3-Ethynyl-α,α-dimethyl-2-oxiranemethanol | 197307-20-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Ethynyl-α,α-dimethyl-2-oxiranemethanol
• 英文别名: 2-(3-Ethynyloxiran-2-yl)propan-2-ol
• CAS: 197307-20-3
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: PFRJLRVKHUTGAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲醇 、 一氧化碳 、 3-Ethynyl-α,α-dimethyl-2-oxiranemethanol 在 四(甲基苯基膦)钯 作用下， 20.0 ℃ 、2.07 MPa 条件下， 反应 2.0h， 以91%的产率得到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
• 作为产物：
  描述：

  dimethylvinyl ethynyl carbinol 在 硫酸 、 间氯过氧苯甲酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 3-Ethynyl-α,α-dimethyl-2-oxiranemethanol
  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.