ethyl 2-methyl-5-methylene-4,5-dihydrofuran-3-carboxylate | 122132-58-5

• 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: ethyl 2-methyl-5-methylene-4,5-dihydrofuran-3-carboxylate
• 英文别名: 3-ethoxycarbonyl-2-methyl-5-methylene-4,5-dihydrofuran；3-Furancarboxylic acid, 4,5-dihydro-2-methyl-5-methylene-, ethyl ester；ethyl 5-methyl-2-methylidene-3H-furan-4-carboxylate
• CAS: 122132-58-5
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: FNJJTCRDPIXDRK-UHFFFAOYSA-N

物化性质

• 沸点：
  242.0±40.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-methyl-5-methylene-4,5-dihydrofuran-3-carboxylate 在 偶氮二异丁腈 、 氧气 、 silica gel 作用下， 以 苯 为溶剂， 反应 6.0h， 生成 乙基5-甲酰基-2-甲基呋喃-3-羧酸酯
  参考文献：
  名称：

  Antonioletti, Roberto; Bonadies, Francesco; Floro, Cristina, Gazzetta Chimica Italiana, 1990, vol. 120, # 7, p. 471 - 472

  摘要：

  DOI：
• 作为产物：
  描述：

  2-乙酰基-4-戊酸乙酯 在 碘 、 sodium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 ethyl 2-methyl-5-methylene-4,5-dihydrofuran-3-carboxylate
  参考文献：
  名称：

  A convenient approach to furan derivatives by I2-induced cyclisation of 2-alkenyl substituted 1,3-dicarbonyl compounds

  摘要：

  DOI：

  10.1016/s0040-4039(00)80660-7

文献信息

• Synthesis of spirocyclic acetals by manganic acetate promoted additions to exocyclic enol ethers
  作者：John M. Mellor、Shahid Mohammed

  DOI：10.1016/s0040-4020(01)87231-8

  日期：1993.8

  Reaction of β-ketoesters and β-dicarbonyl compounds with manganic acetate in acetic acid gives intermediates, which add to exocyclic enol ethers to afford a variety of interesting spirocyclic acetals. As the exocyclic enol ethers are shown to be readily accessible, the results constitute a useful route based on radical chemistry to the synthesis of unsaturated spiroacetals.

  β-酮酸酯和β-二羰基化合物与乙酸锰在乙酸中的反应生成中间体，将其加至环外烯醇醚中可制得各种有趣的螺环缩醛。由于显示出环外烯醇醚易于获得，因此该结果构成了基于自由基化学方法合成不饱和螺缩醛的有用途径。
• Chemical, photochemical and enzymatic approach to furylhydroperoxides
  作者：Arrigo Scettri、Francesco Bonadies、Alessandra Lattanzi、Laura Palombi、Silvia Pesci

  DOI：10.1016/s0040-4020(97)10135-1

  日期：1997.12

  Furylhydroperoxides are accessible by three different methodologies. In the enzymatic approach, lypoxygenase is employed on non lipid-like substrates. Transition metal catalyzed epoxidation of allylic alcohols is strongly dependent on the structure of the involved hydroperoxide.

  呋喃基氢过氧化物可通过三种不同的方法获得。在酶促方法中，在非脂质样底物上使用了加氧合酶。过渡金属催化的烯丙基醇的环氧化强烈依赖于所涉及的氢过氧化物的结构。
• CuI-catalyzed intramolecular O-vinylation of carbonyl compounds
  作者：Yewen Fang、Chaozhong Li

  DOI：10.1039/b505006e

  日期：——

  The first copper-catalyzed intramolecular O-vinylation of carbonyl compounds with vinyl bromides was reported, among which the efficient formation of 5-, 6- and even 7-membered cyclic alkenyl ethers was achieved with β-ketoesters as nucleophiles.

  首次报道了铜催化的羰基化合物与乙烯基溴化物之间的分子内O-乙烯化反应，其中使用β-酮酯作为亲核试剂，成功合成了5、6甚至7元环烯基醚。
• Synthesis of oxygen spirocycles by manganic acetate promoted additions to exocyclic enol ether derivatives
  作者：John M. Mellor、Shahid Mohammed

  DOI：10.1016/0040-4039(91)85053-8

  日期：1991.11

  Oxidative addition, promoted by manganic acetate, of β-dicarbonyl compounds to enol lactones and related enol derivatives having an exocyclic double bond affords spirocyclic products, and addition to endocyclic enol ethers gives fused acetals and ketals.

  由乙酸锰促进的β-二羰基化合物氧化加成至烯醇内酯和具有环外双键的相关烯醇衍生物可得到螺环产物，而加到环内烯醇醚上则可得到缩合缩醛和缩酮。
• Mo(CO)6/TBHP catalyzed autoxidation of 5-alkylidene-4,5-dihydrofurans
  作者：Alessandra Lattanzi、Patrizia Iannece、Arrigo Scettri

  DOI：10.1016/s0040-4039(99)00564-x

  日期：1999.5

  , well known to epoxidize olefins, was shown to be a mild and very efficient system for the autoxidation of 5-alkylidene-4,5-dihydrofurans. High yields of primary, secondary and tertiary furyl hydroperoxides have been achieved employing catalytic amount of Mo(CO)6. A radical mechanism is in agreement with the experimental data.

  众所周知，环氧化烯烃是一种对5-亚烷基-4,5-二氢呋喃的自氧化的温和且非常有效的系统。使用催化量的Mo（CO）6已实现了高产率的伯，仲和叔呋喃氢过氧化物。根本机理与实验数据一致。

表征谱图