methylene di-2-furancarboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: methylene di-2-furancarboxylate
• 英文别名: methylene di-2-furoate；MDF；Furan-2-carbonyloxymethyl furan-2-carboxylate；furan-2-carbonyloxymethyl furan-2-carboxylate
• 化学式: C₁₁H₈O₆
• 分子量: 236.181
• InChiKey: FCBJDZJDELXKNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  糠酸（呋喃甲酸） 、 二氯甲烷 在 potassium carbonate 、 四丁基溴化铵 作用下， 以 水 为溶剂， 反应 3.0h， 生成 methylene di-2-furancarboxylate
  参考文献：
  名称：

  芳族羧酸酯与 1,n-二卤代烷烃直接反应无溶剂合成对称亚甲基二酯

  摘要：

  通过各种芳族羧酸盐与 1, n-二卤代烷烃在无溶剂条件下的直接反应，开发了一种合成对称亚甲基二酯的有效方法。该策略提供了高产率、简便的后处理和纯化，以及一种环境友好的方法来获得具有增加多样性的长链羧酸亚甲酯支架。

  DOI：

  10.1039/d1ra04814g

文献信息

• Dichloromethane as a methylene synthon for regioselective linkage of diverse carboxylic acids: Direct access to methylene diesters under metal-free conditions
  作者：Shuiliang Wang、Zhengjiang Fu、Zhicong Huang、Yongqing Jiang、Shengmei Guo、Hu Cai

  DOI：10.1016/j.cclet.2019.04.053

  日期：2019.6

  Abstract A metal-free cross coupling between common CH2Cl2 and carboxylic acids has been achieved with K2CO3 as the sole additive. This simple protocol is a convenient and cost-effective route to synthesize methylene diesters from a wide scope of carboxylic acids substrates with good functional group tolerance. Several gram-scale reactions have been performed to evaluate the effectiveness and practicality

  摘要以碳酸钾为唯一添加剂，实现了普通二氯甲烷与羧酸之间的无金属交叉偶联。这个简单的协议是从具有良好官能团耐受性的各种羧酸底物合成亚甲基二酯的便捷且经济高效的途径。已经进行了数克级的反应，以评估该协议的有效性和实用性。
• O-Fluoromethyl carboxylates and O-fluoromethyl carbamates
  作者：Manfred Schlosser、Dominique Limat

  DOI：10.1016/0040-4020(95)00251-3

  日期：1995.5

  The fluoride catalyzed reaction between acyl fluorides and monomeric formaldehyde affords fluoromethyl carboxylates in acceptable yields. - Fluoromethyl fluoroformate, readily accessible from the corresponding dichloro compound, condenses with amines to give fluoromethyl carbamates.

  酰基氟与单体甲醛之间的氟化物催化反应以可接受的收率提供了氟甲基羧酸盐。-可容易地从相应的二氯化合物获得的氟甲基氟甲酸酯与胺缩合以得到氟甲基氨基甲酸酯。
• Synthesis of the symmetrical methylene diesters from carboxylic ionic liquids
  作者：D. Gómora-Herrera、I.V. Lijanova、O. Olivares-Xometl、A. Toscano、N.V. Likhanova

  DOI：10.1139/cjc-2017-0042

  日期：2017.7

  The reaction between carboxylic ionic liquids and dichloromethane, which provokes the formation of symmetrical methylene diesters, was carried out. The synthesis of these ionic liquid compounds was carried out in a microwave reactor, and the characterization by spectroscopic techniques of methylene diesters (methylene di-2-furoate, methylene di-2-picolinate, methylene dianthranilate, and methylene dioleate) is described and the crystal structures discussed. The crystal packing of methylene dianthranilate is characterized by trimer formation due to hydrogen bonding via interactions between the hydrogen atom of the primary amine group and the oxygen of the carboxylic group.

  将羧基离子液体与二氯甲烷发生反应，引发对称亚甲基二酯的形成。这些离子液体化合物的合成在微波反应器中进行，并通过光谱技术对亚甲基二酯（亚甲基二-2-呋酸酯、亚甲基二-2-吡啶酸酯、亚甲基二邻氨基苯甲酸酯和亚甲基二油酸酯）进行表征，并讨论晶体结构。亚甲基二邻氨基苯甲酸酯的晶体排列特征是由于氢键作用而形成三聚体，通过主要胺基的氢原子与羧基的氧之间的相互作用。
• Microwave-assisted, facile, rapid and solvent-free one pot two-component synthesis of some special acylals
  作者：Yu-Heng Ma、Gang Wu、Nan Jiang、Shu-Wang Ge、Qian Zhou、Bai-Wang Sun

  DOI：10.1016/j.cclet.2014.11.001

  日期：2015.1

  A facile, rapid and solvent-free method for the conversion of acids and dihalomethane to the corresponding methylene diesters (acylals) using microwave as activators or assistor, is reported. This method is particularly powerful for the diesterification of carboxylic acids, which afford methylene diesters in good to excellent yields (up to >99%). When the intermediate is trapped, a "double successive S(N)2 reactions" mechanism is proved. (C) 2014 Bai-Wang Sun. Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. All rights reserved.
• Electron transfer in the cathodic reduction of α-dicarbonyl compounds
  作者：Belén Batanero、Fructuoso Barba

  DOI：10.1016/j.tet.2007.11.102

  日期：2008.2

  Electron transfer processes take place during the cathodic reduction, under an argon atmosphere, of different alpha-dicarbonyl substrates. Carboxylic acids or methylene diesters are obtained from benzil or furil after electron transfer to the oxygen in the air, during the workup, or after electron transfer to the solvent. Involving an electron transfer to dichloromethane, 2-hydroxy-2-hydroxymethyl-2H-acenaphtylen-1-one or benzo[1,3]dioxin-8-one are formed when acenaphthenequinone or 1,2-cyclohexanedione are, respectively, reduced. (C) 2007 Elsevier Ltd. All rights reserved.