diethyl 2-(3,4,5-trimethoxybenzylidene)malonate | 57724-30-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: diethyl 2-(3,4,5-trimethoxybenzylidene)malonate
• 英文别名: (2,3,4-Trimethoxy-benzylidenmalonsaeure)-diethylester；1,3-Diethyl 2-[(2,3,4-trimethoxyphenyl)methylene]propanedioate；diethyl 2-[(2,3,4-trimethoxyphenyl)methylidene]propanedioate
• CAS: 57724-30-8
• 化学式: C₁₇H₂₂O₇
• 分子量: 338.357
• InChiKey: GLKUOBFVFSOJIX-UHFFFAOYSA-N

物化性质

• 沸点：
  417.8±40.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl 2-(3,4,5-trimethoxybenzylidene)malonate 在 indium(III) chloride 、 sodium hydride 作用下， 以 正己烷 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 2.9h， 生成 4,4-diethyl 5-methyl 6-hydroxy-2-(3,4,5-trimethoxyphenyl)chroman-4,4,5-tricarboxylate
  参考文献：
  名称：

  环丙烷二酯与苯醌酯的 (3 + 3) 和 (3 + 2) 环加成的可切换反应性

  摘要：

  在此，我们描述了一种前所未有的供体-受体环丙烷与醌酯的 (3 + 3) 环加成反应，以中等至良好的收率构建色满支架。有趣的是，该策略还可以调整为 (3 + 2) 环加成，只需切换路易斯酸来提供苯并呋喃支架。根据所用路易斯酸的选择，同一组前体已用于递送苯并吡喃和苯并呋喃衍生物。

  DOI：

  10.1021/acs.orglett.2c03446
• 作为产物：
  描述：

  丙二酸二乙酯 、 2,3,4-三甲氧基苯甲醛 在 哌啶 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 生成 diethyl 2-(3,4,5-trimethoxybenzylidene)malonate
  参考文献：
  名称：

  A Versatile Palladium-Mediated Three-Component Reaction for the One-Pot Synthesis of Stereodefined 3-Arylidene-(or 3-Alkenylidene-)tetrahydrofurans

  摘要：

  A one-pot reaction between equimolecular amounts of various propargyl alcohols, Michael acceptors, and unsaturated halides (or triflates) in the presence of a palladium(0) catalyst provides :a simple and flexible entry into highly substituted 3-arylidene(or 3-alkenylidene)-tetrahydrofurans. The efficiency of this palladium-mediated three-component reaction has been shown to be strongly influenced by the nature of the catalyst system, and in this regard, a palladium(0) catalyst generated in situ by reduction of PdCl2(PPh3)(2) with n-butyllithium has been found particularly effective.

  DOI：

  10.1021/jo0012997

文献信息

• Synthesis and anticonvulsant activity of new 6-methyl-1-substituted-4,6-diazaspiro[2.4]heptane-5,7-diones
  作者：Xianran He、Guanpeng Qiu、Jin Yang、Yuling Xiao、Zhongyuan Wu、Guofu Qiu、Xianming Hu

  DOI：10.1016/j.ejmech.2010.05.034

  日期：2010.9

  In the present study on the development of new anticonvulsants, twenty new 6-methyl-1-substituted-4,6-diazaspiro[2.4]heptane-5,7-diones were synthesized and tested for anticonvulsant activity using the maximal electroshock (MES) and subcutaneous pentylenetetrazole (scPTZ) screens. Their neurotoxicity was determined by the rotorod test. In this series, all of the alkyl- and aryl-substituted 5,5-cyclo-propanespirohydantoins showed more or less protection against MES and/or scPTZ models. The most active of the series was 6-methyl-1-(4-(methylsulfonyl)phenyl)-4,6-diazaspiro[2.4]heptane-5,7-dione (6t), which showed a MES ED50 value of 12.5 mg/kg in mice. The median toxic dose (TD50) was 310 mg/kg, providing compound 6t with a protection index (PI = TD50/ED50) of 24.8 in the MES test which is better than phenytoin. (C) 2010 Elsevier Masson SAS. All rights reserved.
• A Versatile Palladium-Mediated Three-Component Reaction for the One-Pot Synthesis of Stereodefined 3-Arylidene-(or 3-Alkenylidene-)tetrahydrofurans
  作者：Marilyn Bottex、Marcello Cavicchioli、Benoît Hartmann、Nuno Monteiro、Geneviève Balme

  DOI：10.1021/jo0012997

  日期：2001.1.1

  A one-pot reaction between equimolecular amounts of various propargyl alcohols, Michael acceptors, and unsaturated halides (or triflates) in the presence of a palladium(0) catalyst provides :a simple and flexible entry into highly substituted 3-arylidene(or 3-alkenylidene)-tetrahydrofurans. The efficiency of this palladium-mediated three-component reaction has been shown to be strongly influenced by the nature of the catalyst system, and in this regard, a palladium(0) catalyst generated in situ by reduction of PdCl2(PPh3)(2) with n-butyllithium has been found particularly effective.
• Switchable Reactivity of Cyclopropane Diesters toward (3 + 3) and (3 + 2) Cycloadditions with Benzoquinone Esters
  作者：Navpreet Kaur、Pankaj Kumar、Arijit Hazra、Prabal Banerjee

  DOI：10.1021/acs.orglett.2c03446

  日期：2022.11.11

  Herein, we describe an unprecedented (3 + 3) cycloaddition reaction of the donor–acceptor cyclopropanes with quinone esters toward the construction of chroman scaffolds in moderate to good yields. Interestingly, the strategy is also adjustable toward a (3 + 2) cycloaddition by just switching the Lewis acid to furnish benzofuran scaffolds. Based on the choice of Lewis acid used, the same set of precursors

  在此，我们描述了一种前所未有的供体-受体环丙烷与醌酯的 (3 + 3) 环加成反应，以中等至良好的收率构建色满支架。有趣的是，该策略还可以调整为 (3 + 2) 环加成，只需切换路易斯酸来提供苯并呋喃支架。根据所用路易斯酸的选择，同一组前体已用于递送苯并吡喃和苯并呋喃衍生物。