and 1,1'-binaphthyl-2,2'-diamines (BINAMs) was developed by the oxidative homocoupling of 1- and 2-naphthylamines, respectively, using FeCl(3) as oxidant and K(2)CO(3) as base in 1,2-dichloroethane under ambient conditions. A preliminary mechanistic investigation was performed by the ESR spectroscopy and intermediate-trapping technique.

  DOI：

  10.1021/ol202058r
• 作为产物：
  描述：

  Naphthalen-1-yl-[2-phenyl-eth-(E)-ylidene]-amine 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 N-phenethylnaphthalen-1-amine
  参考文献：
  名称：

  Intermolecular Hydroamination of Alkynes Catalyzed by Dimethyltitanocene

  摘要：

  DOI：

  10.1002/(sici)1521-3773(19991115)38:22<3389::aid-anie3389>3.0.co;2-e
• 作为试剂：
  描述：

  亚磷酸三苯酯 、 苯乙醇 、 1-萘胺 在 amine 、 alcohol 、 N-phenethylnaphthalen-1-amine 作用下， 以 水 为溶剂， 210.0~245.0 ℃ 、88.87 kPa 条件下， 反应 12.0h， 以210 parts of N-(2'-phenylethyl)-1-naphthylamine (85% of theory) are obtained的产率得到N-phenethylnaphthalen-1-amine
  参考文献：
  名称：

  Manufacture of arylamines

  摘要：

  芳胺是通过在磷-III化合物存在下，将醇与胺反应制造的。本发明制造的芳胺是农药、光亮剂，特别是氨基香豆素衍生物和染料，特别是苯氧基、吡罗林、罗丹明、噁唑、偶氮、三苯甲烷和二苯甲烷系列的中间体。

  公开号：

  US04067903A1

文献信息

• Mono/Dual Amination of Phenols with Amines in Water
  作者：Wanyi Liang、Feng Xie、Zhihai Yang、Zheng Zeng、Chuanjiang Xia、Yibiao Li、Zhongzhi Zhu、Xiuwen Chen

  DOI：10.1021/acs.orglett.0c02924

  日期：2020.11.6

  We herein describe a practical direct amination of phenols through a palladium-catalyzed hydrogen-transfer-mediated activation method to synthesize the secondary and tertiary amines. In this conversion, environmentally friendly water and inexpensive ammonium formate were used as solvent and reductant, respectively. A range of amines, including aliphatic amines, aniline, secondary amines, and diamines

  我们在本文中描述了通过钯催化的氢转移介导的活化方法对苯酚进行的实际直接胺化反应，以合成仲胺和叔胺。在这种转化中，分别将环保型水和廉价的甲酸铵用作溶剂和还原剂。多种胺，包括脂族胺，苯胺，仲胺和二胺，可以通过这种方法有效地偶联，以实现酚的单/双胺化和环化。这项研究不仅为合成仲和叔萘胺提供了绿色和温和的策略，而且扩大了有机化学中氯喹的合成。
• Enabling Reductive C–N Cross-Coupling of Nitroalkanes and Boronic Acids by Steric Design of P(III)/P(V)═O Catalysts
  作者：Gen Li、Yuzuru Kanda、Seung Youn Hong、Alexander T. Radosevich

  DOI：10.1021/jacs.2c01487

  日期：2022.5.11

  bond-forming reductive coupling of nitroalkanes with arylboronic acids and esters is reported. The method shows excellent chemoselectivity for the nitro/boronic acid substrate pair, allowing the synthesis of N-(hetero)arylamines rich in functionalization. The identification of a sterically reduced phosphetane catalyst capable of productive coupling in the P(III)/P(V)═O redox manifold is the key enabling development

  报道了硝基烷烃与芳基硼酸和酯的有机磷催化的 C-N 键形成还原偶联。该方法对硝基/硼酸底物对显示出优异的化学选择性，允许合成富含功能化的N -（杂）芳基胺。鉴定能够在 P(III)/P(V)=O 氧化还原歧管中进行有效偶联的空间还原磷杂环丁烷催化剂是实现发展的关键。结合实验动力学和计算机制研究表明，空间还原的催化剂影响后限速步骤，使 C-N 偶联事件优先于有害的旁路。
• Synthesis, photophysical characterisation and photostability studies of NIR probes with aliphatic, aromatic and chlorinated terminals in 5- and 9-amino positions of benzo[ a ]phenoxazines
  作者：B. Rama Raju、Marcello M.T. Carvalho、Maria Inês P.S. Leitão、Paulo J.G. Coutinho、M. Sameiro T. Gonçalves

