10-hydroxy-7,9-dimethoxy-3-methyl-1H-benzo[g]isochromen-1-on-9-O-methyllactone | 71602-63-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 10-hydroxy-7,9-dimethoxy-3-methyl-1H-benzo[g]isochromen-1-on-9-O-methyllactone
• 英文别名: 10-hydroxy-7,9-dimethoxy-3-methyl-1H-naphtho<2,3-c>pyran-1-one；toralactone monomethyl ether B；9-O-methyl-toralactone；1H-Naphtho[2,3-c]pyran-1-one, 10-hydroxy-7,9-dimethoxy-3-methyl-；10-hydroxy-7,9-dimethoxy-3-methylbenzo[g]isochromen-1-one
• CAS: 71602-63-6
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: ZMOKQROEDAOWTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  10-hydroxy-7,9-dimethoxy-3-methyl-1H-benzo[g]isochromen-1-on-9-O-methyllactone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以85%的产率得到决明内酯
  参考文献：
  名称：

  Total Synthesis of the Antiallergic Naphtho-α-pyrone Tetraglucoside, Cassiaside C₂, Isolated from Cassia Seeds

  摘要：

  Toralactone 9-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (1, cassiaside C-2) isolated from Cassia obtusifolia L. and showing strong antiallergic activity, was concisely synthesized employing glycosyl trifluoroacetimidates as glycosylation agents. The unique naphtho-alpha-pyrone structure of toralactone (5) was constructed by condensation of orsellinate 8 with pyrone 9 in the presence of LDA as developed by Staunton and co-workers. The naphthol of toralactone showed minimal reactivity as an acceptor and was screened with various glycosyl donors. It is finally concluded that sacrifice of an excess amount of the trifluoroacetimidate or trichloroacetimidate donors (6f/6g, 6.0 equiv) in the presence of a catalytic amount of TMSOTf (0.05 and 0.3 equiv, respectively) afforded excellent yields of the coupling product, which was otherwise only a minor product under a variety of conditions examined.

  DOI：

  10.1021/jo034223u
• 作为产物：
  描述：

  4-(2-methoxycarbonyl-3,5-dimethoxybenzyl)-6-methyl-2H-pyran-2-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以20%的产率得到10-hydroxy-7,9-dimethoxy-3-methyl-1H-benzo[g]isochromen-1-on-9-O-methyllactone
  参考文献：
  名称：

  Leeper, Finian J.; Staunton, James, Journal of the Chemical Society. Perkin transactions I, 1984, # 5, p. 1053 - 1059

  摘要：

  DOI：

文献信息

• Synthesis of the Pyranonaphthoquinones Dehydroherbarin, (+)-Astropa­quinone B and (+)-Astropaquinone C en Route to Ascomycones A and B
  作者：Margaret Brimble、Andrew Wadsworth、Jonathan Sperry

  DOI：10.1055/s-0029-1218832

  日期：2010.8

  The total syntheses of the pyranonaphthoquinone natural products dehydroherbarin, (+)-astropaquinone B and (+)-astropa­quinone C are described. A late stage oxidation strategy employed for the synthesis of the astropaquinones was not amenable to the conversion of dehydroherbarin into the ascomycones. The syntheses of astropaquinones B and C reported herein constitute the first total syntheses and their absolute stereochemistry was determined to be (1R,3S).

  本文描述了脱氢草霉素（dehydroherbarin）、(+)-星棘醌B（(+)-astropaquinone B）和(+)-星棘醌C（(+)-astropaquinone C）三种吡喃萘醌天然产物分子的全合成。在合成星棘醌时使用的后期氧化策略，不适用于将脱氢草霉素转化为囊霉醌（ascomycones）。本文报道的星棘醌B和C的合成是它们的首次全合成，且它们的绝对构型被确定为(1R,3S)。
• Carpenter, T. Adrian; Evans, Geoffrey E.; Leeper, Finian J., Journal of the Chemical Society. Perkin transactions I, 1984, # 5, p. 1043 - 1051
  作者：Carpenter, T. Adrian、Evans, Geoffrey E.、Leeper, Finian J.、Staunton, James、Wilkinson, Michael R.

  DOI：——

  日期：——
• Deshpande; Khan; Ayyangar, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 9, p. 965 - 966
  作者：Deshpande、Khan、Ayyangar

  DOI：——

  日期：——
• EVANS J. E.; LEEPER F. J.; MURPHY J. A.; STAUNTON J., J. CHEM. SOC. CHEM. COMMUN., 1979, NO 5, 205-206
  作者：EVANS J. E.、 LEEPER F. J.、 MURPHY J. A.、 STAUNTON J.

  DOI：——

  日期：——
• Leeper, Finian J.; Staunton, James, Journal of the Chemical Society. Perkin transactions I, 1984, # 5, p. 1053 - 1059
  作者：Leeper, Finian J.、Staunton, James

  DOI：——

  日期：——