N,N-二苄基-3-氟苯胺 | 103818-28-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N,N-二苄基-3-氟苯胺
• 英文名称: N,N-dibenzyl-3-fluoroaniline
• CAS: 103818-28-6
• 化学式: C₂₀H₁₈FN
• 分子量: 291.368
• InChiKey: RGMIPYMGDXLDFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-二苄基-3-氟苯胺 在 盐酸 、 硫酸 、 溶剂黄146 、 三氯氧磷 作用下， 以 乙醚 为溶剂， 反应 44.0h， 生成 [4-(2-Amino-2-methyl-propyl)-3-fluoro-phenyl]-dibenzyl-amine
  参考文献：
  名称：

  Selective monoamine oxidase inhibitors. 4. 4-Aminophenethylamine derivatives with neuron-selective action

  摘要：

  Nine 4-aminophenethylamine derivatives were synthesized and tested for monoamine oxidase (MAO) inhibitory effects with particular attention to their selectivity for MAO within monoaminergic neurons in the rat brain. All compounds selectively inhibited the A form of MAO in vitro. Some of the compounds inhibited the MAO within the monoaminergic neurons at much lower doses than those required for inhibition of MAO within other cells in vivo. The most potent compounds in this respect were 4-amino-2-fluoro-alpha-methylphenethylamine (5) and 4-amino-2-chloro-alpha-methylphenethylamine (4).

  DOI：

  10.1021/jm00161a020
• 作为产物：
  描述：

  3-氟苯胺 、 氯化苄 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以76%的产率得到N,N-二苄基-3-氟苯胺
  参考文献：
  名称：

  Selective monoamine oxidase inhibitors. 4. 4-Aminophenethylamine derivatives with neuron-selective action

  摘要：

  Nine 4-aminophenethylamine derivatives were synthesized and tested for monoamine oxidase (MAO) inhibitory effects with particular attention to their selectivity for MAO within monoaminergic neurons in the rat brain. All compounds selectively inhibited the A form of MAO in vitro. Some of the compounds inhibited the MAO within the monoaminergic neurons at much lower doses than those required for inhibition of MAO within other cells in vivo. The most potent compounds in this respect were 4-amino-2-fluoro-alpha-methylphenethylamine (5) and 4-amino-2-chloro-alpha-methylphenethylamine (4).

  DOI：

  10.1021/jm00161a020

文献信息

• Selective Para‐C−H Alkynylation of Aniline Derivatives by Pd/S,O‐Ligand Catalysis
  作者：Ke‐Zuan Deng、Wen‐Liang Jia、M. Ángeles Fernández‐Ibáñez

  DOI：10.1002/chem.202104107

  日期：2022.2.16

  para-Alkynylated aromatic amines are obtained without the need to prefunctionalize the starting aniline by Pd/S,O-ligand catalyzed C−H alkynylation reactions.

  通过 Pd/S,O-配体催化的 C−H 炔基化反应无需对起始苯胺进行预官能化即可获得对炔基化芳香胺。
• <i>meta</i>‐C−H Arylation of Aniline Derivatives via Palladium/ S,O‐Ligand/Norbornene Cooperative Catalysis
  作者：Verena Sukowski、Manuela van Borselen、Simon Mathew、Bas de Bruin、M. Ángeles Fernández‐Ibáñez

  DOI：10.1002/anie.202317741

  日期：2024.1.25

  Aromatic amines are ubiquitous moieties in organic molecules and their direct functionalization is of great interest in many research areas due to their prevalence in pharmaceuticals and organic electronics. While several synthetic tools exist for the ortho‐ and para‐functionalization of anilines, the functionalization of the less reactive meta‐position is not easy to achieve with current methods. To date, the meta‐C−H arylation of aniline derivatives has been restricted to either the use of directing groups & templates, or their transformation into anilides & quaternary anilinium salts. Herein, we report the first general and efficient meta‐C−H‐arylation of non‐directed aniline derivatives via cooperative catalysis with a palladium–S,O‐ligand–norbornene system. The reaction proceeds under mild conditions with a wide range of aniline derivatives and aryl iodides, while being operationally simple and scalable. Our preliminary mechanistic investigation–including the isolation of several palladium complexes and deuterium experiments–reveal useful insights into the substituent‐effects of both the aniline‐substrate and the norbornene‐mediator during the meta‐C−H activation step.

  摘要 芳香胺是有机分子中无处不在的分子，由于芳香胺在医药和有机电子产品中的广泛应用，其直接官能化在许多研究领域都引起了极大的兴趣。虽然有多种合成工具可以实现苯胺的正官能化和对官能化，但目前的方法却难以实现反应性较低的元位的官能化。迄今为止，苯胺衍生物的元-C-H 芳基化仅限于使用定向基团和模板，或将其转化为苯胺类和季胺盐。在此，我们首次报道了通过钯-S,O-配体-降冰片烯体系的协同催化，对非定向苯胺衍生物进行通用而高效的元-C-H-芳基化反应。该反应在温和的条件下进行，适用于多种苯胺衍生物和芳基碘化物，同时操作简单、规模可控。我们的初步机理研究--包括分离几种钯配合物和氘实验--揭示了在元-C-H 活化步骤中苯胺底物和降冰片烯介质的取代效应。
• Photoconductive devices containing novel squaraine compounds
  申请人：XEROX CORPORATION

  公开号：EP0145400A2

  公开（公告）日：1985-06-19

  This invention is generally directed to fluorinated squaraine compositions of the formula: wherein R,. R2, R3, and R4, are independently selected from alkyl groups, containing from about 1 to about 20 carbon atoms, and layered photoresponsive devices containing such compositions.

  本发明一般涉及式中的氟化方碱组合物： 其中RR2、R3 和 R4 分别独立地选自含有约 1 至约 20 个碳原子的烷基，以及含有此类组合物的层状光致发光器件。
• FLORVALL L.; FAGERVALL I.; ASK A. -L.; ROSS S. B., J. MED. CHEM., 29,(1986) N 11, 2250-2256
  作者：FLORVALL L.、 FAGERVALL I.、 ASK A. -L.、 ROSS S. B.

  DOI：——

  日期：——
• Process for synthesising squaraine compositions
  申请人：XEROX CORPORATION

  公开号：EP0144206B1

  公开（公告）日：1989-04-19