  DOI：10.1016/j.dyepig.2016.04.049

  日期：2016.9

  m chlorides possessing mono and disubstituted amines with 3-chloropropyl groups at the 9-position, isopropyl, cyclohexyl and phenyl groups as terminals at 5-postion was synthesised. Photophysical studies were performed in dry ethanol and aqueous solutions. The terminals at the 5-amino position were found to influence the acid-base equilibrium. The presence of hydroxyl functionality at 2-position was

  一系列新的苯并[ a]合成了具有在9位上具有3-氯丙基，在5位上为末端的异丙基，环己基和苯基的单和二取代胺的]苯恶嗪氯化物。在无水乙醇和水溶液中进行光物理研究。发现5-氨基位置的末端影响酸碱平衡。发现2-位羟基官能团的存在引入了另一种碱性形式，该碱性形式与干燥乙醇溶液中的阳离子酸形式处于平衡状态。还研究了这些化合物在不同介质中的光稳定性，并在模型生物膜中观察到了对光漂白的高抵抗力。在蛋白质中，在1小时30分钟内会发生20％的中等光漂白，
• Rh(I)-Catalyzed Coupling of Azides with Boronic Acids Under Neutral Conditions
  作者：Shiyang Xu、Hong Guo、Yuhan Liu、Wenxu Chang、Jiyao Feng、Xiongkui He、Zhenhua Zhang

  DOI：10.1021/acs.orglett.2c02053

  日期：2022.8.5

  importance of polyfunctional amines, C–N bond formation is important in synthetic organic chemistry. Here we present a neutral amination reaction using azides as the nitrogen source and arylboronic acids with a rhodium(I) catalyst to afford alkyl–aryl and aryl–aryl secondary amines. Natural products and pharmaceutical derivatives were applied, and gram-scale reactions were performed, which demonstrated the

  由于多官能胺的重要性，C-N 键的形成在合成有机化学中很重要。在这里，我们提出了使用叠氮化物作为氮源和芳基硼酸与铑 (I) 催化剂的中性胺化反应，得到烷基-芳基和芳基-芳基仲胺。应用了天然产物和药物衍生物，并进行了克级反应，证明了其效用。机械实验和 DFT 计算表明该反应涉及金属-氮烯中间体。
• Pyrolysis/GC/MS Analysis of <i>N</i>-(1-Deoxy-<scp>d</scp>-fructos-1-yl)-<scp>l</scp>-phenylalanine:  Identification of Novel Pyridine and Naphthalene Derivatives
  作者：Anahita Keyhani、Varoujan A. Yaylayan

  DOI：10.1021/jf950418u

  日期：1996.1.1

  Pyrolysis/GC/MS has been employed to analyze phenylalanine specific products formed during Maillard reaction. Phenylalanine Amadori product and different model systems containing phenylalanine and glucose, ribose, or glycerladehyde were studied. Ribbon pyrolysis was used to study the effect of temperature (150, 200, 250 degrees C) on the efficiency of formation of initial pyrolysis products from phenylalanine and Amadori phenylalanine. Quartz tube pyrolysis was used at 250 degrees C to enhance the secondary reactions. To address specific mechanistic questions, [1-C-13]glucose was used. These studies revealed the formation of pyridine and naphthalene derivatives such as 3,5-diphenylpyridine, 1(2)-naphthaleneamine, N-methyl-1(2)-aminonaphthalene, 1-aminoanthracene, 2'-phenylpyrrolo [4,5-a] dihydronaphthalene, 1(2)-(N-phenethyl)naphthaleneamine, and 1(2)-(N-phenethyl-N-methyl)naphthaleneamine. The precursors for pyridine and naphthalene derivatives were verified by GC/MS identification of the target compounds in the reaction mixtures of the postulated precursors.