(3,4-dimethoxyphenyl)-methylene-2-naphthylamine | 68871-11-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (3,4-dimethoxyphenyl)-methylene-2-naphthylamine
• 英文别名: N-(3,4-dimethoxyphenylidene)naphthalen-2-amine；2-(3,4-dimethoxybenzylideneamino)naphthalene；N-(3,4-Dimethoxybenzyliden)-2-naphthylamin；N-(3,4-Dimethoxybenzylidene)naphthalen-2-amine；1-(3,4-dimethoxyphenyl)-N-naphthalen-2-ylmethanimine
• CAS: 68871-11-4
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: QWJJTXUZWKAGMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 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：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3,4-dimethoxyphenyl)-methylene-2-naphthylamine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 N-[(3,4-二甲氧基苯基)甲基]萘-2-胺
  参考文献：
  名称：

  Condensation of N-monosubstituted 2-naphthylamines, formaldehyde, and cyclic β-diketones. One-pot synthesis of 2,4-disubstituted derivatives of 1,2,3,4-tetrahydrobenzo[f]quinoline

  摘要：

  Various spirocyclic derivatives of 1,2,3,4-tetrahydrobenzo[f]quinoline containing substituents in the positions 2 and 4 of the ring were obtained by one-pot multicomponent condensation of available N-benzyl-2-naphthylamines, formaldehyde, and cyclic beta-diketones of cyclohexanedione series.

  DOI：

  10.1134/s1070428010090113
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 2-萘胺 以 乙醇 为溶剂， 反应 0.33h， 生成 (3,4-dimethoxyphenyl)-methylene-2-naphthylamine
  参考文献：
  名称：

  摘要：

  Condensation of N-arylmethylene-2-naphthylamines with ethyl 2-oxocycopentanecarboxylate in the presence of HCl or CH3COOH yields ethyl 2-hydroxy-3-[aryl(2-naphthylamino)methyl]-2-cyclopentene-carboxylates and ethyl 3-arylmethylene-2-(2-naphthylamino)-1-cyclopentenecarboxylates, respectively.

  DOI：

  10.1023/a:1015398523999

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。
• A clean synthesis of polyhydroacridine and indenoquinoline derivatives catalyzed by triethylbenzylammonium chloride 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：10.1002/jhet.5570430426

  日期：2006.7

  An efficient and convenient synthesis of benzo[a]acridines and indeno[1,2-b]benzo[f]quinolines was achieved in high yields by the reaction of N-arylidenenaphthalen-2-amine with 1,3-dicarbonyl compounds catalyzed with triethylbenzylammmonium chloride (TEBAC) in aqueous media. The structures were established by spectroscopic data and further confirmed by X-ray analysis. This method provides several advantages

  通过N-芳烯萘-2-胺与1,3-二羰基化合物的反应，可以高效合成苯并[ a ] r啶和茚并[1,2- b ]苯并[ f ]喹啉。三乙基苄基氯化铵（TEBAC）在水性介质中。通过光谱数据确定结构，并通过X射线分析进一步确认。该方法具有许多优点，例如中性条件，高收率和简单的后处理程序。另外，选择水作为绿色和可循环使用的溶剂。
• 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。
• 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。
• A simple and clean procedure for the synthesis of polyhydroacridine and quinoline derivatives: reaction of Schiff base with 1,3-dicarbonyl compounds in aqueous medium
  作者：Xiang-Shan Wang、Mei-Mei Zhang、Zhao-Sen Zeng、Da-Qing Shi、Shu-Jiang Tu、Xian-Yong Wei、Zhi-Min Zong

  DOI：10.1016/j.tetlet.2005.08.091

  日期：2005.10

  A clean and simple synthesis of benzo[c]acridine, benzo[a]acridine, pyrido[2,3-c]acridine and benzo[f]quinoline derivatives was accomplished in good to excellent yields via the reaction of Schiff base with 1,3-dicarbonyl compounds in aqueous medium catalyzed by TEBA. The structures were characterized by 1H NMR, IR and elemental analysis, and confirmed by X-ray diffraction study.

  通过席夫碱与1的反应，可以很好地收率很好地完成苯并[ c ] ac啶，苯并[ a ] ac啶，吡啶并[2,3- c ] ac啶和苯并[ f ]喹啉衍生物的清洁，简单合成。TEBA催化的水性介质中的3-二羰基化合物。通过1 H NMR，IR和元素分析对结构进行表征，并通过X射线衍射研究证实。