3-(acetoxymethyl)-6-<(1E)-6-formyl-1-hexenyl>-4-methoxy-2H-pyran-2-one | 218435-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-(acetoxymethyl)-6-<(1E)-6-formyl-1-hexenyl>-4-methoxy-2H-pyran-2-one
• 英文别名: [4-methoxy-2-oxo-6-[(E)-7-oxohept-1-enyl]pyran-3-yl]methyl acetate
• CAS: 218435-83-7
• 化学式: C₁₆H₂₀O₆
• 分子量: 308.331
• InChiKey: IYNBRWUVMKINED-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  碘仿 、 3-(acetoxymethyl)-6-<(1E)-6-formyl-1-hexenyl>-4-methoxy-2H-pyran-2-one 在 chromium dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 3-(acetoxymethyl)-6-<(1E,7Z)-8-iodo-1,7-octadieyl>-4-methoxy-2H-pyran-2-one 、 3-(acetoxymethyl)-6-<(1E,7E)-8-iodo-1,7-octadieyl>-4-methoxy-2H-pyran-2-one
  参考文献：
  名称：

  Total Synthesis of (−)-Solanapyrone A via Enzymatic Diels−Alder Reaction of Prosolanapyrone

  摘要：

  The syntheses of prosolanapyrones I (6) and II (7) via the aldol reactions of pyrone and dienal segments have been achieved in five steps in 31% overall yield for 6 and seven steps in 5% overall yield for 7. An improved synthetic route starting from vinylpyrone 27 provided 7 in 11 steps in 12% overall yield. The enzymatic Diels-Alder reaction of 7 affords (-)-solanapyrone A (1) with high enantioselectivity and with good exo-selectivity, which is difficult to attain by chemical methods. In addition, a crude enzyme preparation from Alternaria solani has been used to perform a kinetic resolution of(+/-)-3.

  DOI：

  10.1021/jo980743r
• 作为产物：
  描述：

  Acetic acid 6-[2-acetoxy-7-(tert-butyl-dimethyl-silanyloxy)-heptyl]-4-methoxy-2-oxo-2H-pyran-3-ylmethyl ester 在 4-甲基苯磺酸吡啶 、 戴斯-马丁氧化剂 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 12.67h， 生成 3-(acetoxymethyl)-6-<(1E)-6-formyl-1-hexenyl>-4-methoxy-2H-pyran-2-one
  参考文献：
  名称：

  Total Synthesis of (−)-Solanapyrone A via Enzymatic Diels−Alder Reaction of Prosolanapyrone

  摘要：

  The syntheses of prosolanapyrones I (6) and II (7) via the aldol reactions of pyrone and dienal segments have been achieved in five steps in 31% overall yield for 6 and seven steps in 5% overall yield for 7. An improved synthetic route starting from vinylpyrone 27 provided 7 in 11 steps in 12% overall yield. The enzymatic Diels-Alder reaction of 7 affords (-)-solanapyrone A (1) with high enantioselectivity and with good exo-selectivity, which is difficult to attain by chemical methods. In addition, a crude enzyme preparation from Alternaria solani has been used to perform a kinetic resolution of(+/-)-3.

  DOI：

  10.1021/jo980743r