1-((4-bromophenyl)(piperidin-1-yl)methyl)naphthalen-2-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-((4-bromophenyl)(piperidin-1-yl)methyl)naphthalen-2-ol
• 英文别名: 1-(alpha-Piperidino-4-bromobenzyl)-2-naphthol；1-[(4-bromophenyl)-piperidin-1-ylmethyl]naphthalen-2-ol
• 化学式: C₂₂H₂₂BrNO
• 分子量: 396.327
• InChiKey: BOFXEAJNXZDDLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  哌啶 、 对溴苯甲醛 、 2-萘酚 在 Amberlite IRA-400 Cl resin 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以91%的产率得到1-((4-bromophenyl)(piperidin-1-yl)methyl)naphthalen-2-ol
  参考文献：
  名称：

  氨基烷基萘酚的简便合成和单晶 X 射线，1-[morpholino(thiophen-2-yl)methyl]naphthalen-2-ol 的计算研究

  摘要：

  开发了一种高效、环保的协议，用于在 Amberlite IRA 存在下，通过 2-萘酚、芳香醛和哌啶或吗啉的一锅三组分反应合成 1-（α-氨基烷基）-2-萘酚衍生物-400 Cl树脂作催化剂。该方法具有一锅法合成、收率高、反应条件温和、清洁的特点，催化剂可回收利用。得到其中一种产物（4p），在具有 P32 空间群的三角晶系中结晶，并与流行的密度泛函理论（DFT）、B3LYP/6-311++G(d,p) 基组的理论计算进行比较. 计算了最高占据分子轨道（HOMO）和最低未占据分子轨道（LUMO）的能量。所有理论计算与实验值一致。

  DOI：

  10.1016/j.molstruc.2021.130861

文献信息

• Aluminatesulfonic acid: Novel and recyclable nanocatalyst for efficient synthesis of aminoalkyl naphthols and amidoalkyl naphthols
  作者：Masoud Nasr-Esfahani、Morteza Montazerozohori、Mahbube Taei

  DOI：10.1016/j.crci.2016.02.003

  日期：2016.8

  Résumé In this study, an efficient, mild, and eco-friendly procedure is developed for the preparation of 1-amidoalkyl-2-naphthols and Betti bases from one-pot three-component condensation of aldehydes, 2-naphthol, and nitrogen sources (amides for amidoalkyl naphthols and amine for Betti bases) in the presence of aluminatesulfonic acid nanoparticles (ASA NPs) as recoverable catalyst under solvent-free conditions. ASA NPs were prepared by a simple reaction of net chlorosulfonic acid and sodium aluminate in high purity. ASA NPs were characterized by Fourier transform IR, X-ray powder diffraction, transmission electron microscopy, energy-dispersive X-ray, thermal gravimetric analysis, and UV diffusion/reflectance techniques. On the basis of the thermal gravimetric analysis and some activation parameters evaluated from decomposition thermal steps using Coats–Redfern model, the catalyst showed high thermal stability. High yields, short reaction time, easy workup, inexpensive, and reusability of the catalyst are advantages of this method.

  摘要 在本研究中，开发了一种高效、温和且环保的程序，用于通过醛、2-萘酚和氮源（用于酰胺烷基萘酚的酰胺和用于Betti碱的胺）的一锅三组分缩合制备1-酰胺烷基-2-萘酚和Betti碱，反应在无溶剂条件下进行，使用铝酸盐磺酸纳米颗粒（ASA NPs）作为可回收催化剂。ASA NPs通过净氯磺酸与高纯度铝酸钠的简单反应制备。 ASA NPs通过傅里叶变换红外光谱、X射线粉末衍射、透射电子显微镜、能量色散X射线、热重分析和UV扩散/反射技术进行了表征。根据热重分析和使用Coats-Redfern模型评估的分解热步骤的一些活化参数，催化剂显示出高热稳定性。该方法的优点包括高产率、短反应时间、容易的后处理、成本低廉以及催化剂的可重用性。
• Multicomponent reaction in deep eutectic solvent for synthesis of substituted 1-aminoalkyl-2-naphthols
  作者：Najmedin Azizi、Mahtab Edrisi

