N-Naphthyl-N',N'-pentamethylen-hydrazin

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-Naphthyl-N',N'-pentamethylen-hydrazin
• 英文别名: N-naphthalen-1-ylpiperidin-1-amine
• 化学式: C₁₅H₁₈N₂
• 分子量: 226.321
• InChiKey: FSLBFOWYEREDQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  硝基萘 、 1-氨基哌啶 在 bis(acetylacetonato)palladium(II) 、 potassium phosphate monohydrate 、 2-(2,6-diethyl-4-methylphenyl)-5-(2,4,6-triisopropylphenyl)imidazo[1,5-a]pyridin-2-ium chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以86%的产率得到N-Naphthyl-N',N'-pentamethylen-hydrazin
  参考文献：
  名称：

  精心设计的N-杂环碳配体，用于钯催化硝基芳烃与胺的反硝化C-N偶联

  摘要：

  C–N键的形成是有机化学中的基本反应之一，因为药物和生物活性化合物中胺基的广泛存在。钯催化卤代芳烃的CN偶联是芳族胺最有效的方法之一。硝基芳烃价格低廉且易于获得，因此是理想的替代亲电偶联伙伴。使用硝基芳烃作为亲电子伴侣的脱硝和交叉偶联具有挑战性，因为Ar-NO 2键对氧化加成的反应性较低。我们在这里报告使用钯/ 5-（2,4,6-三异丙基苯基）咪唑基亚甲基[1,5- a以吡啶为催化剂。配体可容易地从商业化学品获得。该反应显示出广泛的底物范围和官能团耐受性。该方法适用于芳族和脂族胺，并且以高收率获得了带有各种官能团的许多仲和叔芳族胺。

  DOI：

  10.1021/acscatal.9b02760

文献信息

• 一种钯/咪唑盐催化硝基芳烃和胺类化合物合成芳香胺化合物的方法
  申请人：浙江大学

  公开号：CN110105230B

  公开（公告）日：2022-03-01

  本发明公开了一种钯/咪唑盐催化硝基芳烃和胺类化合物合成芳香胺的方法，包括：在有机溶剂中，以钯/咪唑盐为催化剂，将硝基芳烃和胺类化合物在碱的作用下进行偶联反应，经过后处理得到芳香胺化合物。本发明方法配体合成简单，易于保存，价格便宜且配体的用量较低，产物收率高，底物适用性好，可适用于二芳基胺、N‑烷基芳胺的制备。本发明方法可用于合成一系列芳香胺化合物，该类化合物在农药、医药、材料等领域均有广泛的应用价值。
• Palladium-CatalyzedN-Arylation ofN,N-Dialkylhydrazines with Aryl Chlorides
  作者：Sandro Cacchi、Giancarlo Fabrizi、Antonella Goggiamani、Simona Sgalla

  DOI：10.1002/adsc.200600299

  日期：2007.2.5

  N,N-Dialkyl-N′-arylhydrazines have been prepared usually in high to excellent yields via the reaction of N,N-dialkylhydrazines with aryl chlorides in the presence of Pd2(dba)3, Xphos and NaO-t-Bu in dioxane at 120 °C. With ortho-substituted aryl chlorides best results have been obtained by using 2-(2′,6′-dimethoxybiphenyl)dicyclohexylphosphine (ligand d) as the ligand.

  N，N- -二烷基N' -arylhydrazines已通常在高到经由反应优异的产率制备的N，N- -dialkylhydrazines与在Pd的存在下芳基氯化物2（DBA）3，XPHOS和NaO-叔卜在二恶烷在120°C下。与邻位取代的芳基氯化物已经通过使用获得的最佳结果2-（2'，6'-二甲氧基联苯）二环己基膦（配体d）作为配体。
• Aromatic heterocyclic compound, manufacturing method thereof, organic semiconductor material, and organic semiconductor device
  申请人：NIPPON STEEL & SUMIKIN CHEMICAL CO., LTD.

  公开号：US10032993B2

  公开（公告）日：2018-07-24

  Provided are an organic semiconductor material having a high charge mobility, oxidation stability, and solvent solubility, an organic semiconductor device using the same, and a novel aromatic heterocyclic compound to be used for the same and a production method therefor. The aromatic heterocyclic compound is represented by the following general formula (1), has two heteroatoms, and has a structure in which six rings are fused. In the formula, X represents an oxygen atom or N—R, and R represents hydrogen or a monovalent substituent. The organic semiconductor material contains the aromatic heterocyclic compound, and is used for an organic semiconductor film or an organic device, such as an organic thin-film transistor or an organic photovoltaic device.

  本文提供了一种具有高电荷迁移率、氧化稳定性和溶剂溶解性的有机半导体材料，一种使用该材料的有机半导体器件，以及一种可用于该材料的新型芳香杂环化合物及其生产方法。该芳香杂环化合物由以下通式（1）表示，具有两个杂原子，并具有六个环融合的结构。式中，X 代表氧原子或 N-R，R 代表氢或一价取代基。有机半导体材料含有芳香杂环化合物，可用于有机半导体薄膜或有机器件，如有机薄膜晶体管或有机光电器件。
• Synthesis of <i>N,N</i>-Dialkyl-<i>N</i><i>‘</i>-arylhydrazines via Palladium-Catalyzed N-Arylation by Using <i>N,N</i>-Dialkylhydrazines/2LiCl Adducts
  作者：Sandro Cacchi、Giancarlo Fabrizi、Antonella Goggiamani、Emanuela Licandro、Stefano Maiorana、Dario Perdicchia

  DOI：10.1021/ol050130i

  日期：2005.4.14

  [GRAPHICS]The reaction of N,N-dialkylhydrazine/2LiCl adducts with aryl bromides in the presence of Pd-2(dba)(3) as the palladium source, Xantphos or X-phos as the ligands, toluene as the solvent, and NaOBu-t as the base provides an efficient route to N,N-dialkyl-N,-arylhydrazines. Best results were obtained by using N,N-dialkylhydrazine/2LiCl adducts prepared in situ, omitting their isolation.
• AROMATIC HETEROCYCLIC COMPOUND, MANUFACTURING METHOD THEREOF, ORGANIC SEMICONDUCTOR MATERIAL, AND ORGANIC SEMICONDUCTOR DEVICE
  申请人：NIPPON STEEL & SUMIKIN CHEMICAL CO., LTD.

  公开号：US20160056390A1

  公开（公告）日：2016-02-25

  Provided are an organic semiconductor material having a high charge mobility, oxidation stability, and solvent solubility, an organic semiconductor device using the same, and a novel aromatic heterocyclic compound to be used for the same and a production method therefor. The aromatic heterocyclic compound is represented by the following general formula (1), has two heteroatoms, and has a structure in which six rings are fused. In the formula, X represents an oxygen atom or N—R, and R represents hydrogen or a monovalent substituent. The organic semiconductor material contains the aromatic heterocyclic compound, and is used for an organic semiconductor film or an organic device, such as an organic thin-film transistor or an organic photovoltaic device.