20-hydroxy-3,12-dioxo-25,26,27-trinor-dammaran-24-oic acid-lactone | 19667-12-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 20-hydroxy-3,12-dioxo-25,26,27-trinor-dammaran-24-oic acid-lactone
• 英文别名: 20-Hydroxy-3,12-dioxo-25,26,27-trinor-dammaran-24-saeure-lacton；(5R,8R,9R,10R,13R,14R,17S)-4,4,8,10,14-pentamethyl-17-[(2S)-2-methyl-5-oxooxolan-2-yl]-2,5,6,7,9,11,13,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,12-dione
• CAS: 19667-12-0
• 化学式: C₂₇H₄₀O₄
• 分子量: 428.612
• InChiKey: RIPHFLSMVDOKMW-OGTCUWATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (20S,24S)-epoxydammarane-3β,12β,25-triol 在 jones' reagent 作用下， 以 丙酮 为溶剂， 以70%的产率得到20-hydroxy-3,12-dioxo-25,26,27-trinor-dammaran-24-oic acid-lactone
  参考文献：
  名称：

  New Dammarane Triterpenes from the Aerial Parts of Ibicella lutea Grown in Argentina

  摘要：

  Two new dammarane triterpenes have been isolated from the aerial parts of Ibicella lutea, 3-acetyl-24-epi-polacandrin (1) and 1,3-diacetyl-24-epi-polacandrin (2), and were obtained along with the known compounds 20S*,24S*-epoxy-3beta,12beta,25-trihydroxydammarane (3) and apigenin. The structures of compounds I and 2 were deduced by spectroscopic studies and by chemical transformations leading to the preparation of derivatives 4-11. The structure and relative stereochemistry of 1 were verified by single-crystal X-ray analysis. The natural compounds and selected semisynthetic derivatives were evaluated against several tumor cells.

  DOI：

  10.1021/np030273i

文献信息

• Triterpenes from the frond exudate of the fern Notholaena greggii
  作者：Giovanni Appendino、Pierluigi Gariboldi、Eckhard Wollenweber、Angelo Sironi、Henriette Molinari

  DOI：10.1016/0031-9422(92)80040-l

  日期：1992.3

  Abstract Along with known flavonoid aglycones, the frond exudate of N. greggii yielded two ocotillol-type dammarane triterpenoids, whose structure was established by chemical reactions, spectral data and X-ray analysis.

  摘要 与已知的黄酮苷元一起，N. greggii 的叶状分泌物产生了两种 ocotillol 型达马烷三萜类化合物，其结构是通过化学反应、光谱数据和 X 射线分析确定的。
• Fischer; Seiler, Justus Liebigs Annalen der Chemie, 1959, vol. 626, p. 185,199
  作者：Fischer、Seiler

  DOI：——

  日期：——