2H-Pyran-5-carboxylic acid, 3-acetyl-4-hydroxy-6-methyl-2-oxo-, methylester | 154368-85-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2H-Pyran-5-carboxylic acid, 3-acetyl-4-hydroxy-6-methyl-2-oxo-, methylester
• 英文别名: 5-Acetyl-4-hydroxy-2-methyl-6-oxo-6H-pyran-3-carboxylic acid methyl ester
• CAS: 154368-85-1
• 化学式: C₁₀H₁₀O₆
• 分子量: 226.186
• InChiKey: CUKXAHUDXSWPDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.64
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  93.81
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2H-Pyran-5-carboxylic acid, 3-acetyl-4-hydroxy-6-methyl-2-oxo-, methylester 在 甲醇 、 dimethyl sulfide borane 作用下， 生成 5-Ethyl-4-hydroxy-2-methyl-6-oxo-6H-pyran-3-carboxylic acid methyl ester 、 (2S,4R)-2-(4-Hydroxy-5-methoxycarbonyl-6-methyl-2-oxo-2H-pyran-3-yl)-4,7-dimethyl-5-oxo-3,4-dihydro-2H,5H-pyrano[4,3-b]pyran-8-carboxylic acid methyl ester
  参考文献：
  名称：

  Reduction of a-Pyrone Derivatives with Borane-Methyl Sulfide Complex

  摘要：

  Selective reduction of the 5-carbomethoxy- and the 5-carbethoxy-4-hydroxy-2H-pyran-2-one derivatives (5a approximately 11, 19) to yield the 5-hydroxymethyl derivatives (12 approximately 18) was accomplished using 1.1 mol equivalent of borane-methyl sulfide complex. Additionally, reduction of the 3-acetyl-4-hydroxy-2H-pyran-2-one derivatives (23, 26 and 29) with borane-methyl sulfide complex afforded the binary condensed pyrone derivatives (25, 28 and 3 1) in good yields.

  DOI：

  10.3987/com-93-6509
• 作为产物：
  描述：

  1,1-二氯甲醚 、 5-carbomethoxy-4-hydroxy-6-methyl-2H-pyran-2-one 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以89%的产率得到2H-Pyran-5-carboxylic acid, 3-acetyl-4-hydroxy-6-methyl-2-oxo-, methylester
  参考文献：
  名称：

  Total Synthesis of Islandic Acid I Methyl Ester, Rosellisin and Rosellisin Aldehyde

  摘要：

  Total synthesis of islandic acid I methyl ester (2), rosellisin (3) and rosellisin aldehyde (4) has been accomplished starting from 4-hydroxy-5-hydroxymethyl-6-methyl-2H-pyran-2-one (9a) via formylation of 9a with dichloromethyl methyl ether and titanium tetrachloride as a key step.

  DOI：

  10.3987/com-93-6568