6-<2-hydroxy-7-<<(1,1-dimethylethyl)dimethylsilyl>oxy>heptyl>-4-methoxy-3-vinyl-2H-pyran-2-one | 218435-78-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-<2-hydroxy-7-<<(1,1-dimethylethyl)dimethylsilyl>oxy>heptyl>-4-methoxy-3-vinyl-2H-pyran-2-one
• 英文别名: 6-[7-[Tert-butyl(dimethyl)silyl]oxy-2-hydroxyheptyl]-3-ethenyl-4-methoxypyran-2-one
• CAS: 218435-78-0
• 化学式: C₂₁H₃₆O₅Si
• 分子量: 396.599
• InChiKey: IJBIWYKUJDCZHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-<2-hydroxy-7-<<(1,1-dimethylethyl)dimethylsilyl>oxy>heptyl>-4-methoxy-3-vinyl-2H-pyran-2-one 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 potassium osmate(VI) 、 sodium periodate 、 N-甲基吲哚酮 、 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 17.67h， 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
• 作为产物：
  描述：

  6-[(tert-butyldimethylsilyl)oxy]hexanal 、 4-methoxy-6-methyl-3-vinyl-2-pyrone 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以85%的产率得到6-<2-hydroxy-7-<<(1,1-dimethylethyl)dimethylsilyl>oxy>heptyl>-4-methoxy-3-vinyl-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

文献信息

• Total Synthesis of (−)-Solanapyrone A via Enzymatic Diels−Alder Reaction of Prosolanapyrone
  作者：Hideaki Oikawa、Tomonori Kobayashi、Kinya Katayama、Yuichi Suzuki、Akitami Ichihara

  DOI：10.1021/jo980743r

  日期：1998.11.1

  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.