methyl ((2-chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl)carbamate

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: methyl ((2-chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl)carbamate
• 英文别名: Methyl [(2-chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl]carbamate；methyl N-[(2-chlorophenyl)-(2-hydroxynaphthalen-1-yl)methyl]carbamate
• 化学式: C₁₉H₁₆ClNO₃
• 分子量: 341.794
• InChiKey: BQDQNFFMAZQRRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 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：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl ((2-chlorophenyl)(2-hydroxynaphthalen-1-yl)methyl)carbamate 在 1-丁基-3-甲基咪唑溴盐 作用下， 反应 0.5h， 以73%的产率得到1-(2-chlorophenyl)-1,2-dihydronaphtho[1,2-e][1,3]oxazin-3-one
  参考文献：
  名称：

  Dabiri, Minoo; Delbari, Akram Sadat; Bazgir, Ayoob, Heterocycles, 2007, vol. 71, # 3, p. 543 - 548

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯苯甲醛 、 氨基甲酸甲酯 、 2-萘酚 在 sulfamic acid-functionalised magnetic nanoparticles 作用下， 反应 0.2h， 以82%的产率得到methyl ((2-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

• Evaluation of catalytic activity of two newly prepared functionalized sulfonic acids ionic liquids in the synthesis of carbamatoalkyl naphthols under mild conditions
  作者：M. Dehghan、A. Davoodnia、M. R. Bozorgmehr、F. F. Bamoharram

  DOI：10.1134/s1070363217020268

  日期：2017.2

  activity of two newly prepared functionalized sulfonic acids ionic liquids, [MPyrrSO3H]Cl (IL1) and [MMorSO3H]Cl (IL2), is studied in one-pot three-component synthesis of carbamatoalkyl naphthols by the reaction of β-naphthol with aromatic aldehydes and methyl or benzyl carbamate. The efficiently catalyzed reaction proceeded under solvent-free conditions. The synthesis was characterized by easy work-up

  在单锅三组分合成氨基甲酰基烷基萘酚的反应中，研究了两种新制备的官能化磺酸离子液体[MPyrrSO 3 H] Cl（IL 1）和[MMorSO 3 H] Cl（IL 2）的催化活性。β-萘酚与芳族醛和氨基甲酸甲酯或氨基甲酸苄酯的合成 在无溶剂条件下进行有效催化的反应。合成的特征在于易于后处理，不存在挥发性和有害的有机溶剂以及催化剂的可回收性。
• 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
• Preparation of methyl/benzyl(2-hydroxynaphthalen-1-yl)(aryl)methylcarbamate derivatives using magnesium hydrogen sulfate
  作者：Majid Ghashang

  DOI：10.1007/s11164-013-1044-0

  日期：2014.4

  A new approach to the synthesis of methyl/benzyl(2-hydroxynaphthalen-1-yl)(aryl)methylcarbamate derivatives based on the reaction of aldehydes, 2-naphthol and methyl/benzyl carbamate, using a catalytic amount of magnesium hydrogen sulfate [Mg(HSO4)2] as an efficient heterogeneous catalyst under solvent-free conditions has been developed.

  本研究以醛、2-萘酚和氨基甲酸甲酯/苄酯反应为基础，开发了一种在无溶剂条件下使用催化量硫酸氢镁 [Mg(HSO4)2] 作为高效异相催化剂合成(2-羟基萘-1-基)(芳基)甲基氨基甲酸甲酯/苄酯衍生物的新方法。
• 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。
• Preparation of Methyl (2-hydroxynaphthalen-1-yl)(aryl)methyl/benzylcarbamate derivatives using magnesium (II) 2,2,2-trifluoroacetate as an efficient catalyst
  作者：Mohammad Reza Mohammad Shafiee、Raheleh Moloudi、Majid Ghashang

  DOI：10.3184/174751911x13182405888457

  日期：2011.11

  2-naphthol and methyl/benzyl carbamate have been done by using magnesium 2,2,2-trifluoroacetate [Mg(OOCCF3)2] as an efficient catalyst. This methodology results in the synthesis of a variety of methyl (2-hydroxynaphthalen-1-yl)(aryl)methyl/benzylcarbamate derivatives in high yields. Despite their importance from pharmacological and synthetic points of view, comparatively few methods for the preparation of 1-carbamatoalkyl

  醛、2-萘酚和甲基/苄基氨基甲酸酯的多组分缩合反应已通过使用 2,2,2-三氟乙酸镁 [Mg(OOCCF3)2] 作为有效催化剂进行。这种方法导致以高产率合成各种甲基（2-羟基萘-1-基）（芳基）甲基/苄基氨基甲酸酯衍生物。尽管从药理学和合成的角度来看它们很重要，但通过醛、2-萘酚和氨基甲酸酯的多组分反应使用酸性催化剂制备 1-氨基甲酸烷基 2-萘酚衍生物的方法相对较少。2,2,2-三氟乙酸镁[Mg(OOCCF3)2]由三氟乙酸和氯化镁反应制备。制备的催化剂已通过粉末 X 射线衍射图表征。