Diethyl 2,6-dimethyl-4-(3-nitrophenyl)-4H-pyran-3,5-dicarboxylate | 188357-88-2

• 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: Diethyl 2,6-dimethyl-4-(3-nitrophenyl)-4H-pyran-3,5-dicarboxylate
• CAS: 188357-88-2
• 化学式: C₁₉H₂₁NO₇
• 分子量: 375.378
• InChiKey: BUFGEPZFPXRKLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Diethyl 2,6-dimethyl-4-(3-nitrophenyl)-4H-pyran-3,5-dicarboxylate 在 四乙基溴化铵 、 水 、 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以40%的产率得到5-(ethoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-4H-pyran-3-carboxylic acid
  参考文献：
  名称：

  Optimization of the Selective Monohydrolysis of Diethyl 4-Aryl-4H-pyran-3,5-dicarboxylates

  摘要：

  本研究介绍了一种在季铵盐催化条件下选择性单水解 2,6-二甲基-4-芳基-4H-吡喃-3,5-二甲酸二乙酯的简单、高效且环保的方法。使用不同摩尔比的 NaOH 和水-有机溶剂混合物研究了各种季铵盐的催化活性。结果表明，在 10%的水-乙醇介质中，温度为 40 °C，将 1.0 等量的四乙基溴化铵 (TEAB) 与 1.2 等量的 NaOH 混合使用，对 2,6-二甲基-4-芳基-4H-吡喃-3,5-二甲酸二乙酯的单水解具有显著的选择性。在优化的条件下，一系列 4-芳基-4H-吡喃-3,5-二羧酸酯的单水解反应得到了相应的单酯，产率达到 20-80%，证明了该工艺的实用性。

  DOI：

  10.3390/molecules16053845
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 间硝基苯甲醛 在 zinc(II) chloride 作用下， 以 乙酸酐 为溶剂， 反应 0.67h， 以84.9%的产率得到Diethyl 2,6-dimethyl-4-(3-nitrophenyl)-4H-pyran-3,5-dicarboxylate
  参考文献：
  名称：

  Improved synthesis of diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylate under ultrasound irradiation

  摘要：

  Diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylates (1) have been synthesized by the reaction of aryl aldehyde and 1,3-diketone catalyzed by ZnCl2 under ultrasound irradiation. The effects of changes in the ultrasonic power, temperature, and reaction time are discussed. With the optimized reaction conditions, various aryl aldehydes were used to synthesize 4H-pyrans (1) under the influence of ultrasound irradiation. Compared with the conventional thermal methods, the remarkable advantages of this method are the simple experimental procedure, shorter reaction time and high yield of product. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2009.09.006

文献信息

• Improved synthesis of diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylate under ultrasound irradiation
  作者：Cheng-Liang Ni、Xiao-Hui Song、Hong Yan、Xiu-Qing Song、Ru-Gang Zhong

  DOI：10.1016/j.ultsonch.2009.09.006

  日期：2010.2

  Diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylates (1) have been synthesized by the reaction of aryl aldehyde and 1,3-diketone catalyzed by ZnCl2 under ultrasound irradiation. The effects of changes in the ultrasonic power, temperature, and reaction time are discussed. With the optimized reaction conditions, various aryl aldehydes were used to synthesize 4H-pyrans (1) under the influence of ultrasound irradiation. Compared with the conventional thermal methods, the remarkable advantages of this method are the simple experimental procedure, shorter reaction time and high yield of product. (C) 2009 Elsevier B.V. All rights reserved.
• SnCl2/nano SiO2: A green and reusable heterogeneous catalyst for the synthesis of polyfunctionalized 4H-pyrans
  作者：Javad Safaei-Ghomi、Raheleh Teymuri、Hossein Shahbazi-Alavi、Abolfazl Ziarati

  DOI：10.1016/j.cclet.2013.06.021

  日期：2013.10

  A highly efficient and general method for the synthesis of polyfunctionalized 4H-pyrans is established through a one-pot multicomponent cyclocondensation of aromatic aldehydes with CH acids, malononitrile and ethyl acetoacetate using nano silica supported tin (II) chloride as a catalyst. In this method SnCl2/nano SiO2 was used as green and reusable catalyst. Excellent yields, short reaction times, simple workup, and inexpensiveness and commercially availability of the catalyst are the advantages of this method. (C) 2013 Javad Safaei-Ghomi. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• Optimization of the Selective Monohydrolysis of Diethyl 4-Aryl-4H-pyran-3,5-dicarboxylates
  作者：Jiaojiao Duan、Xiaohui Song、Hong Yan、Xiuqing Song

  DOI：10.3390/molecules16053845

  日期：——

  A simple, efficient and eco-friendly procedure for the selective monohydrolysis of diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylates under quaternary ammonium salt catalysis conditions is presented. The catalytic activities of various quaternary ammonium salts were investigated using different molar ratios of NaOH and water-organic solvent mixtures. The results indicate that the combination of 1.0 equivalent of tetraethyl-ammonium bromide (TEAB) with 1.2 equivalents of NaOH in a 10% water-ethanol media at 40 °C displays remarkable selectivity for the monohydrolysis of diethyl 2,6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylates. The utility of this process is demonstrated by the monohydrolysis of a series of 4-aryl-4H-pyran-3,5-dicarboxylate esters to afford the corresponding monoesters in 20–80% yields under the optimized conditions.

  本研究介绍了一种在季铵盐催化条件下选择性单水解 2,6-二甲基-4-芳基-4H-吡喃-3,5-二甲酸二乙酯的简单、高效且环保的方法。使用不同摩尔比的 NaOH 和水-有机溶剂混合物研究了各种季铵盐的催化活性。结果表明，在 10%的水-乙醇介质中，温度为 40 °C，将 1.0 等量的四乙基溴化铵 (TEAB) 与 1.2 等量的 NaOH 混合使用，对 2,6-二甲基-4-芳基-4H-吡喃-3,5-二甲酸二乙酯的单水解具有显著的选择性。在优化的条件下，一系列 4-芳基-4H-吡喃-3,5-二羧酸酯的单水解反应得到了相应的单酯，产率达到 20-80%，证明了该工艺的实用性。