methyl 2-methylidene-3-oxolup-20(29)-en-28-oate | 1381855-03-3

• 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 2-methylidene-3-oxolup-20(29)-en-28-oate
• 英文别名: methyl (1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-10-methylidene-9-oxo-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysene-3a-carboxylate
• CAS: 1381855-03-3
• 化学式: C₃₂H₄₈O₃
• 分子量: 480.731
• InChiKey: DXPFSBHZKGVHOE-BZCFEEOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.81
• 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 2-methylidene-3-oxolup-20(29)-en-28-oate 在 双氧水 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 48.5h， 生成 methyl (2a)-2-{[(2-hydroxyethyl)sulfonyl]methyl}-3-oxolup-20(29)en-28-oate
  参考文献：
  名称：

  Alkylidene branched lupane derivatives: Synthesis and antitumor activity

  摘要：

  Several novel alkylidene branched lupane derivatives have been prepared. Many of these compounds showed a significant cytotoxicity. The most active compound, 2-methylene-betulonic acid, showed IC50 values between 0.2 and 0.6 mu M for 15 different human cancer cell lines. Cytotoxicity can be improved by encapsulation in liposomes. These compounds act by triggering apoptotic cell death as shown by DNA-laddering experiments and acridine orange/ethidium bromide staining. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.023
• 作为产物：
  描述：

  路路通酸 在 水 、 potassium carbonate 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 30.5h， 生成 methyl 2-methylidene-3-oxolup-20(29)-en-28-oate
  参考文献：
  名称：

  Alkylidene branched lupane derivatives: Synthesis and antitumor activity

  摘要：

  Several novel alkylidene branched lupane derivatives have been prepared. Many of these compounds showed a significant cytotoxicity. The most active compound, 2-methylene-betulonic acid, showed IC50 values between 0.2 and 0.6 mu M for 15 different human cancer cell lines. Cytotoxicity can be improved by encapsulation in liposomes. These compounds act by triggering apoptotic cell death as shown by DNA-laddering experiments and acridine orange/ethidium bromide staining. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.023

文献信息

• Reaction of Methyl (2-Methylidene)-3-oxolup-20(29)-en-28-oate with Dimethyl Trimethylsilyl Phosphite
  作者：O. V. Tsepaeva、A. V. Nemtarev、T. I. Abdullin、E. V. Kuznetsova、V. F. Mironov

  DOI：10.1134/s1070363218090335

  日期：2018.9

  phosphorylation of pentacyclic triterpenoids derivatives containing an α,β-unsaturated carbonyl fragment in the ring A was described by the example of the reaction of methyl (2-methylidene)-3-oxolup-20(29)-en-28-oate with dimethyl trimethylsilyl phosphite. Methyl 2-dimethoxyphosphorylmethyl-3-oxolup-20(29)-en-28-oate was obtained as two epimers in a 2: 1 ratio in a 70% yield.

  通过甲基（2-亚甲基）-3-oxolup-20（29）-en-28-的反应实例，描述了在环A中含有α，β-不饱和羰基片段的五环三萜衍生物的磷酸化方法。与亚甲基三甲基甲硅烷基亚磷酸酯。以2：1的比例获得2-二甲氧基磷酰基甲基-3-氧杂up-20（29）-en-28-oate甲酯，产率为70％。
• Reaction of methyl 2-methylidene-3-oxolup-20(29)-en-28-oate with triphenylphosphonium trifluoromethanesulfonate
  作者：O. V. Tsepaeva、A. V. Nemtarev、V. F. Mironov

  DOI：10.1134/s1070428017040212

  日期：2017.4

  Phosphorylation of methyl 2-methylidene-3-oxolup-20(29)-en-28-oate with triphenylphosphonium trifluoromethanesulfonate in methylene chloride at 20°C afforded 90% of a γ-oxoalkylphosphonium salt containing a terpenoid fragment, [28-methoxy-3,28-dioxolup-20(29)-en-2-ylmethyl]triphenylphosphonium trifluoromethanesulfonate, as a mixture of two epimers (2S/2R) at a ratio of 2: 1.

  将三亚甲基三氟甲磺酸三苯基phosph在20°C的条件下用二氯甲烷中的2-亚甲基-3-氧甲基20-20（29）-en-28-膦酸酯进行磷酸化，得到90％的含有萜类片段的[-28-甲氧基- 3,28-dioxolup-20（29）-en-2-yl甲基]三苯基phosph三氟甲磺酸盐，为两种差向异构体（2S / 2R）的混合物，比率为2：1。
• Alkylidene branched lupane derivatives: Synthesis and antitumor activity
  作者：René Csuk、Sebastian Stark、Christoph Nitsche、Alexander Barthel、Bianka Siewert

  DOI：10.1016/j.ejmech.2012.04.023

  日期：2012.7

  Several novel alkylidene branched lupane derivatives have been prepared. Many of these compounds showed a significant cytotoxicity. The most active compound, 2-methylene-betulonic acid, showed IC50 values between 0.2 and 0.6 mu M for 15 different human cancer cell lines. Cytotoxicity can be improved by encapsulation in liposomes. These compounds act by triggering apoptotic cell death as shown by DNA-laddering experiments and acridine orange/ethidium bromide staining. (C) 2012 Elsevier Masson SAS. All rights reserved.