Betulin-dibenzoat | 5354-50-7

• 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: Betulin-dibenzoat
• 英文别名: [(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-benzoyloxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-3a-yl]methyl benzoate
• CAS: 5354-50-7
• 化学式: C₄₄H₅₈O₄
• 分子量: 650.942
• InChiKey: CNRYTEIFPWUNMB-INHZEBIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  48
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Betulin-dibenzoat 在 臭氧 、 盐酸 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以43%的产率得到20-oxo-29-norlupane-3β,28-diyl dibenzoate
  参考文献：
  名称：

  Synthesis of 30-Bromo- and 30-Azido-20-oxo-29-nor-3β,28-diacylbetulin Derivatives

  摘要：

  Ozonolysis of 3 beta, 28-diacyloxylup-20,29-enes gave 20-oxo-29-nor-3 beta,28-diacyloxylup-20,29-enes, which were brominated with molecular bromine in AcOH to obtain a mixture of 30-bromo- and 30-dibromo derivatives. Ozonolysis of 30-bromo-3 beta,28-diacylbetulin produced 29-nor-30-bromoketones, whose reaction with sodium azide afforded 29-nor-30-azidoketones of the lupane series.

  DOI：

  10.1134/s1070428019110150
• 作为产物：
  描述：

  白桦脂醇 、 苯甲酸 反应 0.08h， 以89%的产率得到Betulin-dibenzoat
  参考文献：
  名称：

  Synthesis of Betulin Dibenzoate and Diphthalate

  摘要：

  将白桦脂与苯甲酸和邻苯二甲酸的熔体在 190-200°C 的温度下反应 5 分钟，首次合成了白桦脂-3,28-二苯甲酸酯和-3,28-二邻苯二甲酸酯。

  DOI：

  10.1007/s10600-017-1976-5

文献信息

• Synthesis and in vitro antitumor evaluation of betulin acid ester derivatives as novel apoptosis inducers
  作者：Sheng-Jie Yang、Ming-Chuan Liu、Hong-Mei Xiang、Qi Zhao、Wei Xue、Song Yang

  DOI：10.1016/j.ejmech.2015.08.004

  日期：2015.9

  Nineteen betulin derivatives modified at the C-3 and C-28 positions were synthesized and assessed for antitumor activities against the MGC-803, PD, Bcap-37, A375, and MCF-7 human cancer cell lines in vitro by MU assay. Some derivatives (compounds 3a-3d and 5) displayed strong antitumor properties, with IC50 values between 4 and 18 mu M. Compound 3c, containing piperidine group at C-28 position, had IC50 values of 4.3, 4.5, 5.2, 7.5, and 5.2 mu M on the five cancer cell lines, respectively. Subsequent fluorescence staining and flow cytometric analysis indicated that compound 3c induced apoptosis in MGC-803 cell line, with an apoptosis ratio of 31.11% after 36 h of treatment at 10 mu M 3c. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Ferrocenyltriazoles from 3β,28-Diacylbetulin: Synthesis and Cytotoxic Activity
  作者：V. A. Glushkov、D. A. Shemyakina、N. K. Zhukova、L. V. Pavlogradskaya、M. V. Dmitriev、D. V. Eroshenko、A. R. Galeev、I. G. Mokrushin

  DOI：10.1134/s1070428019110083

  日期：2019.11

  The reaction of 30-bromo-3 beta,28-diacylbetulin with sodium azide afforded 30-azido-3 beta,28-diacyloxylup-20(29)-enes. The products were subjected to a CuI/TMEDA-catalyzed click reaction with ethynylferrocene to obtain the corresponding ferrocene-betulin conjugates with a 1,2,3-triazole linker.
• Synthesis and heterocyclization of triterpenic 1,3-diketones
  作者：Mikhail A. Nazarov、Irina A. Tolmacheva、Victoria V. Grishko

  DOI：10.24820/ark.5550190.p011.344

  日期：——
• Synthesis of Betulin Dibenzoate and Diphthalate
  作者：V. A. Levdanskii、A. V. Levdanskii、B. N. Kuznetsov

  DOI：10.1007/s10600-017-1976-5

  日期：2017.3

  Betulin-3,28-dibenzoate and -3,28-diphthalate were synthesized for the first time by reacting betulin with melts of benzoic and phthalic acids at 190–200°C for 5 min.

  将白桦脂与苯甲酸和邻苯二甲酸的熔体在 190-200°C 的温度下反应 5 分钟，首次合成了白桦脂-3,28-二苯甲酸酯和-3,28-二邻苯二甲酸酯。
• Synthesis of 30-Bromo- and 30-Azido-20-oxo-29-nor-3β,28-diacylbetulin Derivatives
  作者：V. A. Glushkov、D. A. Schemyakina、N. K. Zhukova

  DOI：10.1134/s1070428019110150

  日期：2019.11

  Ozonolysis of 3 beta, 28-diacyloxylup-20,29-enes gave 20-oxo-29-nor-3 beta,28-diacyloxylup-20,29-enes, which were brominated with molecular bromine in AcOH to obtain a mixture of 30-bromo- and 30-dibromo derivatives. Ozonolysis of 30-bromo-3 beta,28-diacylbetulin produced 29-nor-30-bromoketones, whose reaction with sodium azide afforded 29-nor-30-azidoketones of the lupane series.