α,α-Dimethoxy-γ-butyrolactone | 165127-42-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α,α-Dimethoxy-γ-butyrolactone
• 英文别名: 3,3-Dimethoxyoxolan-2-one
• CAS: 165127-42-4
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: TUQWYRRZBPODHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲基锂 、 α,α-Dimethoxy-γ-butyrolactone 在 氘代氯仿 、 potassium carbonate 作用下， 生成 2-Deuteroxy-2-D3-methyl-3,3-dimethoxytetrahydrofuran
  参考文献：
  名称：

  Synthesis of Laurencione, a Labile Dihydro-3(2H)-furanone Derivative from the Red Alga Laurencia spectabilis

  摘要：

  The first total synthesis of laurencione, a naturally occurring dihydro-3(2H-furanone derivative isolated from the red alga Laurencia spectabilis, is described. The synthesis is comprised (1) of conversion of gamma-butyrolactone into alpha,alpha-dimethoxy-gamma-butyrolactone, (2) addition of methyllithium across the lactone carbonyl, and (3) acid hydrolysis of the acetal moiety. An alternative synthesis consists of the acid-catalyzed conversion of 3,3-dimethoxy-2-hydroxy-2-methyltetrahydrofuran into laurencione methyl ether and subsequent acid-catalyzed hydrolysis. In addition, a convenient synthesis of the coffee and caramel flavor component 2-methyl-3(2H)-furanone has been developed by acid-catalyzed rearrangement of 2-methoxy-2-methyltetrahydrofuran-3-one.

  DOI：

  10.1021/jo00121a051
• 作为产物：
  描述：

  甲醇 、 α-Chloro-α-(ethylthio)-γ-butyrolactone 在 mercury(II) diacetate 作用下， 以 四氯化碳 为溶剂， 反应 16.0h， 生成 α,α-Dimethoxy-γ-butyrolactone
  参考文献：
  名称：

  Synthesis of Laurencione, a Labile Dihydro-3(2H)-furanone Derivative from the Red Alga Laurencia spectabilis

  摘要：

  The first total synthesis of laurencione, a naturally occurring dihydro-3(2H-furanone derivative isolated from the red alga Laurencia spectabilis, is described. The synthesis is comprised (1) of conversion of gamma-butyrolactone into alpha,alpha-dimethoxy-gamma-butyrolactone, (2) addition of methyllithium across the lactone carbonyl, and (3) acid hydrolysis of the acetal moiety. An alternative synthesis consists of the acid-catalyzed conversion of 3,3-dimethoxy-2-hydroxy-2-methyltetrahydrofuran into laurencione methyl ether and subsequent acid-catalyzed hydrolysis. In addition, a convenient synthesis of the coffee and caramel flavor component 2-methyl-3(2H)-furanone has been developed by acid-catalyzed rearrangement of 2-methoxy-2-methyltetrahydrofuran-3-one.

  DOI：

  10.1021/jo00121a051

文献信息

• Synthesis of Laurencione, a Labile Dihydro-3(2H)-furanone Derivative from the Red Alga Laurencia spectabilis
  作者：Norbert De Kimpe、Angelina Georgieva、Marc Boeykens、Laszlo Lazar

  DOI：10.1021/jo00121a051

  日期：1995.8

  The first total synthesis of laurencione, a naturally occurring dihydro-3(2H-furanone derivative isolated from the red alga Laurencia spectabilis, is described. The synthesis is comprised (1) of conversion of gamma-butyrolactone into alpha,alpha-dimethoxy-gamma-butyrolactone, (2) addition of methyllithium across the lactone carbonyl, and (3) acid hydrolysis of the acetal moiety. An alternative synthesis consists of the acid-catalyzed conversion of 3,3-dimethoxy-2-hydroxy-2-methyltetrahydrofuran into laurencione methyl ether and subsequent acid-catalyzed hydrolysis. In addition, a convenient synthesis of the coffee and caramel flavor component 2-methyl-3(2H)-furanone has been developed by acid-catalyzed rearrangement of 2-methoxy-2-methyltetrahydrofuran-3-one.