methyl ent-2,4-seco-4-oxo-3,19-dinorbeyer-15-en-2-oate | 209971-40-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl ent-2,4-seco-4-oxo-3,19-dinorbeyer-15-en-2-oate
• 英文别名: methyl 2-[(1R,4S,5S,6S,9S)-4-acetyl-5,9-dimethyl-5-tricyclo[7.2.1.01,6]dodec-10-enyl]acetate
• CAS: 209971-40-4
• 化学式: C₁₉H₂₈O₃
• 分子量: 304.43
• InChiKey: YTPMQRDFWPIPIO-CGHHPOIWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl ent-2,4-seco-4-oxo-3,19-dinorbeyer-15-en-2-oate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以88%的产率得到methyl ent-2,4-seco-15,16-epoxy-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：

  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， 以 甲醇 为溶剂， 反应 120.0h， 生成 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

文献信息

• Acid metabolites from Spirostachys africana
  作者：Namboole Moses Munkombwe、Neil Arthur Hughes、Zvitendo James Duri

  DOI：10.1016/s0031-9422(97)00792-9

  日期：1998.4

  Two acid metabolites, ent-2,3-seco-beyer-15-ene-2,3-dioic acid and ent-2,4-seco-4-oxo-norbeyer-15-en-2-oic acid, have been isolated and identified by spectroscopic methods. (C) 1998 Elsevier Science Ltd. All rights reserved.
• ent-Beyerane diterpenoids from the heartwood of Excoecaria parvifolia
  作者：Mary H. Grace、Juan A. Faraldos、Mary Ann Lila、Robert M. Coates

  DOI：10.1016/j.phytochem.2006.11.010

  日期：2007.2

  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.