N-萘-2-基-1-(2-硝基苯基)甲亚胺 | 28303-90-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: N-萘-2-基-1-(2-硝基苯基)甲亚胺
• 英文名称: N-(2-nitrobenzylidene)-2-naphthylamine
• 英文别名: 2-Naphthalenamine, N-[(2-nitrophenyl)methylene]-；N-naphthalen-2-yl-1-(2-nitrophenyl)methanimine
• CAS: 28303-90-4
• 化学式: C₁₇H₁₂N₂O₂
• 分子量: 276.294
• InChiKey: BMWZQZVBKDJICA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-萘-2-基-1-(2-硝基苯基)甲亚胺 在 频哪醇 、 {MoO2Cl2(dmf)2} 作用下， 以 neat (no solvent) 为溶剂， 反应 10.0h， 以90%的产率得到2-(naphth-2-yl)-2H-indazole
  参考文献：
  名称：

  Mo(VI)-catalyzed Synthesis of 2-Aryl-2H-indazoles Using Pinacol Mediated Deoxygenation of Nitroaromatics

  摘要：

  在纯净反应条件下，以频哪醇为还原剂，展示了一种钼（VI）催化的 2-芳基-2H-吲唑合成方案。所开发的方法能以极佳的产率轻松获得多种 2-芳基-2H-吲唑。本方法无需使用 P(III) 试剂作为脱氧剂。

  DOI：

  10.1246/cl.190490
• 作为产物：
  描述：

  2-萘胺 、 邻硝基苯甲醛 以 乙醇 为溶剂， 反应 24.0h， 生成 N-萘-2-基-1-(2-硝基苯基)甲亚胺
  参考文献：
  名称：

  Martinez, Roberto; Cortes, Eduardo; Toscano, Ruben A., Journal of Heterocyclic Chemistry, 1990, vol. 27, # 5, p. 1273 - 1276

  摘要：

  DOI：

文献信息

• A new synthesis method for benzo[<i>f</i>]quinolin-3-carbonyl urea and thiourea derivatives in aqueous media catalyzed by TEBAC
  作者：Xiang-Shan Wang、Mei-Mei Zhang、Zhao-Sen Zeng、Da-Qing Shi、Shu-Jiang Tu、Xian-Yong Wei、Zhi-Min Zong

  DOI：10.1002/jhet.5570440226

  日期：2007.3

  A clean and simple synthesis procedure for benzo[f]quinolin-3-carbonyl urea and thiourea derivatives was developed based on the reaction between N-arylidenenaphthalen-2-amine and barbituric acid or thiobarbituric acid in aqueous media catalyzed by triethylbenzylammonium chloride (TEBAC). It was interesting that the structures of products in solvent of DMSO-d6 solution were different from those of the

  基于三乙基苄基氯化铵（TEBAC）在水介质中N-芳基萘-2-胺与巴比妥酸或硫代巴比妥酸之间的反应，开发了一种清洁，简单的苯并[ f ]喹啉-3-羰基脲和硫脲衍生物的合成方法。有趣的是，在DMSO- d 6溶液的溶剂中产物的结构与保持烯醇形式的晶态不同。产物通过1 H NMR和13 C NMR进行表征，并且通过3e的X射线衍射研究确认了晶体状态。另外，选择水作为绿色溶剂。
• An Unexpected Triethylbenzylammonium Chloride Catalyzed Ring Opening of 2-Pyrones in the Synthesis of 1-Arylbenzo[<i>f</i>]quinoline-2-carboxamide Derivatives in Aqueous Media
  作者：Xiang-Shan Wang、Mei-Mei Zhang、Qing Li、Chang-Sheng Yao、Shu-Jiang Tu

  DOI：10.1055/s-2007-990897

  日期：——

  Reaction of N-arylidenenaphthalen-2-amine and 4-hydroxy-6-methylpyran-2-one in aqueous media catalyzed by triethylbenzylammonium chloride (TEBAC) at 90 °C unexpectedly gave a pyrone ring-opening product 1-aryl-1,4-dihydro-3-[(E)-2-hydroxy­prop-1-enyl]-N-(naphthalene-2-yl)benzo[f]quinoline-2-carbox­amide. Modification of the reaction protocol resulted in a three-component reaction among N-arylidenenaphthalen-2-amine, 4-hydroxy-6-methylpyran-2-one and naphthalen-2-amine.

