methyl <2-(5-methylene)tetrahydrofuryliden>acetate | 146896-50-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: methyl <2-(5-methylene)tetrahydrofuryliden>acetate
• 英文别名: methyl 2-(5-methylideneoxolan-2-ylidene)acetate
• CAS: 146896-50-6
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: WCXBBELOGDOZGL-UHFFFAOYSA-N

物化性质

• 沸点：
  244.7±40.0 °C(predicted)
• 密度：
  1.09±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl <2-(5-methylene)tetrahydrofuryliden>acetate 在 Amberlist 作用下， 以 苯 为溶剂， 反应 3.0h， 以66%的产率得到2-<(carbomethoxy)methyl>-5-methylfuran
  参考文献：
  名称：

  Elimination reactions of terminal .beta.-oxy selenoxides. Synthesis of aryl and vinyl enol ethers and of furans, oxazoles, and thiazoles

  摘要：

  Elimination reactions of terminal selenoxides holding an alkoxy group in the beta position, RCH-(OR)CH2SeOPh, are usually difficult and can give rise to complex reaction mixtures. We report that these reactions take place more easily whenever the oxygen atom is linked to an unsaturated group (-CH=CHR, -Ar, -CR=O, -CH=NR). These selenoxides are easily available, and the elimination reaction was employed to effect useful syntheses of both open-chain and cyclic aryl and vinyl enol ethers. Moreover, by simple isomerization with acids or bases the cyclic derivatives can be transformed into the corresponding furans. The same procedure has been employed to synthesize substituted oxazoles and thiazoles also.

  DOI：

  10.1021/jo00058a011
• 作为产物：
  描述：

  [5-Phenylselanylmethyl-dihydro-furan-(2Z)-ylidene]-acetic acid methyl ester 在 双氧水 、 碳酸氢钠 作用下， 以 甲醇 、 苯 为溶剂， 反应 21.0h， 生成 methyl <2-(5-methylene)tetrahydrofuryliden>acetate
  参考文献：
  名称：

  Elimination reactions of terminal .beta.-oxy selenoxides. Synthesis of aryl and vinyl enol ethers and of furans, oxazoles, and thiazoles

  摘要：

  Elimination reactions of terminal selenoxides holding an alkoxy group in the beta position, RCH-(OR)CH2SeOPh, are usually difficult and can give rise to complex reaction mixtures. We report that these reactions take place more easily whenever the oxygen atom is linked to an unsaturated group (-CH=CHR, -Ar, -CR=O, -CH=NR). These selenoxides are easily available, and the elimination reaction was employed to effect useful syntheses of both open-chain and cyclic aryl and vinyl enol ethers. Moreover, by simple isomerization with acids or bases the cyclic derivatives can be transformed into the corresponding furans. The same procedure has been employed to synthesize substituted oxazoles and thiazoles also.

  DOI：

  10.1021/jo00058a011

文献信息

• 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。
• Elimination reactions of terminal .beta.-oxy selenoxides. Synthesis of aryl and vinyl enol ethers and of furans, oxazoles, and thiazoles
  作者：Marcello Tiecco、Lorenzo Testaferri、Marco Tingoli、Francesca Marini

  DOI：10.1021/jo00058a011

  日期：1993.3

  Elimination reactions of terminal selenoxides holding an alkoxy group in the beta position, RCH-(OR)CH2SeOPh, are usually difficult and can give rise to complex reaction mixtures. We report that these reactions take place more easily whenever the oxygen atom is linked to an unsaturated group (-CH=CHR, -Ar, -CR=O, -CH=NR). These selenoxides are easily available, and the elimination reaction was employed to effect useful syntheses of both open-chain and cyclic aryl and vinyl enol ethers. Moreover, by simple isomerization with acids or bases the cyclic derivatives can be transformed into the corresponding furans. The same procedure has been employed to synthesize substituted oxazoles and thiazoles also.