methyl (4-hydroxy-5,5-dimethyltetrahydrofuran-2-ylidene)acetate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: methyl (4-hydroxy-5,5-dimethyltetrahydrofuran-2-ylidene)acetate
• 英文别名: methyl (2Z)-2-(4-hydroxy-5,5-dimethyloxolan-2-ylidene)acetate
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: AQMMFJMLWOZTGQ-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  dimethylvinyl ethynyl carbinol 在 四(甲基苯基膦)钯 硫酸 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 20.0 ℃ 、2.07 MPa 条件下， 反应 4.25h， 生成 methyl (4-hydroxy-5,5-dimethyltetrahydrofuran-2-ylidene)acetate
  参考文献：
  名称：

  Carbonylation of Alkynyl Epoxides:  Synthesis of 5-Hydroxy-2,3-dienoate Esters and 2,3-Dihydrofuran-3-ol Derivatives

  摘要：

  The carbonylation of alkynyl oxiranes catalyzed by (MePh2)(4)Pd in the presence of 20 atm of carbon monoxide in methanol gives methyl 5-hydroxy-2,3-pentadienoates in good yields. When the reaction is performed on alkynyl oxiranemethanol derivatives, 4,5-dihydrofuran-3-ol derivatives are obtained stereoselectively. These products arise from the spontaneous cyclization of a dihydroxyallenyl ester intermediate.

  DOI：

  10.1021/jo971303n

文献信息

• Carbonylation of Alkynyl Epoxides:  Synthesis of 5-Hydroxy-2,3-dienoate Esters and 2,3-Dihydrofuran-3-ol Derivatives
  作者：Marcelo E. Piotti、Howard Alper

  DOI：10.1021/jo971303n

  日期：1997.11.1

  The carbonylation of alkynyl oxiranes catalyzed by (MePh2)(4)Pd in the presence of 20 atm of carbon monoxide in methanol gives methyl 5-hydroxy-2,3-pentadienoates in good yields. When the reaction is performed on alkynyl oxiranemethanol derivatives, 4,5-dihydrofuran-3-ol derivatives are obtained stereoselectively. These products arise from the spontaneous cyclization of a dihydroxyallenyl ester intermediate.