1-(4-cyanophenyl(piperidine-1-yl)methyl)naphthalen-2-ol | 1208099-40-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(4-cyanophenyl(piperidine-1-yl)methyl)naphthalen-2-ol
• 英文别名: 1-((4-cyanophenyl)(piperidin-1-yl)methyl)naphthalen-2-ol；4-[(2-Hydroxynaphthalen-1-yl)-piperidin-1-ylmethyl]benzonitrile；4-[(2-hydroxynaphthalen-1-yl)-piperidin-1-ylmethyl]benzonitrile
• CAS: 1208099-40-4
• 化学式: C₂₃H₂₂N₂O
• 分子量: 342.44
• InChiKey: RDQSSGODUHBVBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  47.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  哌啶 、 4-氰基苯甲醛 、 2-萘酚 在 Amberlite IRA-400 Cl resin 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以92%的产率得到1-(4-cyanophenyl(piperidine-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

• Revisiting the Betti Synthesis: Using a Cheap, Readily Available, Recyclable Clay Catalyst under Solventless Conditions
  作者：Giovanna Bosica、Roderick Abdilla、Kaylie Demanuele

  DOI：10.1002/ejoc.201800826

  日期：2018.12.2

  and neat conditions in the presence of Montmorillonite K30 catalyst, which is safe, cheap, and commercially available and does not require any preparations. It is fully recoverable and recyclable for up to 5 runs. Both secondary and primary aliphatic amines give products in good to excellent yields. The developed protocol displays a very high Atom Economy and a low E‐Factor.

  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。
• Gold nanoparticles deposited on MnO2 nanorods modified graphene oxide composite: A potential ternary nanocatalyst for efficient synthesis of betti bases and bisamides
  作者：Pratap S. Nayak、Bapun Barik、L. Satish K. Achary、Aniket Kumar、Priyabrat Dash

  DOI：10.1016/j.mcat.2019.110415

  日期：2019.9

  The decoration of novel nanostructures such as nano particle and nanorod on the surface of graphene oxide (GO) generate potential heterogeneous nanocatalyst. Highlighting this, in the present work, we have designed a ternary GO-MnO2-Au nanocomposite by decorating MnO(2)nanorods on the surface of graphene oxide via hydrothermal method, followed by deposition of Au nanoparticles on GO-MnO2 surface. The prepared nanocomposite was thoroughly characterised by different instrumental techniques such as X-Ray diffraction (XRD),Fourier transform infrared spectroscopy (FTIR),Raman spectroscopy, Field emission scanning electron microscopy (FESEM), Transmission electron microscopy (TEM), High resolution Transmission electron microscopy (HRTEM), X-Ray photo electron spectroscopy (XPS), N-2 adsorption desorption Brunauer-Emmett-Teller (BET) isotherm and Inductively coupled plasma - optical emission spectrometry (ICP-OES). FESEM and TEM images demonstrated that the MnO2 forms rod like structure having diameter of 60-100 nm and are uniformly distributed over the GO surface. HRTEM image clearly signifies gold (Au) nano particles having diameter of 7 +/- 1.9 nm homogeneously distributed throughout the GO-MnO2 surface. Elementary state of Au and tetravalent nature of Mn as well as reduction of functional group after the decoration was confirmed from XPS studies. The catalyst GO-MnO2-Au was found to be the superior catalyst for synthesis of biologically active molecules such as Beni bases and Bisamides. The high catalytic activity of the materials can be attributed to the small and homogeneous distribution of gold nanoparticles, high redox potential of rod shaped MnO2 and the synergistic effect between GO, MnO2 and Au. All the reaction conditions were optimised by varying catalyst dosage, effect of solvent and temperature, The GO-MnO2-Au was easily recycled with minimal leaching and the product yield was found to be 85-90% after 4th cycle demonstrating the stability and durability of our nanocomposite.
• A competent pot and atom-efficient synthesis of Betti bases over nanocrystalline MgO involving a modified Mannich type reaction
  作者：Bikash Karmakar、Julie Banerji

  DOI：10.1016/j.tetlet.2011.07.075

  日期：2011.9

  A simple, efficient, and eco-friendly method for the synthesis of 1-(alpha-aminoalkyl) naphthols, the Betti bases, has been carried out over a basic nanocrystalline MgO catalyst in aqueous condition. The method has been applied for the synthesis of a range of compounds with variable functionalities in excellent yield and selectivity. (C) 2011 Elsevier Ltd. All rights reserved.