1-(2-hydroxyphenyl)-3-(naphthalen-1-yl)propane-1,3-dione | 179618-17-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(2-hydroxyphenyl)-3-(naphthalen-1-yl)propane-1,3-dione
• 英文别名: 1-(2-Hydroxyphenyl)-3-naphthylpropane-1,3-dione；1-(2-hydroxyphenyl)-3-naphthalen-1-ylpropane-1,3-dione
• CAS: 179618-17-8
• 化学式: C₁₉H₁₄O₃
• 分子量: 290.318
• InChiKey: BEKFAOIUXPWQRV-UHFFFAOYSA-N

物化性质

• 熔点：
  124 °C
• 沸点：
  509.6±30.0 °C(Predicted)
• 密度：
  1.265±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxyphenyl)-3-(naphthalen-1-yl)propane-1,3-dione 在 K₁₀ montmorillonite 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 10H-furo[2,3-a]naphtho[2,1-c]xanthen-10-one
  参考文献：
  名称：

  Transition-Metal-Free Photoinduced Intramolecular Annulation of 2,3-Di(hetero)arylchromen-4-one

  摘要：

  An efficient transition-metal-free photoinduced intracyclization of 4H-chromen-4-ones in EtOH-H2O (7:1, v/v) at ambient temperature for the construction of complicated fused-ring heteroaromatics. is established. The reaction proceeds smoothly without requiring any catalysts/additives.

  DOI：

  10.1021/acs.orglett.7b01531
• 作为产物：
  描述：

  2-acetylphenyl 1-naphthoate 在 吡啶 作用下， 生成 1-(2-hydroxyphenyl)-3-(naphthalen-1-yl)propane-1,3-dione
  参考文献：
  名称：

  以杂多酸为催化剂在甘油中绿色高效合成黄酮和色酮

  摘要：

  菲尔：科伦坡米廖雷罗，玛丽亚贝伦。Consejo Nacional de Investigaciones Cientificas y Tecnicas。Centro Cientifico Tecnologico Conicet - 拉普拉塔。Centro de Investigacion y Desarrollo en Ciencias Aplicadas "Dr. Jorge J. Ronco"。拉普拉塔国立大学。Facultad de Ciencias Exactas。Centro de Investigacion y Desarrollo en Ciencias Aplicadas；阿根廷

  DOI：

  10.2174/1570178615666180509150014

文献信息

• A very simple solvent-free method for the synthesis of 2-arylchromones using KHSO4 as a recyclable catalyst
  作者：María Pérez、Diego Ruiz、Juan Autino、Angel Sathicq、Gustavo Romanelli

  DOI：10.1016/j.crci.2016.02.014

  日期：2016.5

  Résumé An efficient and solvent-free procedure for the synthesis of flavones using KHSO4 as a recyclable catalyst is described. The methodology represents an environmentally friendly process in comprehensive consideration compared with other catalytic systems listed in publications. This method provides a clean, simple, solvent-free reaction and useful alternatives to prepare flavones and chromones. The use of KHSO4 catalyst provides excellent yields, also leading to an easy separation and recovery of the catalysts, which allows both low environmental impact and low cost. Other green advantages of the method are the low formation of wastes and the replacement of corrosive, soluble mineral acids. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.doc

  摘要 本文描述了一种高效无溶剂的黄酮合成程序，采用KHSO4作为可回收催化剂。这种方法在综合考虑下，与其他文献中列出的催化系统相比，代表了一种环保的过程。该方法提供了一种清洁、简单、无溶剂的反应，并为制备黄酮和色酮提供了有用的替代方案。使用KHSO4催化剂可实现优异的产率，同时便于催化剂的分离和回收，这不仅降低了环境影响，还降低了成本。该方法的其他绿色优势包括废物生成少，以及替代腐蚀性可溶性矿酸。 补充材料： 本文章的补充材料作为单独文件提供：mmc1.doc
• Mild and efficient organocatalytic method for the synthesis of flavones
  作者：Filip Stanek、Maciej Stodulski

  DOI：10.1016/j.tetlet.2016.07.042

  日期：2016.8

  A convenient and efficient organocatalytic procedure for the selective cyclization of 1,3-diketones to give aromatic substituted 4H-chromen-4-ones under mild reaction conditions using N-triflyl phosphoramide is described. Application of the described conditions is presented in a formal synthesis of (S)-flavanone.

  描述了一种方便有效的有机催化方法，该方法用于在温和的反应条件下使用N-三氟乙磷酰胺选择性环化1,3-二酮以生成芳族取代的4 H-铬4-酮。所述条件的应用以（S）-黄烷酮的形式合成给出。
• Preyssler catalyst-promoted rapid, clean, and efficient condensation reactions for 3H-1,5-benzodiazepine synthesis in solvent-free conditions
  作者：Gustavo A. Pasquale、Diego M. Ruiz、Jorge L. Jios、Juan C. Autino、Gustavo P. Romanelli

  DOI：10.1016/j.tetlet.2013.09.101

  日期：2013.11

  A simple, convenient, and environmentally benign synthesis of 1,5-benzodiazepines is developed by condensing different o-phenylenediamines and 1,3-aryl-1,3-propanodiones. The reaction is catalyzed by a Preyssler (NaH14P5W30O110, HPA) heteropolyacid as a safe, clean, and recyclable catalyst. The method is operationally simple and provides access to a variety of 1,5-benzodiazepines in good to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.
• Virkar; Shah, Journal of the University of Bombay, Science: Physical Sciences, Mathematics, Biological Sciences and Medicine, 1942, vol. 11/3 A, p. 140
  作者：Virkar、Shah

  DOI：——

  日期：——
• Bennardi, Daniel O.; Romanelli, Gustavo P.; Jios, Jorge L., Heterocyclic Communications, 2007, vol. 13, # 1, p. 77 - 81
  作者：Bennardi, Daniel O.、Romanelli, Gustavo P.、Jios, Jorge L.、Vazquez, Patricia G.、Caceres, Carmen V.、Autino, Juan C.

  DOI：——

  日期：——