3-(acetoxymethyl)-6-<(1E)-7-<<(1,1-dimethylethyl)dimethylsilyl>oxy>heptenyl>-4-methoxy-2H-pyran-2-one | 218435-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-(acetoxymethyl)-6-<(1E)-7-<<(1,1-dimethylethyl)dimethylsilyl>oxy>heptenyl>-4-methoxy-2H-pyran-2-one
• 英文别名: [6-[(E)-7-[tert-butyl(dimethyl)silyl]oxyhept-1-enyl]-4-methoxy-2-oxopyran-3-yl]methyl acetate
• CAS: 218435-81-5
• 化学式: C₂₂H₃₆O₆Si
• 分子量: 424.61
• InChiKey: SQDXZJVDUUPVSG-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(acetoxymethyl)-6-<(1E)-7-<<(1,1-dimethylethyl)dimethylsilyl>oxy>heptenyl>-4-methoxy-2H-pyran-2-one 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 为溶剂， 反应 11.0h， 以91%的产率得到3-(acetoxymethyl)-6-<(1E)-7-hydroxy-1-heptenyl>-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 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以81%的产率得到3-(acetoxymethyl)-6-<(1E)-7-<<(1,1-dimethylethyl)dimethylsilyl>oxy>heptenyl>-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