methyl (4β)-3,11-dioxo-urs-1,12-dien-24-oate

• 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: methyl (4β)-3,11-dioxo-urs-1,12-dien-24-oate
• 英文别名: methyl (4R,4aR,6aR,6bS,8aR,11R,12S,12aR,14aR,14bS)-4,6a,6b,8a,11,12,14b-heptamethyl-3,14-dioxo-5,6,7,8,9,10,11,12,12a,14a-decahydro-4aH-picene-4-carboxylate
• 化学式: C₃₁H₄₄O₄
• 分子量: 480.688
• InChiKey: PZTLSKJTDWXGGS-XKVIHBILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  乙酰基-11-酮基-beta-乳香酸 在 selenium(IV) oxide 、 草酰氯 、 乙酸酐 、 caesium carbonate 、 二甲基亚砜 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 38.5h， 生成 methyl (4β)-3,11-dioxo-urs-1,12-dien-24-oate
  参考文献：
  名称：

  Oxidative and reductive transformations of 11-keto-β-boswellic acid

  摘要：

  Extraction of frankincense-a fragrant resin obtained from plants of the genus Boswellia followed by an oxidation furnished high yields of (313) 3-O-acetyl-11-keto-beta-boswellic acid (beta-AKBA), a valuable starting material for accessing boswellic acid derivatives. Boswellic acids are fascinating triterpenoic acids that exhibit different biological activities. However, their biological potential, as well as that of their derivatives, remained unexploited due to their limited availability. In this study we were able to prepare derivatives of 11-keto-beta-boswellic acid in good to excellent yields by oxidative and reductive transformations mainly in rings A and C of the triterpenoid skeleton. Among other transformations, a highly cytotoxic endoperoxide was obtained in excellent yields. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.01.062

文献信息

• Oxidative and reductive transformations of 11-keto-β-boswellic acid
  作者：René Csuk、Anja Barthel-Niesen、Dieter Ströhl、Ralph Kluge、Christoph Wagner、Ahmed Al-Harrasi

  DOI：10.1016/j.tet.2015.01.062

  日期：2015.4

  Extraction of frankincense-a fragrant resin obtained from plants of the genus Boswellia followed by an oxidation furnished high yields of (313) 3-O-acetyl-11-keto-beta-boswellic acid (beta-AKBA), a valuable starting material for accessing boswellic acid derivatives. Boswellic acids are fascinating triterpenoic acids that exhibit different biological activities. However, their biological potential, as well as that of their derivatives, remained unexploited due to their limited availability. In this study we were able to prepare derivatives of 11-keto-beta-boswellic acid in good to excellent yields by oxidative and reductive transformations mainly in rings A and C of the triterpenoid skeleton. Among other transformations, a highly cytotoxic endoperoxide was obtained in excellent yields. (C) 2015 Elsevier Ltd. All rights reserved.