4-methoxy-3,5,5-trimethyl-2(5H)-furanone

• 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: 4-methoxy-3,5,5-trimethyl-2(5H)-furanone
• 英文别名: 4-Methoxy-3,5,5-trimethylfuran-2-one
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: FQPAUADCVYPPSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  一氧化碳 、 3-甲氧基-2-甲基-戊-3,4-二烯-2-醇 在 十二羰基三钌 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 100.0 ℃ 、1.01 MPa 条件下， 反应 8.0h， 以95%的产率得到4-methoxy-3,5,5-trimethyl-2(5H)-furanone
  参考文献：
  名称：

  Ruthenium-Catalyzed Cyclocarbonylation of Allenyl Alcohols and Amines:  Selective Synthesis of Lactones and Lactams

  摘要：

  Allenyl alcohols such as 4-hydroxybuta-1,2-dienes and 5-hydroxypenta-1,2-dienes having a variety of substituents undergo cyclocarbonylation in the presence of a ruthenium catalyst under mild conditions selectively to give five- and six-membered lactones in a high yield with 100% atom economy. 5-Aminopenta-1,2-dines are also cyclocarbonylated to give gamma-lactams. A possible carbonylation mechanism involving a ruthenium cluster intermediate is proposed on the basis of experimental results.

  DOI：

  10.1021/jo0350615

文献信息

• Ruthenium-Catalyzed Cyclic Carbonylation of Allenyl Alcohols. Selective Synthesis of γ- and δ-Lactones
  作者：Eiji Yoneda、Takayuki Kaneko、Shi-Wei Zhang、Kiyotaka Onitsuka、Shigetoshi Takahashi

  DOI：10.1021/ol990377d

  日期：2000.2.1

  [GRAPHICS]Ruthenium complex catalyzed carbonylation of allenyl alcohols quantitatively gave cyclic carbonyl compounds, gamma- and delta-lactones, in which the hydroxy group of allenyl alcohols participated in the cyclization, A wide variety of allenyl alcohols, such as mono, di-, and trisubstituted alcohols, can be used in this reaction to produce 3- and 4-substituted gamma-lactones. Similarly, the cyclic carbonylation of 3,4-pentadien-1-ol 10a and 2-methyl-4,5-hexadien-2-ol 11a gave delta-lactones, 5,6-dihydro-3-methyl-2H-pyran-2-one 10b, and 5,6-dihydro-6,6-dimethyl-3-methyl-2H-pyran-2-one 11b, respectively, in a quantitative yield.
• Ruthenium-Catalyzed Cyclocarbonylation of Allenyl Alcohols and Amines:  Selective Synthesis of Lactones and Lactams
  作者：Eiji Yoneda、Shi-Wei Zhang、Da-Yang Zhou、Kiyotaka Onitsuka、Shigetoshi Takahashi

  DOI：10.1021/jo0350615

  日期：2003.10.1

  Allenyl alcohols such as 4-hydroxybuta-1,2-dienes and 5-hydroxypenta-1,2-dienes having a variety of substituents undergo cyclocarbonylation in the presence of a ruthenium catalyst under mild conditions selectively to give five- and six-membered lactones in a high yield with 100% atom economy. 5-Aminopenta-1,2-dines are also cyclocarbonylated to give gamma-lactams. A possible carbonylation mechanism involving a ruthenium cluster intermediate is proposed on the basis of experimental results.