dimethyl 2-methylfuran-3,4-dicarboxylate | 6141-60-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃
• 英文名称: dimethyl 2-methylfuran-3,4-dicarboxylate
• 英文别名: 3,4-Di-methoxycarbonyl-2-methyl-furan；2-Methyl-3,4-furandicarboxylic acid dimethyl ester
• CAS: 6141-60-2
• 化学式: C₉H₁₀O₅
• 分子量: 198.175
• InChiKey: UWCACUCRHMWBPA-UHFFFAOYSA-N

物化性质

• 沸点：
  115-117 °C(Press: 5 Torr)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  dimethyl 2-methylfuran-3,4-dicarboxylate 以68%的产率得到
  参考文献：
  名称：

  SAIKACHI H.; KITAGAWA T., CHEM. AND PHARM. BULL. , 1977, 25, NO 4, 809-811

  摘要：

  DOI：
• 作为产物：
  描述：

  1-Methyl-7-oxa-bicyclo[2.2.1]hept-2-ene-2,3-dicarboxylic acid dimethyl ester 以87%的产率得到dimethyl 2-methylfuran-3,4-dicarboxylate
  参考文献：
  名称：

  Synthesis of Benzene Derivatives via Deoxygenation by Low Valent Titanium

  摘要：

  DOI：

  10.1055/s-1984-30976

文献信息

• Triflic Acid-Mediated Rearrangements of 3-Methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones: Synthesis of Methoxytropolones and Furans
  作者：Yvonne D. Williams、Christine Meck、Noushad Mohd、Ryan P. Murelli

  DOI：10.1021/jo401617r

  日期：2013.12.6

  because of their known biological activity and established value in the synthesis of α-hydroxytropolones. Upon treatment with triflic acid, a series of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones rearrange rapidly and cleanly to form methoxytropolones. Interestingly, bicycles that are derived from dimethyl acetylenedicarboxylate (R2 = R3 = CO2Me) instead form furans as the major product.

  甲氧基托酚酮是用于治疗开发的有用支架，因为其已知的生物活性和在 α-羟基托酚酮合成中的确定价值。用三氟甲磺酸处理后，一系列 3-甲氧基-8-氧杂二环[3.2.1]八-3,6-二烯-2-酮快速而干净地重排，形成甲氧基托酚酮。有趣的是，衍生自乙炔二甲酸二甲酯（R 2 = R 3 = CO 2 Me）的自行车反而形成呋喃作为主要产物。
• A Mild, Convenient and Efficient Single-Step Method for the Synthesis of Polysubstituted Furans via Ammonium Ylide Routes
  作者：Yongmin Liang、Mingjin Fan、Lina Guo、Xueyuan Liu、Weimin Liu

  DOI：10.1055/s-2004-834944

  日期：——

  A new and convenient cyclization method for the synthesis of polysubstituted furans in a single-step via ammonium ylide routes was reported. In this process, dimethyl acetylenedicarboxylate reacted with ammonium ylide to produce polysubstituted furan in the presence of anhydrous K2CO3 at room temperature. It is very economical, environmentally friendly and very easy to carry out.

  报道了一种通过铵叶立德路线一步合成多取代呋喃的新型便捷环化方法。在这个过程中，乙炔二甲酸二甲酯在室温下，在无水 K2CO3 存在下，与内立铵铵反应生成多取代呋喃。它非常经济、环保且非常易于实施。
• 无碱、无溶剂条件通过Feist-Benary反应制备 多取代呋喃的方法
  申请人：重庆医科大学

  公开号：CN106243072B

  公开（公告）日：2018-09-28

  本发明提供一种制备多取代呋喃的方法，即在无碱、无溶剂条件下，α‑卤代酮与β‑二羰基化合物发生反应得到多取代呋喃化合物。本发明所述的多取代呋喃化合物的制备方法，原料易得，成本低廉，反应条件温和，操作简单易控，副反应较少，后处理简单，产品收率较高，无需任何催化剂和溶剂，大大节约了生产成本，具有较好的环保效益和经济效益，适宜于工业化大生产。
• Studies dealing with the excited-state behavior of substituted 8-oxabicyclo[3.2.1]oct-6-en-2-ones
  作者：Albert Padwa、Lin Zhi、Glen E. Fryxell

  DOI：10.1021/jo00003a032

  日期：1991.2

  A series of 8-oxabicyclo [3.2.1]oct-6-en-2-ones was prepared by the rhodium(II)-catalyzed cyclization-cycloaddition reaction of alpha-diazopentanedione with various alkynes. The photochemical behavior of these oxabicyclic enones was investigated. Both direct and sensitized photolysis cleanly results in a 1,3-acyl shift. A slower, secondary photoprocess involving intramolecular hydrogen atom transfer and intramolecular cycloaddition of the resulting ketene was also uncovered. The photobehavior of the closely related 9-oxabenzocycloheptene system was also examined. The initially formed 1,3-sigmatropic rearranged product was found to undergo a novel 1,4-methoxyl migration on extended photolysis. The photochemistry of the homologous 7-oxabicyclo[2.2.1]hepten-2-one was studied. The results obtained can be interpreted in terms of an initial Norrish type I cleavage. The resulting diradical either couples to give the 1,3-acyl shift product or undergoes bond fragmentation, giving products derived from a stepwise retro-Diels-Alder reaction.
• MEDVEDSKAYA L. B.; KONDRATEVA G. YA.; BYKANOVA N. V., IZV. AN CCCP. CEP. XIM., 1979, HO 7, 1613-1615
  作者：MEDVEDSKAYA L. B.、 KONDRATEVA G. YA.、 BYKANOVA N. V.

  DOI：——

  日期：——