2,5-dihydro-4,5,5-trimethyl-2-oxo-5-furancarboxylic acid methyl ester | 73689-84-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 2,5-dihydro-4,5,5-trimethyl-2-oxo-5-furancarboxylic acid methyl ester
• 英文别名: α-methoxycarbonyl-β-methyl-γ,γ-dimethyl-Δ^α,β-butenolide；methyl 4,5,5-trimethyl-2-oxo-2,5-dihydrofuran-3-carboxylate；methyl 4,5,5′-trimethyl-2-oxo-2,5-dihydrofuran-3-carboxylate；2-methoxycarbonyl-3,4,4-trimethyl-2-buten-4-olide；4,5,5-trimethyl-2-oxo-2,5-dihydro-furan-3-carboxylic acid methyl ester；Methyl 4,5,5-trimethyl-2-oxofuran-3-carboxylate
• CAS: 73689-84-6
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: DHLBESNKEFUTAT-UHFFFAOYSA-N

物化性质

• 熔点：
  47-48 °C(Solv: hexane (110-54-3))
• 沸点：
  135-138 °C(Press: 2-3 Torr)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5-dihydro-4,5,5-trimethyl-2-oxo-5-furancarboxylic acid methyl ester 、 3-羟基-3-甲基-2-丁酮 在 potassium carbonate 作用下， 反应 7.0h， 以50%的产率得到2,2,3,6,6-pentamethyl-1,7-dioxaspiro<4,4>non-3-ene-8-one
  参考文献：
  名称：

  Synthesis of heterospirans containing a γ-lactone ring

  摘要：

  Reactions of alpha-ketols with diethyl malonate at the molar ratio 2:1 in the presence of K(2)CO(3) were investigated. The heterospiranes obtained contained a dihydrofuran and a gamma-lactone rings. The optimum conditions for the synthesis of heterospiranes were found by varying the ratio of the initial compounds: alpha-ketoalcohol (or 2-ethoxycarbonyl-, 2-methoxycarbonyl-, 2-cyano-3,4,4-trimethyl-2-buten-4-olides), diethyl malonate, K(2)CO(3), by varying the environment, and also the temperature and the time of the reaction.

  DOI：

  10.1134/s1070428008070221
• 作为产物：
  描述：

  methyl 5,5-dimethyl-2-oxo-2,5-dihydrofuran-3-carboxylate 以 甲醇 、 乙醚 为溶剂， 反应 0.17h， 生成 2,5-dihydro-4,5,5-trimethyl-2-oxo-5-furancarboxylic acid methyl ester
  参考文献：
  名称：

  Gulbrandsen, Trygve; Kolsaker, Per, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1980, vol. 34, # 10, p. 305 - 308

  摘要：

  DOI：

文献信息

• Development of a Cross‐Conjugated Vinylogous [4+2] Anionic Annulation and Application to the Total Synthesis of Natural Antibiotic (±)‐ABX
  作者：Jing‐Kai Huang、Kak‐Shan Shia

  DOI：10.1002/anie.201914657

  日期：2020.4.16

  vinylogous [4+2] anionic annulation has been newly developed, the cascade process of which has a high preference for regiochemical control and chemoselectivity, giving rise to exclusively Michael-type adducts in moderate to high yields (up to 94 %, 35 examples). By making use of this approach as a key operation, the first total synthesis of natural antibiotic ABX, in racemic form, has been successfully

  交叉共轭的乙烯基[4 + 2]阴离子环化技术已经得到了新的发展，其级联工艺对区域化学控制和化学选择性具有很高的偏爱，从而以中等至高的收率（高达94％的产率）产生了唯一的迈克尔型加合物。 （35个示例）。通过将该方法用作关键操作，已成功地以简明的7个步骤成功完成了外消旋形式的天然抗生素ABX的首次全合成，总收率约为20％。
• Stable aziridinium salts of oxalic and 2,5-dihydro-4,5,5-trimethyl-2-oxo-5-furancarboxylic acids
  作者：A. A. Avetisyan、V. V. Ovsepyan、R. G. Kostyanovskii

  DOI：10.1007/bf01167783

  日期：1983.1
• Tuning the solid-state emission of small push-pull dipolar dyes to the far-red through variation of the electron-acceptor group
  作者：Sébastien Redon、Gwenaëlle Eucat、Martin Ipuy、Erwann Jeanneau、Isabelle Gautier-Luneau、Alain Ibanez、Chantal Andraud、Yann Bretonnière

  DOI：10.1016/j.dyepig.2018.03.049

  日期：2018.9

  Series of solid-state emitters based on the D-pi-A dipolar structure and featuring various electron-donor and electron-acceptor groups were designed, and their spectroscopic properties studied. From weak emission in dilute solutions, intense emissions in aggregated state (ATE) and in the crystalline state were obtained. Analysis in light of crystal structures obtained by X-ray diffraction revealed specific crystal packing and presence of long chain of emitting aggregates. This simple molecular engineering around the D-pi-A dipolar structure provides easy access to a wide range of effective solid-state emitters allowing modulation of emission wavelengths up to the near infrared (lambda(em) reaching 735 and 768 nm for compound 2f and 3f bearing the strongest electron-withdrawing group).
• Phosphor- und schwefelsubstituierte allene - IV. Eine einfache synthese von 2[5H]furanonen und β-methylen-γ-butyrolactonen durch addition von malonsäureester an allensulfoxide
  作者：Hans-Josef Altenbach、Hartwig Soicke

  DOI：10.1016/s0040-4039(00)84312-9

  日期：1986.1
• GULBRANDSEN T.; KOLSAKER P., ACTA CHEM. SCAND., 1980, B 34, NO 4, 305-307
  作者：GULBRANDSEN T.、 KOLSAKER P.

  DOI：——

  日期：——