N-(furan-2-yl(2-hydroxynaphthalen-1-yl)methyl)benzamide | 423730-04-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(furan-2-yl(2-hydroxynaphthalen-1-yl)methyl)benzamide
• 英文别名: N-[furan-2-yl-(2-hydroxynaphthalen-1-yl)methyl]benzamide
• CAS: 423730-04-5
• 化学式: C₂₂H₁₇NO₃
• 分子量: 343.382
• InChiKey: OFZKDWROJWDFHK-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：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  62.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  糠醛 、 苯甲酰胺 、 2-萘酚 在 montmorillonite (K₁₀) loaded on magnetite silica-coated nanoparticle 作用下， 以 neat (no solvent) 为溶剂， 以96 %的产率得到N-(furan-2-yl(2-hydroxynaphthalen-1-yl)methyl)benzamide
  参考文献：
  名称：

  Magnetite-supported montmorillonite (K₁₀) (nanocat-Fe-Si-K₁₀): an efficient green catalyst for multicomponent synthesis of amidoalkyl naphthol

  摘要：

  蒙脱石（K10）负载在磁铁矿二氧化硅涂层纳米粒子上，是通过简单的共沉淀方法制成的。

  DOI：

  10.1039/d3ra01522j

文献信息

• One-pot three-component synthesis of 1-amidoalkyl naphthols and polyhydroquinolines using a deep eutectic solvent: a green method and mechanistic insight
  作者：Vu Thanh Nguyen、Hai Truong Nguyen、Phuong Hoang Tran

  DOI：10.1039/d0nj05687a

  日期：——

  The multicomponent synthesis of 1-amidoalkyl naphthols and polyhydroquinolines has been developed as an atom-economic procedure catalyzed by a deep eutectic solvent ([CholineCl][ZnCl2]3). The reactions proceed smoothly at low temperatures for a short reaction time without the use of toxic and volatile organic solvents. Deep eutectic solvents are capable of not only allowing multicomponent reactions

  作为一种由深共熔溶剂（[CholineCl] [ZnCl 2 ] 3）催化的原子经济方法，已经开发了1-酰胺基烷基萘酚和聚氢喹啉的多组分合成方法。反应在低温下可在短时间内反应平稳进行，而无需使用有毒和挥发性的有机溶剂。深共晶溶剂不仅能够使多组分反应以高收率进行，而且能够控制对所需产物的选择性。该机制的见解由HRMS（ESI）进行了审查，以提出一个合理的机制。此外，[CholineCl] [ZnCl 2 ] 3可以在最优化的条件下以多达三个连续循环的方式循环利用，而催化活性的损失却很小。
• Cetrimonium Bromide Promoted Efficient Multi-component Protocol for Synthesis of 1-Amidoalkyl-2-naphthols in Aqueous Medium
  作者：A.V. Nakhate、A.P. Ingale、S.V. Shinde

  DOI：10.14233/ajchem.2021.23251

  日期：——

  An efficient and eco-friendly cetrimonium bromide promoted one-pot synthesis of 1-amidoalkyl-2-naphthols by the multicomponent condensation of aldehydes, β-naphthol and amides in water is reported. The wide range of substrate scope, excellent yield, short reaction rate, operational simplicity and environmentally friendly water as medium are the prominent feature of this protocol.

  一种高效、环保的溴化十六烷基铵催化的一锅法合成1-酰胺烷基-2-萘酚的方法报道了在水中进行醛、β-萘酚和酰胺的多组分缩合反应。该方法的显著特点包括广泛的底物范围、优异的产率、短的反应时间、操作简便以及环保的水介质。
• [MeC(OH)2]+ClO4-: A New Efficient Organocatalyst for the Preparation of 1-Amido- and 1-Carbamato-alkyl Naphthols
  作者：Fatemeh Tamaddon、Javad Bistgani

  DOI：10.1055/s-0031-1289906

  日期：2011.12

  [MeC(OH)2]+ClO4 - as a super acidic ionic liquid is found to be a new and highly efficient catalyst in the synthesis of amidoalkyl naphthols via three-component condensation of β-naphthol and aldehydes with nitriles, amides, or carbamates. multicomponent reactions - amidoalkyl naphthols - ionic liquids - super acids

  [的MeC（OH）2 ] + CLO 4 -作为超级酸性离子液体被发现是在酰氨基烷基萘酚的合成一个新的和高效的催化剂经由β萘酚的三组分缩合和醛与腈，酰胺，或氨基甲酸酯。 多组分反应-酰胺基烷基萘酚-离子液体-超强酸
• 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-Fe3O4)，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 Fe3O4 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 Fe3O4 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。
• Strontium(II) Triflate Catalysed Condensation of β-Naphthol, Aldehyde and Urea or Amides: A Facile Synthesis of Amidoalkyl Naphthols
  作者：Weike Su、Wenyuan Tang、Jianjun Li

  DOI：10.3184/030823408x298508

  日期：2008.3

  A novel and efficient synthesis of amidoalkyl naphthols has been developed by one-pot condensation of β-naphthol, aromatic aldehydes and urea or amides in the presence of strontium(II) triflate as a catalyst in high yields.

  在三氟甲磺酸锶 (II) 作为催化剂的存在下，通过 β-萘酚、芳香醛和尿素或酰胺的一锅缩合，开发了一种新型高效的酰氨基烷基萘酚合成方法。