N-[(3-bromophenyl)-(2-hydroxynaphth-1-yl)methyl]benzamide | 1402928-59-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[(3-bromophenyl)-(2-hydroxynaphth-1-yl)methyl]benzamide
• 英文别名: N-[(3-bromophenyl)-(2-hydroxynaphthalen-1-yl)methyl]benzamide
• CAS: 1402928-59-9
• 化学式: C₂₄H₁₈BrNO₂
• 分子量: 432.316
• InChiKey: SCPWULMZXNORFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  间溴苯甲醛 、 苯甲酰胺 、 2-萘酚 在 Homopiperazine sulfamic acid functionalized mesoporous silica nanoparticles 作用下， 以 neat (no solvent) 为溶剂， 反应 1.75h， 以86%的产率得到N-[(3-bromophenyl)-(2-hydroxynaphth-1-yl)methyl]benzamide
  参考文献：
  名称：

  均哌嗪氨基磺酸官能化的介孔二氧化硅纳米粒子（MSNs-HPZ-SO 3 H）作为一锅合成1-酰胺基-2-萘的有效催化剂

  摘要：

  介孔二氧化硅纳米粒子被高哌嗪氨基磺酸有效地官能化。所得的MSNs-HPZ-SO 3 H在热溶剂-下，通过芳族醛，酰胺/脲和β-萘酚的三组分缩合反应，被用作一锅合成1-酰胺烷基-2-萘的纳米催化剂。免费条件。催化剂的表征使用XRD，SEM，FT-IR，TGA-DTA和氮吸附-解吸分析进行。该方案被开发为一种利用生态友好型催化剂合成1-氨基烷基-2-萘酚的安全便捷的替代方法。

  DOI：

  10.1039/c5nj02974k

文献信息

• Efficient One-Pot Syntheses of Betti Bases Catalyzed by 1-Methyl-3-(2-(sulfooxy)ethyl)-1<i>H</i>-imidazol-3-ium Chloride
  作者：C. Wang、Y. Wan、H.-Y. Wang、L.-L. Zhao、J.-J. Shi、X.-X. Zhang、H. Wu

  DOI：10.1002/jhet.1124

  日期：2013.5

  The efficient one‐pot syntheses of Betti bases by the three‐component reaction of aromatic aldehyde, 2‐naphthalen, and acetonitrile (or benzamide) catalyzed by 1‐methyl‐3‐(2‐(sulfooxy)ethyl)‐1H‐imidazol‐3‐ium chloride is reported. The solvent can be recycled easily.

  通过1-甲基-3-（2-（磺氧基）乙基）-1H-咪唑催化的芳香醛，2-萘和乙腈（或苯甲酰胺）的三组分反应有效地一锅合成Betti碱报道了氯化三 该溶剂可以容易地回收。
• Graphite-Supported Perchloric Acid (HClO4-C): An Efficient and Recyclable Heterogeneous Catalyst for the One-Pot Synthesis of Amidoalkyl Naphthols
  作者：Zhen-Kai Lei、Li Xiao、Xiao-Quan Lu、He Huang、Chen-Jiang Liu

  DOI：10.3390/molecules18021653

  日期：——

  An efficient and direct protocol for the preparation of amidoalkylnaphthols employing a multi-component, one-pot condensation reaction of 2-naphthol, aromatic aldehydes and acetamide or benzamide in the presence of graphite supported perchloric acid under solvent-free conditions is described. The thermal solvent-free procedure offers advantages such as simple work-up, shorter reaction times and higher product yields, and the catalyst exhibited remarkable reactivity and can be recycled.

  本文描述了一种高效的直接合成酰胺烷基萘酚的协议，该协议采用了多组分一锅法冷凝反应，反应物为2-萘酚、芳香醛和醋酰胺或苯酰胺，在无溶剂条件下使用石墨支持的高氯酸作为催化剂。该热无溶剂程序提供了优点，如简单的后处理、更短的反应时间和更高的产物收率，催化剂表现出显著的反应性，并且可以重复使用。
• A novel inorganic–organic nanohybrid material H₄SiW₁₂O₄₀/pyridino-MCM-41 as efficient catalyst for the preparation of 1-amidoalkyl-2-naphthols under solvent-free conditions
  作者：R. Tayebee、M. M. Amini、M. Akbari、A. Aliakbari

  DOI：10.1039/c5dt00368g

  日期：——

  A new inorganic–organic nanohybrid material was prepared and performed as an efficient catalyst for the one-pot multi-component synthesis of different substituted 1-amidoalkyl-2-naphthols under solvent-free conditions.

