ethyl ((4-nitrophenyl)(2-hydroxynaphthalen-1-yl)methyl)carbamate | 1373618-70-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl ((4-nitrophenyl)(2-hydroxynaphthalen-1-yl)methyl)carbamate
• 英文别名: Ethyl [(4-nitrophenyl)(2-hydroxynaphthalen-1-yl)methyl]carbamate；ethyl N-[(2-hydroxynaphthalen-1-yl)-(4-nitrophenyl)methyl]carbamate
• CAS: 1373618-70-2
• 化学式: C₂₀H₁₈N₂O₅
• 分子量: 366.373
• InChiKey: XDDMGUDTVBYZFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  104
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对硝基苯甲醛 、 氨基甲酸乙酯 、 2-萘酚 在 a magnetite (Fe₃O₄ )supported -SO₃H functionalized benzimidazolium based ionic liquid 作用下， 以 neat (no solvent) 为溶剂， 反应 0.07h， 以95%的产率得到ethyl ((4-nitrophenyl)(2-hydroxynaphthalen-1-yl)methyl)carbamate
  参考文献：
  名称：

  Magnetically retrievable magnetite (Fe₃O₄) immobilized ionic liquid: an efficient catalyst for the preparation of 1-carbamatoalkyl-2-naphthols

  摘要：

  一种高效且更环保的协议，用于利用可磁性回收的离子液体合成1-氨基甲酸烷基-2-萘酚。

  DOI：

  10.1039/c5cy00849b

文献信息

• Solvent-free one-pot synthesis of 1-carbamatoalkyl-2-naphthols by a tin tetrachloride catalyzed multicomponent reaction
  作者：Min Wang、Qing L. Wang、Shuang Zhao、Xin Wan

  DOI：10.1007/s00706-013-0927-5

  日期：2013.7

  AbstractAn efficient one-pot synthesis of 1-carbamatoalkyl-2-naphthols using tin tetrachloride as a catalyst for the three-component condensation reaction of 2-naphthol, aldehydes, and carbamates under thermal, solvent-free conditions is described. This new approach has advantages such as mild conditions, short reaction time, high yield, simple work-up, and an inexpensive catalyst. Graphical Abstract

  摘要描述了使用四氯化锡作为催化剂在无溶剂热条件下有效合成2-萘酚，醛和氨基甲酸酯的三组分缩合反应的高效一锅法合成1-氨基甲酰基烷基-2-萘酚。这种新方法的优点包括条件温和，反应时间短，产率高，后处理简单和催化剂便宜。 图形概要
• Sulfamic acid Functionalised Magnetic Nanoparticles: An Efficient Solid Acid for the Multicomponent Condensations
  作者：Hossein Yarahmadi、Hamid Reza Shaterian

  DOI：10.3184/174751912x13264749420957

  日期：2012.1

  Sulfamic acid-functionalised magnetic nanoparticles have been synthesised and used as efficient heterogeneous solid acid catalysts for the condensation of aromatic aldehydes with 2-naphthol and amides (or carbamates) via three-component reactions under solvent-free conditions at 80°C. Quantitative conversion of the reactants is achieved under mild conditions. Recovery of the catalyst is easily achieved by ‘magnetic decantation’. The supported catalyst is reused four times without any significant degradation in catalytic activity.

  我们合成了氨基磺酸功能化磁性纳米粒子，并将其用作高效的异相固体酸催化剂，用于在 80°C 无溶剂条件下通过三组分反应使芳香醛与 2-萘酚和酰胺（或氨基甲酸酯）发生缩合反应。反应物可在温和条件下实现定量转化。通过 "磁性倾析 "可轻松回收催化剂。支撑催化剂可重复使用四次，催化活性不会明显降低。
• Graphene oxide supported dicationic ionic liquid: an efficient catalyst for the synthesis of 1-carbamatoalkyl-2-naphthols
  作者：Nipun Patel、Deepak Katheriya、Harsh Dadhania、Abhishek Dadhania

  DOI：10.1007/s11164-019-03922-0

  日期：2019.11

  DIL@GO was explored for the synthesis of 1-carbamatoalkyl-2-naphthol derivatives through condensation of aromatic aldehydes, alkyl carbamates and 2-naphthol. The influence of catalyst amount and reaction temperature is examined to optimize the performance of catalytic reactions. It is found that DIL@GO offers a highly efficient solvent-free reaction path for the synthesis of 1-carbamatoalkyl-2-naphthols

  本文介绍了氧化石墨烯（GO）负载的咪唑鎓型离子型离子液体（DIL @ GO）的合成，表征和催化应用。DIL @ GO是通过GO的逐步功能化成功合成的。所制备的DIL @ GO通过不同的显微和光谱技术进行表征，例如XRD，SEM，TEM，TGA，FT-IR，EDX和CHNS分析。通过芳香醛，烷基氨基甲酸酯和2-萘酚的缩合反应，研究了DIL @ GO催化1-氨基甲酰基烷基-2-萘酚衍生物的催化效率。检查催化剂量和反应温度的影响以优化催化反应的性能。发现DIL @ GO为合成1-氨基甲酰基烷基-2-萘酚提供了高效的无溶剂反应路径。基于此，提出了一种可行的转换机制。另外，该催化剂显示出良好的稳定性，容易的分离和至多五个反应循环的可重复使用性，而没有明显丧失催化活性。
• A convenient three-component synthesis of carbamatoalkyl naphthols catalyzed by cerium ammonium nitrate
  作者：M. Wang、Y. Liu、Z. Song、S. Zhao

  DOI：10.4314/bcse.v27i3.11

  日期：——

  A highly efficient synthesis of carbamatoalkyl naphthols has been performed by a one-pot three-component condensation of 2-naphthol, aldehydes, and methyl/ethyl/benzyl carbamates in the presence of cerium ammonium nitrate under solvent-free conditions at 70 oC. The solvent, optimal amounts of raw materials and catalyst, and reaction temperature are investigated. Experimental results show that only 0.1 mmol catalyst is enough to induce the conversion. Most reactions are performed within a short reaction time. The structures of all products were characterized by IR, 1H NMR, 13C NMR, MS, and elemental analysis. A mechanism to rationalize the reaction has been proposed.

  在无溶剂条件下，在70℃下，通过2-萘酚、醛类和甲基/乙基/苄基氨基甲酸酯在硝酸铈铵存在下的一锅三组分缩合，实现了氨基甲酸烷基萘酚的高效合成。对溶剂、最佳原料用量和催化剂以及反应温度进行了研究。实验结果表明，仅0.1mmol催化剂就足以引发转化。大多数反应在较短的反应时间内完成。通过红外光谱、1H核磁共振、13C核磁共振、质谱和元素分析对所有产物的结构进行了表征。提出了反应的合理化机制。
• Song, Zhiguo; Liu, Lianli; Sun, Xiaohu, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2014, vol. 53, # 6, p. 740 - 745
  作者：Song, Zhiguo、Liu, Lianli、Sun, Xiaohu、Cui, Yan

  DOI：——

  日期：——