2-甲基-4,5-二氢呋喃-3-羧酸甲酯 | 32595-98-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 中文名称: 2-甲基-4,5-二氢呋喃-3-羧酸甲酯
• 英文名称: 4,5-Dihydro-2-methyl-3-furancarbonsaeure-methylester
• 英文别名: Methyl 4,5-Dihydro-2-methylfuran-3-carboxylate；methyl 2-methyl-4,5-dihydrofuran-3-carboxylate；4-Carbomethoxy-5-methyl-2,3-dihydrofuran；2-methyl-4,5-dihydro-furan-3-carboxylic acid methyl ester；2-Methyl-4,5-dihydro-furan-3-carbonsaeure-methylester；2-Methyl-3-methoxycarbonyl-4.5-dihydrofuran；methyl 5-methyl-2,3-dihydrofuran-4-carboxylate
• CAS: 32595-98-5
• 化学式: C₇H₁₀O₃
• mdl: MFCD09032500
• 分子量: 142.155
• InChiKey: IAHJHKXRMKTCJK-UHFFFAOYSA-N

物化性质

• 熔点：
  28-29 °C
• 沸点：
  78-84 °C(Press: 15 Torr)
• 密度：
  1.122±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932190090
• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  2-甲基-4,5-二氢呋喃-3-羧酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.33h， 生成 3-hydroxymethyl-2-methyl-4,5-dihydrofuran
  参考文献：
  名称：

  木酮基A，B，C，D和G类似物的合成

  摘要：

  由3-羟甲基-2-甲基-4，5-二氢呋喃和一系列相应的酚以明显直接的方式制备了一系列天然产物木酮缩醛A，B，C，D和G的脱甲基类似物。这些合成的关键步骤是三氟化硼二乙基醚化物促进的亲电子芳族取代反应。在合成木酮缩醛A的类似物的情况下，发现该方法是高效的（产率高达93％）。考虑到该转化至少涉及六个单独的反应，这些反应产物的最佳分离产率是显着的。而且，这些合成研究为木酮缩醛天然产物的可能的生物起源提供了重要的见识。

  DOI：

  10.1021/jo052371+
• 作为产物：
  描述：

  methyl 2-methylchromone-3-carboxylate 在 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 72.0h， 生成 2-甲基-4,5-二氢呋喃-3-羧酸甲酯
  参考文献：
  名称：

  Heteroannulation of 4-oxo-4H-1-benzopyrans (chromones) via the conjugate addition of haloalkanols in the presence of base

  摘要：

  Chromones (4-oxo-4H-1-benzopyrans) bearing electron-withdrawing substituents at C-3 react with 2-haloethanols and potassium carbonate in acetone to produce tetrahydrofuro[2,3-b][1]benzopyran-4-ones, the heteroannulation proceeding via the conjugate addition of the haloethanol to the chromone, followed by intramolecular alkylation. Under the conditions of the reaction, the products derived from chromone-3-carbaldehydes undergo in situ deformylation.

  DOI：

  10.1016/s0040-4020(01)80889-9

文献信息

• Synthesis and reactions of simple 3(2H)-furanones
  作者：Amos B. Smith、Patricia A. Levenberg、Paula J. Jerris、Robert M. Scarborough、Peter M. Wovkulich

  DOI：10.1021/ja00396a034

  日期：1981.3
• Dye-sensitized photooxygenation of 2,3-dihydrofurans: competing [2 + 2] cycloadditions and ene reactions of singlet oxygen with a rigid cyclic enol ether system
  作者：Klaus Gollnick、Karen Knutzen-Mies

  DOI：10.1021/jo00012a040

  日期：1991.6

  Singlet oxygen reacts with 2,3-dihydrofuran (1), 5-methyl- (7), 4,5-dimethyl- (13), and 4-carbomethoxy-5-methyl-2,3-dihydrofuran (20), 5,6-dimethyl-3,4-dihydro-2H-pyran (26), and 3-methoxy-2-methyl-2-butene (32) in nonpolar and polar aprotic solvents to yield dioxetanes and allylic hydroperoxides, except 32, which gives only allylic hydroperoxides. The dioxetanes were isolated, but decompose slowly with weak chemiluminescence at room temperature to yield the corresponding dicarbonyl compounds. The allylic hydroperoxides produced by the cyclic enol ethers could not be isolated or separated by high vacuum distillation or by chromatography; the endocyclic allylic hydroperoxides arising from the dihydrofurans eliminate H2O2 to yield the corresponding furans while the exocyclic allylic hydroperoxides give unknown products. Allylic hydroperoxides 28 and 29 and the dioxetane 27 obtained from 26 yield the same dicarbonyl compound 31. The proportion of dioxetanes to allylic hydroperoxides depends on ring size and substitution of the enol ethers and on solvent polarity. Smaller ring size, greater electron-donor substitution, and solvent polarity favor the formation of dioxetanes at the expense of allylic hydroperoxides. It is noteworthy that enol ether 20, an alpha,beta-unsaturated ester, forms appreciable amounts of a dioxetane in polar solvents (44% in acetonitrile). Kinetic results show that the rate and product distribution of the ene reaction are independent of solvent polarity, whereas the rate of dioxetane formation increases with solvent polarity. It is suggested that [2 + 2] cycloadditions and ene reactions occur via different transition states and intermediates, zwitterions and perepoxides, respectively. Furthermore, the remarkable propensity to dioxetane formation of dihydrofurans compared to that of dihydropyrans and the other enol ethers seems to be due to the rigidity of the five-membered ring in the transition state and intermediate zwitterion.
• Korte; Machleidt, Chemische Berichte, 1957, vol. 90, p. 2137,2146
  作者：Korte、Machleidt

  DOI：——

  日期：——
• Staehle, Helmut; Koeppe, Herbert; Daniel, Helmut, Chemische Berichte, 1980, vol. 113, # 9, p. 2841 - 2851
  作者：Staehle, Helmut、Koeppe, Herbert、Daniel, Helmut、Pook, Karl-Heinz、Foerster, Hans-Joachim、et al.

  DOI：——

  日期：——
• STAEHLE H.; KOEPPE H.; DANIEL H.; POOK K.-H.; FOERSTER H.-J.; HECHT H.-J.+, CHEM. BER., 1980, 113, NO 9, 2841-2851
  作者：STAEHLE H.、 KOEPPE H.、 DANIEL H.、 POOK K.-H.、 FOERSTER H.-J.、 HECHT H.-J.+

  DOI：——

  日期：——