1-(2-methoxyphenyl(pyrrolidine-1-yl)methyl)naphthalen-2-ol | 1219978-23-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(2-methoxyphenyl(pyrrolidine-1-yl)methyl)naphthalen-2-ol
• 英文别名: 1-((2-methoxyphenyl)(pyrrolidin-1-yl)methyl)naphthalen-2-ol；1-[(2-Methoxyphenyl)-pyrrolidin-1-ylmethyl]naphthalen-2-ol；1-[(2-methoxyphenyl)-pyrrolidin-1-ylmethyl]naphthalen-2-ol
• CAS: 1219978-23-0
• 化学式: C₂₂H₂₃NO₂
• 分子量: 333.43
• InChiKey: OMWGEINKKNWPSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  四氢吡咯 、 邻甲氧基苯甲醛 、 2-萘酚 在 Montmorillonite K₃₀ 作用下， 以 neat (no solvent) 为溶剂， 反应 6.0h， 以60%的产率得到1-(2-methoxyphenyl(pyrrolidine-1-yl)methyl)naphthalen-2-ol
  参考文献：
  名称：

  回顾Betti合成：在无溶剂条件下使用廉价，易得的可回收粘土催化剂

  摘要：

  一锅多组分Betti合成是在绿色多相和纯净条件下，在蒙脱土K30催化剂存在下进行的，该方法安全，便宜且可商购，不需要任何制备。它是完全可回收和可回收的，最多可运行5次。仲和伯脂族胺均以良好至优异的产率提供产物。开发的协议显示出很高的Atom经济性和低E因子。

  DOI：

  10.1002/ejoc.201800826

文献信息

• Nanocrystalline TiO2–HClO4 catalyzed three-component preparation of derivatives of 1-amidoalkyl-2-naphthol, 1-carbamato-alkyl-2-naphthol, 1-(α-aminoalkyl)-2-naphthol, and 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-one
  作者：Hamid Reza Shaterian、Majid Mohammadnia

  DOI：10.1007/s11164-012-0938-6

  日期：2013.11

  1-Amidoalkyl-2-naphthols, 1-carbamatoalkyl-2-naphthols, and 1-(α-aminoalkyl)-2-naphthols have been prepared by three-component reaction of 2-naphthol, aromatic aldehydes, and NH compounds, i.e. amides, carbamates, and secondary amines, respectively, in the presence of a catalytic amount of nanocrystalline TiO2–HClO4. In addition, 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-one derivatives have been synthesized by reaction of 2-naphthol, aromatic aldehydes, and dimedone in the presence of the same nano catalyst. These reactions were studied under solvent-free conditions. This white acidic heterogeneous catalyst is very stable under the reaction conditions and was reused several times without significant loss of activity.

  在催化剂纳米晶 TiO2-HClO4 的存在下，通过 2-萘酚、芳香醛和 NH 化合物（即酰胺、氨基甲酸酯和仲胺）的三组分反应，分别制备了 1-氨基烷基-2-萘酚、1-氨基甲酰基-2-萘酚和 1-(α-氨基烷基)-2-萘酚。此外，在相同的纳米催化剂存在下，通过 2-萘酚、芳香醛和二甲酮的反应，合成了 12-芳基-8,9,10,12-四氢苯并[a]-氧杂蒽-11-酮衍生物。这些反应是在无溶剂条件下进行研究的。这种白色酸性异相催化剂在反应条件下非常稳定，可重复使用多次，且活性无明显下降。
• Solventless Synthesis of 1-(α-aminoalkyl) Naphthols, Betti Bases, Catalyzed by Nanoparticle Fe₃O₄ at Room Temperature
  作者：Fatemeh Janati、Majid M. Heravi、Ahmad Mir Shokraie

  DOI：10.1080/15533174.2012.762381

  日期：2015.1.2

  A series of 1-(alpha-aminoalkyl) naphthols were synthesized expeditiously in good yields and selectivity from 2-naphthol, alkylamines and aldehydes in the presence of nanoparticle Fe3O4 at room temperature in solvent-free conditions.
• Non-ionic surfactant catalyzed synthesis of Betti base in water
  作者：Atul Kumar、Maneesh Kumar Gupta、Mukesh Kumar

  DOI：10.1016/j.tetlet.2010.01.056

  日期：2010.3

  We have developed an efficient non-ionic surfactant (Triton X-100) catalyzed multicomponent synthesis of Betti base from secondary amine, aromatic aldehydes, and beta-naphthol using Mannich-type reaction in water. Lewis and Bronsted acid catalysts, ionic and non-ionic surfactant have been screened for the reaction. Non-ionic surfactant (Triton X-100) gave the best results and the reaction proceeds through the imine formation, which is stabilized by colloidal dispersion and undergoes nucleophilic addition to afford the corresponding N,N-dialkylated Betti base in excellent yields. (C) 2010 Elsevier Ltd. All rights reserved.