[(2-hydroxynaphthalen-1-yl)-(4-hydroxyphenyl)-methyl]urea | 1224571-23-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [(2-hydroxynaphthalen-1-yl)-(4-hydroxyphenyl)-methyl]urea
• 英文别名: [(2-Hydroxynaphthalen-1-yl)-(4-hydroxyphenyl)methyl]urea；[(2-hydroxynaphthalen-1-yl)-(4-hydroxyphenyl)methyl]urea
• CAS: 1224571-23-6
• 化学式: C₁₈H₁₆N₂O₃
• 分子量: 308.337
• InChiKey: JWTFWGXMCIHCOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  95.6
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(2-hydroxynaphthalen-1-yl)-(4-hydroxyphenyl)-methyl]urea 以 N,N-二甲基甲酰胺 为溶剂， 生成 1,2-dihydro-1-(4-hydroxy-phenyl) naphtho [1,2-e][1,3]-oxazin-3-one
  参考文献：
  名称：

  由TMSCl / NaI促进的涉及β-萘酚，醛和尿素的新型三组分单锅反应

  摘要：

  在室温下，在TMSCl / NaI存在下，β-萘酚，芳族醛和尿素的一锅缩合反应可合成高收率的氨基烷基萘酚衍生物。酰胺烷基萘酚衍生物在140℃下闭环，得到1,2-二氢-1-芳基萘[1,2-e] [1,3]恶嗪-3-酮衍生物。J.杂环化​​学。（2010）。

  DOI：

  10.1002/jhet.328
• 作为产物：
  描述：

  对羟基苯甲醛 、 尿素 、 2-萘酚 在 十六烷基三甲基溴化铵 作用下， 以 水 为溶剂， 反应 2.0h， 以86%的产率得到[(2-hydroxynaphthalen-1-yl)-(4-hydroxyphenyl)-methyl]urea
  参考文献：
  名称：

  Cetrimonium Bromide Promoted Efficient Multi-component Protocol for Synthesis of 1-Amidoalkyl-2-naphthols in Aqueous Medium

  摘要：

  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。

  DOI：

  10.14233/ajchem.2021.23251

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。
• Efficient and solvent-free synthesis of 1-amidoalkyl-2-naphthols using N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide
  作者：Ramin Ghorbani-Vaghei、Seyedeh Malaekehpour

  DOI：10.2478/s11532-010-0077-0

  日期：2010.10.1

  N,N,N,’N’ -Tetrabromobenzene-1,3-disulfonamide [TBBDA] is found to be a reusable catalyst for efficient synthesis of various amidoalkyl naphthols from β-naphthol, aromatic aldehydes and urea in good to high yields under solvent-free conditions.

  N，N，N，'N'- 四溴苯-1,3-二磺酰胺[TBBDA]是一种可重复使用的催化剂，可在溶剂下以良好或高收率由β-萘酚，芳族醛和尿素高效合成各种酰胺基烷基萘。无条件。
• Synthesis of 1,2-dihydro-1-arylnaphtho[1,2-e][1,3]oxazine-3-one catalyzed by pyridinium-based ionic liquid
  作者：Fang Dong、Yang Li-fang、Yang Jin-ming

  DOI：10.1007/s11164-012-0776-6

  日期：2013.7

  Some pyridinium-based functionalized ionic liquids have been used as novel catalysts for the synthesis of 1,2-dihydro-1-arylnaphtho[1,2-e][1,3]oxazine-3-one derivatives via the one-pot multi-component condensation of β-naphthol, aromatic aldehydes, and urea under solvent-free conditions, to afford good to excellent yields ranging from 76 to 91 % within 60 min. A possible mechanism to account for the reaction is proposed.

  一些基于吡啶鎓的功能化离子液体已被用作新型催化剂，通过一锅法合成1,2-二氢-1-芳基萘并[1,2-e][1,3]恶嗪-3-酮衍生物。 β-萘酚、芳香醛和脲在无溶剂条件下进行组分缩合，可在 60 分钟内实现从 76 % 到 91 % 的良好收率。提出了解释该反应的可能机制。
• Piper-Betle-Shaped Nano-S-Catalyzed Synthesis of 1-Amidoalkyl-2-naphthols under Solvent-Free Reaction Condition: A Greener “Nanoparticle-Catalyzed Organic Synthesis Enhancement” Approach
  作者：Vijay K. Das、Madhurjya Borah、Ashim J. Thakur

  DOI：10.1021/jo302682k

  日期：2013.4.5

  Nano-S prepared by an annealing process showed excellent catalytic activity for the synthesis of 1-amidoalky1-2-naphthols under solvent-free reaction condition at 50 degrees C. The catalyst could be reused up to the fifth cycle without loss in its action. The green-ness of the present protocol was also measured using green metrics drawing its superiority.
• Physicochemical characterization and catalytic applications of MoO3–ZrO2 composite oxides towards one pot synthesis of amidoalkyl naphthols
  作者：Satish Samantaray、G. Hota、B.G. Mishra

  DOI：10.1016/j.catcom.2011.04.014

  日期：2011.7

  A series of MoO3-ZrO2 composite oxide catalysts were prepared by coprecipitation and impregnation methods and characterized by XRD, Raman, UV-Vis, TEM and sorptometric techniques. Characterization studies indicated the presence of tetragonal zirconia phase and well dispersed MoO3 species as isolated and polymolybdate clusters in the composite oxide. The MoO3(20 mol%)-ZrO2 material was used as efficient catalyst for synthesis of amidoalkyl naphthols under solvent free conditions using conventional as well as microwave heating. The results obtained clearly showed that the composite oxide catalyst was recyclable and highly efficient for the reaction giving good yield and purity of the products.(C) 2011 Elsevier B.V. All rights reserved.