N-(m-Chlorbenzyliden)-2-naphthylamin | 85378-37-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(m-Chlorbenzyliden)-2-naphthylamin
• 英文别名: N-[(3-Chlorophenyl)methylene]-2-naphthalenamine；1-(3-chlorophenyl)-N-naphthalen-2-ylmethanimine
• CAS: 85378-37-6
• 化学式: C₁₇H₁₂ClN
• 分子量: 265.742
• InChiKey: LGDUDLDHWHAVPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 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：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(m-Chlorbenzyliden)-2-naphthylamin 、 2-氧代环戊羧酸乙酯 在 盐酸 、 硝基苯 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以52%的产率得到6-(3-chlorophenyl)-2,3-dihydro-1H-benzo[f]cyclopenta[c]quinoline
  参考文献：
  名称：

  Kozlov; Popova; Yakubovich, Russian Journal of Organic Chemistry, 2000, vol. 36, # 11, p. 1667 - 1670

  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。
• 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。
• 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。