Dimethyl furfurylmalonate | 99187-02-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Dimethyl furfurylmalonate
• 英文别名: dimethyl (furan-2-ylmethyl)propanedioate；furfuryl-malonic acid dimethyl ester；Furfuryl-malonsaeure-dimethylester；1,3-Dimethyl 2-(furan-2-ylmethyl)propanedioate；dimethyl 2-(furan-2-ylmethyl)propanedioate
• CAS: 99187-02-7
• 化学式: C₁₀H₁₂O₅
• mdl: MFCD24842845
• 分子量: 212.202
• InChiKey: ADKNNRSNACQMOB-UHFFFAOYSA-N

物化性质

• 沸点：
  265.5±25.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Dimethyl furfurylmalonate 在 甲醇 、 硫酸 作用下， 生成 (2,5-dimethoxy-2,5-dihydro-furfuryl)-malonic acid dimethyl ester
  参考文献：
  名称：

  Elming, Acta Chemica Scandinavica (1947), 1956, vol. 10, p. 1664

  摘要：

  DOI：
• 作为产物：
  描述：

  在 四(三苯基膦)钯 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 5.5h， 生成 Dimethyl furfurylmalonate
  参考文献：
  名称：

  Chemistry of 3,4-epoxy-2-methylene oxolanes: A new synthesis of furanes and dihydrofuranes

  摘要：

  Dihydrofurans were obtained by selective 1,4-nucleophilic additions to 3,4-epoxy-2-methylene oxolanes(EMO). Aromatization gave the corresponding substituted furans. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)00442-x

文献信息

• Mauleon, Pablo; Zeldin, Rachel M.; Gonzalez, Ana Z., Journal of the American Chemical Society, 2009, vol. 131, p. 6348 - 6349
  作者：Mauleon, Pablo、Zeldin, Rachel M.、Gonzalez, Ana Z.、Toste, F. Dean

  DOI：——

  日期：——
• Cyclization Reactions of 2,3-Bis(phenylsulfonyl)-1,3-butadiene with Various Carbanions. A [4 + 1] Anionic Annulation Approach to Phenylsulfonyl-Substituted Cyclopentenes
  作者：Albert Padwa、Michelle A. Filipkowski、Michael Meske、S. Shaun Murphree、Scott H. Watterson、Zhijie Ni

  DOI：10.1021/jo00082a015

  日期：1994.2

  2,3-Bis(phenylsulfonyl)-1,3-butadiene undergo es conjugate addition in the presence of carbanions giving rise to a variety of unsaturated sulfones. Reaction with lithium enolates proceeds via an allylic anionic intermediate which undergoes a subsequent elimination of phenylsulfinate anion to produce an allene. Generation of enolates from silyl enol ethers results in conjugate addition to the diene without subsequent elimination. Substituted cyclopentenyl sulfones are available via a [4 + 1] annulation reaction of the diene with various distabilized carbanions. The reaction involves a tandem addition-proton exchange-addition sequence. In the special case of 2,4-pentanedione, pyrans are formed, the isomeric identity of which depends upon the reaction conditions. 2-Alkylated 1,3-dicarbonyl compounds react with the activated diene to produce substituted allenes in high yield. Phenylsulfonyl alkenyl substituted allenes were conveniently prepared by a similar protocol and were found to serve as substrates for intramolecular [2 + 2] cycloaddition chemistry.
• Intramolecular [4+4]-photocycloadditions of 2-pyrones: an efficient approach to cyclooctanoid construction
  作者：F. G. West、C. E. Chase、Atta M. Arif

  DOI：10.1021/jo00067a006

  日期：1993.7

  2-Pyrones 2 bearing pendant furans underwent efficient intramolecular crossed [4 + 4]-cycloaddition to give fused bicyclic cyclooctadienes 3 and 4 bridged by lactones and ethers, along with varying amounts of [2 + 2]-adducts 5.
• Elming, Acta Chemica Scandinavica (1947), 1956, vol. 10, p. 1664
  作者：Elming

  DOI：——

  日期：——
• Chemistry of 3,4-epoxy-2-methylene oxolanes: A new synthesis of furanes and dihydrofuranes
  作者：V. Dalla、P. Pale

  DOI：10.1016/0040-4039(96)00442-x

  日期：1996.4

  Dihydrofurans were obtained by selective 1,4-nucleophilic additions to 3,4-epoxy-2-methylene oxolanes(EMO). Aromatization gave the corresponding substituted furans. Copyright (C) 1996 Published by Elsevier Science Ltd