(1'R*,3'R*)-methyl [1'-hydroxy-5',10'-dioxo-3',4',5',10'-tetrahydro-1'H-naphtho[2,3-c]pyran-3'-yl]acetate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异色满醌
• 英文名称: (1'R*,3'R*)-methyl [1'-hydroxy-5',10'-dioxo-3',4',5',10'-tetrahydro-1'H-naphtho[2,3-c]pyran-3'-yl]acetate
• 英文别名: methyl 2-[(1R,3R)-1-hydroxy-5,10-dioxo-3,4-dihydro-1H-benzo[g]isochromen-3-yl]acetate
• 化学式: C₁₆H₁₄O₆
• 分子量: 302.284
• InChiKey: UZSWBHQFVSBOST-VPTHRUTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-丁烯酸甲酯 在 锂硼氢 、 ammonium cerium(IV) nitrate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 1.33h， 生成 (1'R*,3'R*)-methyl [1'-hydroxy-5',10'-dioxo-3',4',5',10'-tetrahydro-1'H-naphtho[2,3-c]pyran-3'-yl]acetate
  参考文献：
  名称：

  摘要：

  The Diels Alder addition of naphthoquinone (2a) to 1-trimethylsilyloxybuta-1,3-diene (3) afforded a 1.4 : 1 ratio of Diels Alder adducts (5a) and (6a) which were easily separated by flash chromatography. Individual treatment of adducts (5a) and (6a) with tin( IV) chloride afforded dihydrofuran (11a) as an inseparable 1 : 1 mixture of diastereomers. Diels Alder addition of naphthoquinones (2a) and (2b) to 1-methoxy-1-trimethylsilyloxybuta-1,3-diene (4) followed by treatment with tin( IV) chloride afforded dihydrofurans (12a) and (12b) respectively, both as inseparable 1 : 1 mixtures of C2 epimers. Removal of the pantolactone auxiliary from dihydrofuran (12a) was achieved by using lithium borohydride, affording aldehyde (13) which underwent oxidative rearrangement by using ceric ammonium nitrate to pyranonaphthoquinone (14). The inability to separate the individual C2 epimers of dihydrofuran (12a) easily by flash chromatography did not allow extension of this method to an enantioselective synthesis of pyranonaphthoquinone (14). Pyranonaphthoquinone (14) is closely related to the 3C protease inhibitor thysanone (15).

  DOI：

  10.1071/ch00074

文献信息

• ——
  作者：Margaret A. Brimble、Richard J. Elliott、John F. McEwan

  DOI：10.1071/ch00074

  日期：——

  The Diels Alder addition of naphthoquinone (2a) to 1-trimethylsilyloxybuta-1,3-diene (3) afforded a 1.4 : 1 ratio of Diels Alder adducts (5a) and (6a) which were easily separated by flash chromatography. Individual treatment of adducts (5a) and (6a) with tin( IV) chloride afforded dihydrofuran (11a) as an inseparable 1 : 1 mixture of diastereomers. Diels Alder addition of naphthoquinones (2a) and (2b) to 1-methoxy-1-trimethylsilyloxybuta-1,3-diene (4) followed by treatment with tin( IV) chloride afforded dihydrofurans (12a) and (12b) respectively, both as inseparable 1 : 1 mixtures of C2 epimers. Removal of the pantolactone auxiliary from dihydrofuran (12a) was achieved by using lithium borohydride, affording aldehyde (13) which underwent oxidative rearrangement by using ceric ammonium nitrate to pyranonaphthoquinone (14). The inability to separate the individual C2 epimers of dihydrofuran (12a) easily by flash chromatography did not allow extension of this method to an enantioselective synthesis of pyranonaphthoquinone (14). Pyranonaphthoquinone (14) is closely related to the 3C protease inhibitor thysanone (15).