1-((4-methylphenyl)-piperidin-1-yl-methyl)-2-naphthol | 909778-45-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-((4-methylphenyl)-piperidin-1-yl-methyl)-2-naphthol
• 英文别名: 1-[(4-methylphenyl)piperidin-1-ylmethyl]naphthalen-2-ol；1-(4-methylphenyl(piperidine-1-yl)methyl)naphthalen-2-ol；1-(piperidin-1-yl(p-tolyl)methyl)naphthalen-2-ol；1-[(4-Methylphenyl)-piperidin-1-ylmethyl]naphthalen-2-ol；1-[(4-methylphenyl)-piperidin-1-ylmethyl]naphthalen-2-ol
• CAS: 909778-45-6
• 化学式: C₂₃H₂₅NO
• 分子量: 331.458
• InChiKey: XIWLIMALIPBPCG-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：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-((4-methylphenyl)-piperidin-1-yl-methyl)-2-naphthol 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以64.1%的产率得到1-(4-methylbenzyl)naphthalen-2-ol
  参考文献：
  名称：

  Convenient Synthesis of 1‐Arylmethyl‐2‐naphthols

  摘要：

  DOI：

  10.1080/00397910601163547
• 作为产物：
  描述：

  β-四氢萘酮 在 palladium on activated charcoal 三甲基氯硅烷 、 air 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 173.5h， 生成 1-((4-methylphenyl)-piperidin-1-yl-methyl)-2-naphthol
  参考文献：
  名称：

  2-萘酚曼尼希碱的新合成及其核磁共振行为

  摘要：

  开发了一种新的两步程序，包括从 2-四氢萘酮形成 1-亚芳基-2-四氢萘酮，随后在烯酮上添加环状仲胺，然后进行原位空气氧化，以生产 2-萘酚曼尼希碱. 在无溶剂条件下，在对甲苯磺酸存在下，由 2-萘酚和相应的醛类和胺类合成了 2-萘酚曼尼希碱的简单微波辅助一锅法合成。该系列的化合物显示出有趣的 NMR 行为。本文报道了广泛的可变温度 NMR 研究，包括 HSQC 实验。发现溶液相中构象的 NMR 结果与固态中的 X 射线晶体结构一致。

  DOI：

  10.1139/v06-081

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。
• Synthesis of 1‐aminoalkyl‐2‐naphthols derivatives using an engineered copper‐based nanomagnetic catalyst (Fe ₃ O ₄ @CQD@Si (OEt)(CH ₂ ) ₃ NH@CC@N ₃ @phenylacetylene@Cu)
  作者：Tahereh Akbarpour、Ardeshir Khazaei、Jaber Yousefi Seyf、Negin Sarmasti

  DOI：10.1002/aoc.6361

  日期：2021.10

  present study, a molecular level engineered-based method was used to synthesis a copper-based nanomagnetic catalyst (Fe3O4@CQD@Si (OEt)(CH2)3NH@CC@N3@phenylacetylene@Cu). The as-synthesized catalyst was characterized using different techniques, including infrared (IR), X-ray powder diffraction (XRD), field emission scanning electron microscopy (FESEM) and transmission electron microscopy (TEM), energy-dispersive

  在本研究中，基于分子水平的工程化方法用于合成铜基纳米磁性催化剂（Fe 3 O 4 @CQD@Si (OEt)(CH 2 ) 3 NH@CC@N 3 @苯基乙炔@Cu） . 使用不同的技术对合成的催化剂进行表征，包括红外（IR）、X 射线粉末衍射（XRD）、场发射扫描电子显微镜（FESEM）和透射电子显微镜（TEM）、能量色散 X 射线光谱（ EDX) 和 EDX 元素映射、感应耦合等离子体 (ICP)、热重分析 (TGA) 和差热分析 (DTA) 以及振动样品磁强计 (VSM)。Fe 3 O 4使用碳量子点 (CQD) 代替传统的 SiO 2保护纳米粒子表面. 在 1-氨基烷基-2-萘酚衍生物的合成中评估了所合成催化剂的活性。反应时间短、反应收率高的无溶剂条件是所制备催化剂的结果。反应如何被催化剂触发由 IR 确定。合成后的催化剂在五个循环后提供了 87.5% 的反应产率。采用傅里叶变换红外
• 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。
• Magnetic nanocrystallites strontium hexaferrite as an efficient catalyst in the green Betti reaction
  作者：Ghodsi Mohammadi Ziarani、Zhila Kazemi Asl、Parisa Gholamzadeh、Alireza Badiei、Morteza Afshar

  DOI：10.1080/24701556.2019.1574816

  日期：2018.10.3

  The sol-gel auto-combustion method was applied for preparation of SrFe12O19 magnetic nanoparticles (MNPs). Then, the prepared SrFe12O19 was analyzed by VSM, FT-IR, SEM, N-2 adsorption-desorption and XRD pattern. According to the hysteresis loops of SrFe12O19 MNPs, its magnetic saturation was about 79emu/g and also it is a typical feature of ferromagnetic compound. SEM image showed semi-spherical particles with average size of 70nm. The BET surface area of SrFe12O19 MNPs was 10.4m(2)/g. Moreover, the catalytic activity of SrFe12O19 MNPs was tested for the first time toward the Betti reaction. The results showed that it is an efficient catalyst which can be easily separated from the reaction mixture using an external magnet and gives the pure products in high yields within short reaction time.
• 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.