2,4,4-Trimethoxy-7-methyl-2,3-dihydrochromen-3-ol | 206984-74-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2,4,4-Trimethoxy-7-methyl-2,3-dihydrochromen-3-ol
• CAS: 206984-74-9
• 化学式: C₁₃H₁₈O₅
• 分子量: 254.283
• InChiKey: VLYCATZXFZKIOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4,4-Trimethoxy-7-methyl-2,3-dihydrochromen-3-ol 在 盐酸 、 potassium carbonate 作用下， 以 丙酮 、 苯 为溶剂， 反应 35.0h， 生成 cis-1,2,2a,7c-tetrahydro-5-methyl-7c-oxeto-9H-benzo[b]cyclobuta[e]pyran-7b-ol
  参考文献：
  名称：

  Convenient Synthesis of an A-Ring Aromatic Trichothecene Analog

  摘要：

  A short and convenient route to the synthesis of A-ring aromatic trichothecene analogue 2 is described, employing a cyclobutyl carbinol rearrangement as the key step. Cycloaddition of ethylene to the methoxychromone 6 furnished the oxetanol 7 along with some cycloadduct 8, the latter arising from cleavage of 7. Lithium aluminum hydride reduction of 7 to the diol 9 followed by acid-catalyzed rearrangement afforded the benzooxabicyclo[3.2.1]octanone 10, through exclusive external bond migration. Interaction of 10 with dimethyloxosulfonium methylide furnished the desired anti-epoxide 2, whereas dimethyl sulfonium methylide yielded the syn-epoxide 12. Reduction of these epoxides provided the alcohols 13 and 14, respectively. Addition of methylmagnesium iodide to ketone 10 furnished exclusively alcohol 14, supporting the stereoassignments.

  DOI：

  10.1021/jo971970g
• 作为产物：
  描述：

  甲醇 、 7-methyl-4H-benzopyran-4-one 在 碘苯二乙酸 、 hydroxide 作用下， 生成 2,4,4-Trimethoxy-7-methyl-2,3-dihydrochromen-3-ol
  参考文献：
  名称：

  Convenient Synthesis of an A-Ring Aromatic Trichothecene Analog

  摘要：

  A short and convenient route to the synthesis of A-ring aromatic trichothecene analogue 2 is described, employing a cyclobutyl carbinol rearrangement as the key step. Cycloaddition of ethylene to the methoxychromone 6 furnished the oxetanol 7 along with some cycloadduct 8, the latter arising from cleavage of 7. Lithium aluminum hydride reduction of 7 to the diol 9 followed by acid-catalyzed rearrangement afforded the benzooxabicyclo[3.2.1]octanone 10, through exclusive external bond migration. Interaction of 10 with dimethyloxosulfonium methylide furnished the desired anti-epoxide 2, whereas dimethyl sulfonium methylide yielded the syn-epoxide 12. Reduction of these epoxides provided the alcohols 13 and 14, respectively. Addition of methylmagnesium iodide to ketone 10 furnished exclusively alcohol 14, supporting the stereoassignments.

  DOI：

  10.1021/jo971970g

文献信息

• Convenient Synthesis of an A-Ring Aromatic Trichothecene Analog
  作者：Jayati Mal、Ramanathapuram V. Venkateswaran

  DOI：10.1021/jo971970g

  日期：1998.6.1

  A short and convenient route to the synthesis of A-ring aromatic trichothecene analogue 2 is described, employing a cyclobutyl carbinol rearrangement as the key step. Cycloaddition of ethylene to the methoxychromone 6 furnished the oxetanol 7 along with some cycloadduct 8, the latter arising from cleavage of 7. Lithium aluminum hydride reduction of 7 to the diol 9 followed by acid-catalyzed rearrangement afforded the benzooxabicyclo[3.2.1]octanone 10, through exclusive external bond migration. Interaction of 10 with dimethyloxosulfonium methylide furnished the desired anti-epoxide 2, whereas dimethyl sulfonium methylide yielded the syn-epoxide 12. Reduction of these epoxides provided the alcohols 13 and 14, respectively. Addition of methylmagnesium iodide to ketone 10 furnished exclusively alcohol 14, supporting the stereoassignments.