  一种新的无机-有机纳米杂化材料被制备并作为高效催化剂，用于在无溶剂条件下一锅法合成不同取代的1-酰胺烷基-2-萘酚。
• Synthesis, characterization and application of 3‐methyl‐1‐sulfonic acid imidazolium tetrachloroferrate as nanostructured catalyst for the tandem reaction of <i>β</i> ‐naphthol with aromatic aldehydes and amide derivatives
  作者：Ardeshir Khazaei、Ahmad Reza Moosavi‐Zare、Saeed Firoozmand、Mohammad Reza Khodadadian

  DOI：10.1002/aoc.4058

  日期：2018.2

  3‐methyl‐1‐sulfonic acid imidazolium tetrachloroferrate [Msim]FeCl4} was prepared and fully characterized by fourier transform infrared spectroscopy (FT‐IR), X‐ray diffraction (XRD), thermal gravimetric analysis (TGA), differential thermal gravimetric (DTG), field emission scanning electron microscopy (FESEM), energy dispersive X‐ray analysis (EDX) and vibrating sample magnetometer (VSM) and used

  制备了3-甲基-1-磺酸四氯高铁酸咪唑鎓盐[[Msim] FeCl 4 }，并通过傅里叶变换红外光谱（FT-IR），X射线衍射（XRD），热重分析（TGA），差热重量法（DTG），场发射扫描电子显微镜（FESEM），能量色散X射线分析（EDX）和振动样品磁力计（VSM），并用作有效的催化剂，用于β-萘酚与芳族醛和苯甲酰胺在110°C的无溶剂条件下以高收率和非常短的反应时间生成1-酰胺基烷基-2-萘酚。
• Preparation and characterization of a novel Wells–Dawson heteropolyacid-based magnetic inorganic–organic nanohybrid catalyst H₆P₂W₁₈O₆₂/pyridino-Fe₃O₄for the efficient synthesis of 1-amidoalkyl-2-naphthols under solvent-free conditions
  作者：Reza Tayebee、Mostafa M. Amini、Hooriyeh Rostamian、Azam Aliakbari

  DOI：10.1039/c3dt51594j

  日期：——

  A novel magnetic inorganic–organic nanohybrid material H6P2W18O62/pyridino-Fe3O4 (HPA/TPI-Fe3O4) was fabricated and performed as an efficient, eco-friendly, and highly recyclable catalyst for the solvent-free, one-pot, and multi-component synthesis of various substituted 1-amidoalkyl-2-naphthols from the reaction of β-naphthol, an aldehyde, and benzamide with good to excellent yields (47–94%) and in a short span of time (25–60 min). The nanohybrid catalyst was prepared by the chemical anchoring of Wells–Dawson heteropolyacid H6P2W18O62 onto the surface of modified Fe3O4 nanoparticles with N-[3-(triethoxysilyl)propyl]isonicotinamide (TPI) linker. The magnetically recoverable catalyst was easily recycled at least eight times without any loss of catalytic activity. XRD, TEM, UV-vis, and FTIR confirmed that the heteropolyacid H6P2W18O62 is well dispersed on the surface of the solid support and its structure is retained after immobilization on the pyridine modified Fe3O4 nanoparticles. This protocol is developed as a safe and convenient alternate method for the synthesis of 1-amidoalkyl-2-naphthols utilizing an eco-friendly, and a highly reusable catalyst.

  制备了一种新型磁性无机-有机纳米杂化材料H6P2W18O62/吡啶基-Fe3O4 (HPA/TPI- )，并作为一种高效、环保、高度可回收的催化剂，用于无溶剂、一锅法和多用途催化剂。由β-萘酚、醛和苯甲酰胺反应合成各种取代的 1-酰胺基烷基-2-萘酚，产率从良好到优异 (47-94%)，且时间跨度短（25-60 分钟） ）。该纳米杂化催化剂是通过将 Wells-Dawson 杂多酸 H6P2W18O62 化学锚定到带有 N-[3-(三乙氧基甲硅烷基)丙基]异烟酰胺 (TPI) 连接体的改性 纳米颗粒表面来制备的。可磁性回收的催化剂可以轻松回收至少八次，而不会损失任何催化活性。 XRD、TEM、UV-vis 和 FTIR 证实杂多酸 H6P2W18O62 良好分散在固体载体表面，固定在吡啶修饰的 纳米粒子上后其结构保留。该方案被开发为一种安全、方便的替代方法，利用环保且高度可重复使用的催化剂合成 1-酰胺基烷基-2-萘酚。