oleanan-3β,19β,28-triol | 1000296-73-0

• 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: oleanan-3β,19β,28-triol
• 英文别名: 19β-machaerocerol；18α-oleanane-3β,19β,28-triol；18α-Oleanan-3β,19β,28-triol；(1R,4aR,6aR,6aR,6bR,8aR,10S,12aR,14aR,14bR)-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14,14a,14b-hexadecahydropicene-1,10-diol
• CAS: 1000296-73-0
• 化学式: C₃₀H₅₂O₃
• 分子量: 460.741
• InChiKey: IIFWNQPUNKWPRE-HWNNWUPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  oleanan-3β,19β,28-triol 、 乙酸酐 在 吡啶 作用下， 反应 2.5h， 以93%的产率得到3β,28-diacetoxyoleanan-19β-ol
  参考文献：
  名称：

  Synthesis of olean-18(19)-ene derivatives from betulin

  摘要：

  The rare olean-18(19)-ene triterpenoids moradiol and moronic acid were synthesized from betulin, and their antiviral properties were investigated.

  DOI：

  10.1134/s1068162009020125
• 作为产物：
  描述：

  28-oxoallobetulin 在 四氢呋喃 、 chromium(VI) oxide 、 lithium aluminium tetrahydride 、 氯仿 、 溶剂黄146 作用下， 生成 oleanan-3β,19β,28-triol
  参考文献：
  名称：

  Davy et al., Journal of the Chemical Society, 1951, p. 2702,2705

  摘要：

  DOI：

文献信息

• Useful approach to access germanicanes from betulin
  作者：Dominic Thibeault、Jean Legault、Jimmy Bouchard、André Pichette

  DOI：10.1016/j.tetlet.2007.09.171

  日期：2007.11

  A new semisynthetic access to germanicane-type triterpenes was achieved from betulin, a natural triterpene of the lupane family. The Wagner-Meerwein rearrangement of acetylated betulinic acid allowed the formation of the typical ring E of germanicanes and a lactone function. Several germanicane derivatives can be obtained via the lactone ring-opening such as 19 beta-machaerocerol and 19 beta-machaeroceric acid. The cytotoxicity of some compounds was evaluated against two cancerous cell lines. Crown Copyright (c) 2007 Published by Elsevier Ltd. All rights reserved.
• Vystrcil et al., Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 3279,3284
  作者：Vystrcil et al.

  DOI：——

  日期：——