  N-芳基亚胺-2-萘胺与4-羟基-6-梅基吡喃-2-酮在水相介质中，通过三乙基苄胺氯化物（TEBAC）催化，在90°C下反应，意外产生了一种吡酮环开环产物1-芳基-1,4-二氢-3-[(E)-2-羟基丙-1-烯基]-N-(萘-2-基)苯并[f]喹啉-2-羧酰胺。反应方案的修改导致了N-芳基亚胺-2-萘胺、4-羟基-6-梅基吡喃-2-酮和萘-2-胺之间的三组分反应。
• Unexpected Spiro-benzoquinolines in the Reaction of<i>N</i>-(Arylidene)naphthalen-2-amine, Arylaldehyde, and 1,3-Dimethylbarbituric Acid in Water
  作者：Xiang-Shan Wang、Mei-Mei Zhang、Hong Jiang、Chang-Sheng Yao、Shu-Jiang Tu

  DOI：10.1246/cl.2007.450

  日期：2007.3.5

  A series of unexpected pyrimidine spiro-benzoquinolines were developed based on the reaction of N-(arylidene)naphthalen-2-amine, arylaldehyde, 1,3-dimethylbarbituric acid in aqueous media catalyzed by triethylbenzylammonium chloride (TEBAC). The structure of the product 4a was confirmed by X-ray diffraction studies. In addition, the water was chosen as green solvent.

  一系列意想不到的吡啶并苯醌类化合物是在水相中，通过三乙基苄基铵氯化物（TEBAC）催化N-(芳基亚胺)萘-2-胺、芳醛和1,3-二甲基巴比妥酸的反应开发的。产物4a的结构通过X射线衍射研究得到了证实。此外，水被选择作为绿色溶剂。
• A Clean Procedure for the Synthesis of Chromeno[4,3-<i>b</i>]benzo[<i>f</i>]quinoline and Quinolino[4,3-<i>b</i>]benzo[<i>f</i>]quinoline Derivatives in Aqueous Media
  作者：Xiang-Shan Wang、Mei-Mei Zhang、Zhao-Sen Zeng、Da-Qing Shi、Shu-Jiang Tu、Xian-Yong Wei、Zhi-Min Zong

  DOI：10.1246/cl.2005.1316

  日期：2005.10

  A short and simple synthesis of chromeno[4,3-b]benzo[f]-quinoline and quinolino[4,3-b]benzo[f]quinoline derivatives were accomplished in high yields via the reaction of N-benzilidenenaphthalen-2-amine and 4-hydroxycoumarin or 4-hydroxyquinolin-2-one in aqueous media catalyzed by TEBAC. The structures were established by spectroscopic data and further confirmed by X-ray diffraction analysis.

  通过 N-benzilidenenaphthalen-2- 的反应，以高产率完成了 chromeno[4,3-b]benzo[f]-quinoline 和 quinolino[4,3-b]benzo[f]quinoline 衍生物的简短而简单的合成胺和 4-羟基香豆素或 4-羟基喹啉-2-one 在由 TEBAC 催化的水性介质中。这些结构是通过光谱数据建立的，并通过 X 射线衍射分析进一步证实。
• Clean Procedure for Synthesis of Chromeno[4,3‐<i>b</i>]benzo [<i>f</i>]quinolin‐6‐one Derivatives: Reaction of<i>N</i>‐arylidenenaphthalen‐2‐amine with 4‐Hydroxycoumarin in Aqueous Media
  作者：Xiang‐Shan Wang、Mei‐Mei Zhang、Zhao‐Sen Zeng、Da‐Qing Shi、Shu‐Jiang Tu

  DOI：10.1080/00397910600634449

  日期：2006.6

  Abstract A short and simple synthesis of chromeno[4,3‐b]benzo[f]quinolin‐6‐one derivatives was accomplished in good to high yields via the reaction of N‐arylidenenaphthalen‐2‐amine with 4‐hydroxycoumarin in aqueous media catalyzed by TEBAC. The structures were established by spectroscopic data and further confirmed by X‐ray analysis. In addition, water was chosen as a green solvent.

  摘要 通过 N-亚芳基萘-2-胺与 4-羟基香豆素在水性介质中的反应，以良好至高收率完成了色基[4,3-b]苯并[f]喹啉-6-酮衍生物的简短合成。由TEBAC催化。这些结构是通过光谱数据建立的，并通过 X 射线分析进一步证实。此外，选择水作为绿色溶剂。