  DOI：10.1007/s11164-016-2628-2

  日期：2017.1

  One-pot multicomponent synthesis of Betti bases (aminoalkyl naphthols) from aldehydes, β-naphthol, and secondary amines in deep eutectic solvent (DES) based on urea and choline chloride has been developed. A broad range of aminoalkyl naphthols can be obtained smoothly in good to excellent yield in biodegradable choline-chloride-based deep eutectic solvent, being compatible with functional groups and

  已经开发了在尿素和氯化胆碱的基础上，由乙醛，β-萘酚和仲胺在深共熔溶剂（DES）中一锅多组分合成Betti碱（氨基烷基萘）的方法。在可生物降解的基于胆碱-氯化物的深共熔溶剂中，与官能团兼容且操作简便，可以顺利获得各种各样的氨基烷基萘，并以良好或优异的收率获得。另外，DES可以很容易地循环至少四次而不会明显丧失活性。
• Supported copper triflate as an efficient catalytic system for the synthesis of highly functionalized 2-naphthol Mannich bases under solvent free condition
  作者：Someshwar D. Dindulkar、Vedavati G. Puranik、Yeon Tae Jeong

  DOI：10.1016/j.tetlet.2012.06.022

  日期：2012.8

  Various heterogeneous catalysts (Lewis acid) have been prepared and screened for the synthesis of Betti bases in an attempt to reduce the environmental hazards associated with the conventional homogeneous Lewis acid system. And we found especially Cu(OTf)(2)center dot SiO2 catalyzes the three-component coupling of aldehyde, 2-naphthol, and alicyclic amine to generate Betti base with high efficiency under neat conditions without additional co-catalyst or additive in air. The reaction is not sensitive to water and occurs smoothly in water as well. (c) 2012 Elsevier Ltd. All rights reserved.
• Core–shell structured magnetic mesoporous silica-titania: A novel, powerful and recoverable nanocatalyst
  作者：Marziyeh Vahidian、Dawood Elhamifar、Masoumeh Shaker

  DOI：10.1016/j.poly.2019.114326

  日期：2020.3

  In this research, a novel core-shell nanostructured magnetic Ti-silica (Mag@MCM-41/TiO2) is synthesized, characterized and its catalytic application is investigated in the production of 1-(alpha-aminoalkyl)-2-naphthols. The Mag@MCM-41/TiO2 was prepared via surfactant directed hydrolysis and co-condensation of tetramethoxysilane (TMOS) around Mag@SiO2 NPs followed by treatment with tetrabutylorthotitanate (Ti((OBu)-Bu-t)(4)). The Mag@MCM-41/TiO2 catalyst was characterized using VSM, FTIR, EDX, SEM, TEM and PXRD. The Mag@MCM-41/TiO2 was applied as an efficient catalyst in the synthesis of 1-(alpha-aminoalkyl)-2-naphthols under ultrasonic conditions at 50 degrees C. This nanocatalyst was recovered and reused for several times under applied conditions. (C) 2019 Elsevier Ltd. All rights reserved.
• Catalyst-Free, One-Pot, Expeditious Synthesis of Aminoalkylnaphthols at Room Temperature
  作者：Chhanda Mukhopadhyay、Sunil Rana、Ray J. Butcher

  DOI：10.1080/00397911.2011.575524

  日期：2012.10.15

  Aminoalkylnaphthols possess several biological and catalytic activities. A methodology has been developed for the multicomponent one-pot synthesis of aminoalkylnaphthols in dichloromethane under catalyst-free conditions at room temperature. The present approach possesses several advantages such as excellent yields, quick reaction time, mild reaction conditions, and very easy purification processes. Thirteen new compounds in addition to six known compounds have been synthesized by this methodology.