(4aS,6aR,9S,11aS,11bS)-4-methoxy-4,9,11b-trimethyl-1,4,4a,5,6,9,10,11,11a,11b-decahydro-2H-6a,9-methanocyclohepta[f]isochromen-2-one | 932046-56-5

• 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: (4aS,6aR,9S,11aS,11bS)-4-methoxy-4,9,11b-trimethyl-1,4,4a,5,6,9,10,11,11a,11b-decahydro-2H-6a,9-methanocyclohepta[f]isochromen-2-one
• CAS: 932046-56-5
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: OSIUDPGIRHEVAU-FHIHSOLGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4aS,6aR,9S,11aS,11bS)-4-methoxy-4,9,11b-trimethyl-1,4,4a,5,6,9,10,11,11a,11b-decahydro-2H-6a,9-methanocyclohepta[f]isochromen-2-one 在 Amberlyst 15 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以100%的产率得到methyl ent-2,4-seco-4-oxo-3,19-dinorbeyer-15-en-2-oate
  参考文献：
  名称：

  ent-Beyerane diterpenoids from the heartwood of Excoecaria parvifolia

  摘要：

  Chromatographic fractionations of the toluene extract of the heartwood of Excoecaria parvifolia collected in Australia resulted in the isolation of 12 beyerane diterpenes (1-12), and the triterpene, lupeol. Four of the isolated diterpenoids (5-7 and 12) have unusual structures: ent-3-oxa-beyer-15-en-2-one, (5); ent-15,16-epoxy-2-hydroxy-19-norbeyer-1,4-dien-3-one (6); methyl ent-2,4-seco-15,16-epoxy-4oxo-3,19-dinorbeyer-15-en-2-oate(7); and ent-2,17-dihydroxy-19-norbeyer-1,4,15-trien-3-one (12). The structures were established by spectroscopic analyses, NMR data comparisons with similar diterpenes, and chemical correlations. All the diterpenes are assumed. to have the same absolute configuration as the co-occurring (+)-stachenol (4). Diosphenol 2 and nor-lactone 5 exhibited significant potency in bioassays for cytotoxic activity against leukemia cells (L1210). Plausible biosynthetic pathways are proposed to explain the origin of the diterpene metabolites. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2006.11.010
• 作为产物：
  描述：

  甲醇 、 2-[(1R,4S,5S,6S,9S)-4-acetyl-5,9-dimethyl-5-tricyclo[7.2.1.01,6]dodec-10-enyl]acetic acid 在 Amberlyst 15 作用下， 反应 48.0h， 以63%的产率得到(4aS,6aR,9S,11aS,11bS)-4-methoxy-4,9,11b-trimethyl-1,4,4a,5,6,9,10,11,11a,11b-decahydro-2H-6a,9-methanocyclohepta[f]isochromen-2-one
  参考文献：
  名称：

  ent-Beyerane diterpenoids from the heartwood of Excoecaria parvifolia

  摘要：

  Chromatographic fractionations of the toluene extract of the heartwood of Excoecaria parvifolia collected in Australia resulted in the isolation of 12 beyerane diterpenes (1-12), and the triterpene, lupeol. Four of the isolated diterpenoids (5-7 and 12) have unusual structures: ent-3-oxa-beyer-15-en-2-one, (5); ent-15,16-epoxy-2-hydroxy-19-norbeyer-1,4-dien-3-one (6); methyl ent-2,4-seco-15,16-epoxy-4oxo-3,19-dinorbeyer-15-en-2-oate(7); and ent-2,17-dihydroxy-19-norbeyer-1,4,15-trien-3-one (12). The structures were established by spectroscopic analyses, NMR data comparisons with similar diterpenes, and chemical correlations. All the diterpenes are assumed. to have the same absolute configuration as the co-occurring (+)-stachenol (4). Diosphenol 2 and nor-lactone 5 exhibited significant potency in bioassays for cytotoxic activity against leukemia cells (L1210). Plausible biosynthetic pathways are proposed to explain the origin of the diterpene metabolites. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2006.11.010