ethyl ((4-chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl) carbamate | 1373618-60-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: ethyl ((4-chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl) carbamate
• 英文别名: Ethyl [(4-chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl]carbamate；ethyl N-[(4-chlorophenyl)-(2-hydroxynaphthalen-1-yl)methyl]carbamate
• CAS: 1373618-60-0
• 化学式: C₂₀H₁₈ClNO₃
• 分子量: 355.821
• InChiKey: ZAOAMIRWHHELRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 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：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 、 氨基甲酸乙酯 、 2-萘酚 在 sulfamic acid-functionalised magnetic nanoparticles 作用下， 反应 0.17h， 以82%的产率得到ethyl ((4-chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl) carbamate
  参考文献：
  名称：

  Sulfamic acid Functionalised Magnetic Nanoparticles: An Efficient Solid Acid for the Multicomponent Condensations

  摘要：

  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。

  DOI：

  10.3184/174751912x13264749420957

文献信息

• Solvent-free, highly efficient one-pot multi-component synthesis of 1-amido- and 1-carbamato-alkyl naphthols/phenols catalyzed by ethylammonium nitrate as reusable ionic liquid under neat reaction condition at ambient temperature
  作者：Shafeek A.R. Mulla、Tarek A. Salama、Mohsinkhan Y. Pathan、Suleman M. Inamdar、Santosh S. Chavan

  DOI：10.1016/j.tetlet.2012.12.004

  日期：2013.2

  developed for the efficient synthesis of 1-amido- and 1-carbamato-alkyl naphthols/phenols in excellent yields via one-pot three-component condensation of various aldehydes, amides/carbamates/urea, and naphthols/phenols using ethylammonium nitrate (EAN) as a reusable ionic liquid catalyst under neat reaction condition at ambient temperature.

  已开发出一种无溶剂，环境清洁，温和且简单的单锅多组分方案，可通过一锅三组分高效合成1-酰胺基和1-氨基甲酰基烷基萘酚/苯酚，且产率高在室温下纯净的反应条件下，使用硝酸乙铵（EAN）作为可重复使用的离子液体催化剂，将各种醛，酰胺/氨基甲酸酯/脲和萘酚/酚缩合。
• 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
• Magnetically retrievable magnetite (Fe₃O₄) immobilized ionic liquid: an efficient catalyst for the preparation of 1-carbamatoalkyl-2-naphthols
  作者：Harsh N. Dadhania、Dipak K. Raval、Abhishek N. Dadhania

  DOI：10.1039/c5cy00849b

  日期：——

  An efficient and greener protocol for the synthesis of 1-carbamatoalkyl-2-naphthols using magnetically retrievable ionic liquid.

  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。
• 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。
• Synthesis of 1-carbamatoalkyl-2-naphthols in Tween® 20 Aqueous Micelles
  作者：Jin-ming Yang、Chen-njing Jiang、Hao Dong、Dong Fang

  DOI：10.3184/174751913x13647554585207

  日期：2013.5

  A facile and efficient procedure for the preparation of 1-carbamatoalkyl-2-naphthols by a one-pot multi-component reaction of 2-naphthol, aldehydes and carbamates is described. The procedure is carried out under neutral conditions at 75–80 °C in an aqueous medium catalysed by the non-ionic surfactant Tween® A loading of 20. 5 wt% of the catalyst was optimal. After the reaction, the catalyst could be simply recovered and reused directly without any further treatment. Product yields were slightly decreased after six cycles. The effect of some common solvents other than water on the reaction was explored besides the water. The generality of this multi-component condensation reaction was evaluated with various aldehydes and carbamates under the optimised conditions.

  本文介绍了一种通过 2-萘酚、醛和氨基甲酸酯的单锅多组分反应制备 1-氨基甲酰基-2-萘酚的简便高效的方法。该反应在 75-80 °C 的中性条件下，在水介质中进行，非离子表面活性剂 Tween® A 的负载量为 20.5 wt% 的催化剂最为理想。反应结束后，催化剂可直接回收并重复使用，无需进一步处理。六次循环后，产品收率略有下降。除了水之外，还探讨了一些常见溶剂对反应的影响。在优化条件下，用各种醛类和氨基甲酸酯对这种多组分缩合反应的通用性进行了评估。