3-hydroxy-5-methyl-2,3-dihydrofuran-3,4-dicarboxylic acid diethyl ester | 1048023-88-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-hydroxy-5-methyl-2,3-dihydrofuran-3,4-dicarboxylic acid diethyl ester
• 英文别名: diethyl 3-hydroxy-5-methyl-2H-furan-3,4-dicarboxylate
• CAS: 1048023-88-6
• 化学式: C₁₁H₁₆O₆
• 分子量: 244.244
• InChiKey: GCEDRVQOYISHSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-hydroxy-5-methyl-2,3-dihydrofuran-3,4-dicarboxylic acid diethyl ester 在 1-甲基-3-戊基溴化咪唑 作用下， 反应 4.0h， 以90%的产率得到diethyl 2-methylfuran-3,4-dicarboxylate
  参考文献：
  名称：

  Ionic liquid promoted interrupted Feist–Benary reaction with high diastereoselectivity

  摘要：

  A basic ionic liquid, 1-butyl-3-methylimidazolium hydroxide promotes the interrupted Feist-Eenary reaction at room temperature under organic solvent-ftee conditions to produce a variety of substituted hydFOxydihydrofurans. The hydroxydihydrofurans are converted to furans (Feist-Benary products) using the ionic liquid, 1-methyl-3-pentylimidazolium bromide at 70-75 degrees C. The reactions are very clean, high yielding and highly stereoselective. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.083
• 作为产物：
  描述：

  3-溴丙酮酸乙酯 、 乙酰乙酸乙酯 在 1-butyl-3-methylimidazolium hydroxide 作用下， 反应 1.5h， 以80%的产率得到3-hydroxy-5-methyl-2,3-dihydrofuran-3,4-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  Ionic liquid promoted interrupted Feist–Benary reaction with high diastereoselectivity

  摘要：

  A basic ionic liquid, 1-butyl-3-methylimidazolium hydroxide promotes the interrupted Feist-Eenary reaction at room temperature under organic solvent-ftee conditions to produce a variety of substituted hydFOxydihydrofurans. The hydroxydihydrofurans are converted to furans (Feist-Benary products) using the ionic liquid, 1-methyl-3-pentylimidazolium bromide at 70-75 degrees C. The reactions are very clean, high yielding and highly stereoselective. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.05.083

文献信息

• Synthesis of chiral dihydrofuran compounds by thiourea derivatives-catalyzed “interrupted” Feist-Bénary reaction
  作者：Hui Chen、Ru Jiang、Qiao Feng Wang、Xiao Li Sun、Jing Luo、Sheng Yong Zhang

  DOI：10.1016/j.cclet.2009.10.012

  日期：2010.2

  study, six thiourea derivatives of cinchona alkaloids with 9-nat or 9-epi-configuration were synthesized. After characterized the structures, we adopted them to the asymmetric “interrupted” Feist-Bénary (IFB) reaction of α-haloketones with β-dicarbonyl compounds, to give optically active dihydrofurans. Various thiourea derivatives as organocatalysts were examined. The corresponding chiral hydroxyl dihydrofurans

  在这项研究中，合成了具有9-nat或9-epi构型的金鸡纳生物碱的6种硫脲衍生物。对结构进行表征后，我们将其用于α-卤代酮与β-二羰基化合物的不对称“中断”Feist-Bénary（IFB）反应，从而生成光学活性的二氢呋喃。研究了各种硫脲衍生物作为有机催化剂。以优异的产率和中等的ee获得了相应的手性羟基二氢呋喃。对于无环底物，我们获得了令人鼓舞和有希望的结果。
• Ionic liquid promoted interrupted Feist–Benary reaction with high diastereoselectivity
  作者：Brindaban C. Ranu、Laksmikanta Adak、Subhash Banerjee

  DOI：10.1016/j.tetlet.2008.05.083

  日期：2008.7

  A basic ionic liquid, 1-butyl-3-methylimidazolium hydroxide promotes the interrupted Feist-Eenary reaction at room temperature under organic solvent-ftee conditions to produce a variety of substituted hydFOxydihydrofurans. The hydroxydihydrofurans are converted to furans (Feist-Benary products) using the ionic liquid, 1-methyl-3-pentylimidazolium bromide at 70-75 degrees C. The reactions are very clean, high yielding and highly stereoselective. (c) 2008 Elsevier Ltd. All rights reserved.