2-(3',4'-dimethoxyphenyl)-3-(ethoxycarbonyl)-4-methyl-2,5-dihydrofuran

• 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: 2-(3',4'-dimethoxyphenyl)-3-(ethoxycarbonyl)-4-methyl-2,5-dihydrofuran
• 英文别名: Ethyl 2-(3,4-dimethoxyphenyl)-4-methyl-2,5-dihydrofuran-3-carboxylate；ethyl 2-(3,4-dimethoxyphenyl)-4-methyl-2,5-dihydrofuran-3-carboxylate
• 化学式: C₁₆H₂₀O₅
• 分子量: 292.332
• InChiKey: CDFVPRYZKLNOQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl (E)-3,4-dimethoxycinnamate 在 ammonium cerium(IV) nitrate 、 偶氮二异丁腈 、 lithium bromide 、 N-ethylpiperidinium hypophosphite 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 28.0h， 生成 2-(3',4'-dimethoxyphenyl)-3-(ethoxycarbonyl)-4-methyl-2,5-dihydrofuran
  参考文献：
  名称：

  Esteves, Ana P.; Lemos, Maria A.; Medeiros, Maria J., Journal of Chemical Research, 2004, # 6, p. 381 - 383

  摘要：

  DOI：

文献信息

• Electroreductive Intramolecular Cyclization of a Bromo Propargyloxy Ester Catalyzed by Nickel(I) Tetramethylcyclam Electrogenerated at Carbon Cathodes in Dimethylformamide
  作者：Ana P. Esteves、Danielle M. Goken、Lee J. Klein、Maria A. Lemos、Maria J. Medeiros、Dennis G. Peters

  DOI：10.1021/jo026102k

  日期：2003.2.1

  Cyclic voltammetry and controlled-potential electrolysis have been employed to investigate and characterize the reductive intramolecular cyclization of ethyl 2-bromo-3-(3',4'-dimethoxyphenyl)-3-(propargyloxy)propanoate (1) promoted by (1,4,8,11-tetramethyl-1,4,8,11-tetraazacyclotetradecane)nickel(I), [Ni(tmc)](+), electrogenerated at glassy carbon cathodes in dimethylformamide containing tetraalkylammonium

  循环伏安法和控制电位电解已用于研究和表征由（1， 4,8,11-四甲基-1,4,8,11-四氮杂环十四烷）镍（I）[Ni（tmc）]（+）在含四烷基铵盐的二甲基甲酰胺中的玻璃碳阴极上电生成。在1存在下还原[Ni（tmc）]（2+）的循环伏安图显示，[Ni（tmc）]（+）催化还原1的电势比直接还原1所需的电势更正。含[Ni（tmc）]（2+）和1的溶液的电位电解 后者的催化还原通过碳-溴键的单电子裂解形成自由基中间体而进行环化后得到2-（3'，4'-二甲氧基苯基）-3-（乙氧基羰基）-4-亚甲基四氢呋喃（2 ）。在碱的存在下（无论是电生成的还是有意添加为叔丁醇钾），2均会重排以生成2-（3'，4'-二甲氧基苯基）-3-（乙氧基羰基）-4-甲基-2,5-二氢呋喃（3）。提出了一种机械方案来解释通过循环伏安法和控制电位电解所获得的结果。-二甲氧基苯基）-3-（乙氧基羰基）-4-甲基-2,5-二
• Electrochemical Catalytic Cyclization Reactions Using Environmentally Friendly Methodologies
  作者：E. Duñach、M. J. Medeiros、S. Olivero

  DOI：10.1149/2.016307jes

  日期：——

  The electrochemical intramolecular cyclisation of bromoalkoxylated derivatives 1 was carried out using Ni(II) complexes as the catalysts in ethanol solutions by constant-current electrolysis in one-compartment cell in the absence of sacrificial anodes as an environmentally friendly system. The reduction of the substrates proceeds via one-electron cleavage of the carbon–bromine bond to form radical-type

  溴烷氧基化衍生物 1 的电化学分子内环化是使用 Ni(II) 配合物作为催化剂在乙醇溶液中通过恒流电解在没有牺牲阳极作为环境友好系统的单室电池中进行的。底物的还原通过碳 - 溴键的单电子裂解进行，形成自由基型中间体，这些中间体经过环化以中等至良好的产率提供环醚。
• Catalytic Cyclization of Propargyl Bromoethers via Electrogenerated Nickel(I) Tetramethylcyclam in Ionic Liquids: Water Effects
  作者：J. P. Mendes、E. Duñach、J. M. S. S. Esperança、M. J. Medeiros、J. F. Ribeiro、M. M. Silva、S. Olivero

  DOI：10.1149/2.1171904jes

  日期：——

  Cyclic voltammetry and controlled-potential electrolysis have been employed to investigate the reductive intramolecular cyclization of propargyl bromoethers derivatives, catalyzed by electrogenerated (1,4,8,11-tetramethyl-1,4,8,11-tetraaza-cyclotetradecane) nickel(I), [Ni(tmc)](+), as the catalyst, in N,N,N-trimethyl-N-(2-hydroxyethyl) ammonium bis(trifluoromethylsulfonyl) imide, [N-1 1 1 2(OH)][NTf2] and 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl) imide, [C(2)mim][NTf2] in the absence and in the presence of water. The results show that the reaction leads to the formation of the expected heterocyclic compounds, in moderate to good yields. These compounds are important intermediates in the synthesis of natural products with possible biological activities. (C) 2019 The Electrochemical Society.