3β,28-dihydroxyoleanan-18(19)-ene | 568-49-0

• 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: 3β,28-dihydroxyoleanan-18(19)-ene
• 英文别名: moradiol；olean-18-ene-3β,28-diol；Olean-18-en-3β,28-diol；3β,28-Dihydroxy-olean-18-en (Maradiol)；(3S,4aR,6aS,6aR,6bR,8aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,6a,7,8,9,10,13,14,14a-tetradecahydropicen-3-ol
• CAS: 568-49-0
• 化学式: C₃₀H₅₀O₂
• 分子量: 442.726
• InChiKey: AGSHKZHSGTVPDS-AFZINJQDSA-N

物化性质

• 熔点：
  221-223 °C
• 沸点：
  527.0±50.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3β,28-dihydroxyoleanan-18(19)-ene 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以78%的产率得到黄莲木酸
  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：

  3β,28-diacetoxyoleanan-19β-ol 在 三氟化硼 、 乙酸酐 作用下， 生成 3β,28-dihydroxyoleanan-18(19)-ene
  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

• Efficient synthesis of morolic acid and related triterpenes starting from betulin
  作者：Pu Zhang、Jia Hao、Jun Liu、Luyong Zhang、Hongbin Sun

  DOI：10.1016/j.tet.2009.03.100

  日期：2009.5

  Morolic acid (1) is a naturally occurring pentacyclic triterpene whose derivatives exhibit promising anti-HIV and other biological activities. An efficient synthesis of 1 has been accomplished in 11 steps with a total yield of 24% starting from betulin. Some related natural triterpenes including moradiol (4), acridocarpusic acid D (5), acridocarpusic acid E (6), and moronic aldehyde (7) have also been

  Morolic acid（1）是一种天然存在的五环三萜，其衍生物具有良好的抗HIV和其他生物活性。的有效的合成1已经结合的24％桦木醇从开始的总产11层的步骤而完成的。还合成了一些相关的天然三萜，其中包括吗啡醇（4），cri果酸D（5），carp果酸E（6）和吗啉醛（7）。生物测定的结果表明，1，5，和6表现出对糖原磷酸化酶中等抑制活性。
• Extended Triterpene Derivatives
  申请人：Nitz Theodore J.

  公开号：US20120046291A1

  公开（公告）日：2012-02-23

  The present invention concerns novel pharmaceutically active triterpene derivatives, pharmaceutical compositions containing the same, their use as medicaments, and the use of the compounds for the manufacture of specific medicaments. The present invention also concerns a method of treatment involving administration of the compounds. Specifically, the compounds are derivatives of betulinic acid having substitutions at one or more of the C-3, C2-8 and C-19 positions as further described herein. The novel compounds are useful as antiretroviral agents. In particular, the novel compounds are useful for the treatment of Human Immunodeficiency Virus (HIV).

  本发明涉及一种新型药用三萜衍生物，包含其药物组合物、其作为药物的用途以及用于制造特定药物的化合物的用途。本发明还涉及一种涉及化合物给药的治疗方法。具体来说，这些化合物是苦杏仁酸衍生物，在C-3、C2-8和C-19位置之一或多个处具有取代基，如本文所述。这些新型化合物可用作抗逆转录病毒剂。特别地，这些新型化合物可用于治疗人类免疫缺陷病毒（HIV）。
• 60. Triterpenoids. Part I. Morolic acid, a new triterpenoid sapogenin
  作者：D. H. R. Barton、C. J. W. Brooks

  DOI：10.1039/jr9510000257

  日期：——
• An efficient synthesis of moronic and heterobetulonic acids from allobetulin
  作者：El’mira F. Khusnutdinova、Natalya I. Medvedeva、Dmitri V. Kazakov、Olga S. Kukovinets、Alexander N. Lobov、Kirill Yu. Suponitsky、Oxana B. Kazakova

  DOI：10.1016/j.tetlet.2015.11.086

  日期：2016.1

  The reaction of acetoxyallobetulin with HClO4 in refluxing Ac2O led to a mixture of diacetoxyheterobetulin (3 beta,28-diacetoxy-18 alpha,19 beta H-urs-20-ene), diacetoxymoradiol (3 beta,28-diacetoxy-olean-18(19)-ene), 3 beta-acetoxy-21 beta-acetyl-20 beta,28-epoxy-18 alpha,19 beta H-ursane, and diacetoxy-delta-erythrodiol (3 beta,28-diacetoxy-olean-13(beta)-ene), which were isolated by column chromatography in yields of 18%, 37%, 39%, and 2%, respectively. Deacetylation of diacetoxyheterobetulin and diacetoxymoradiol followed by Jones oxidation of the corresponding triterpene 3 beta,28-diols led to heterobetulonic and moronic acids with overall yields of 17% and 35% from acetoxyallobetulin, respectively. The reported route makes possible the medium-to-large scale preparation of these pharmacologically important triterpenic acids. (C) 2015 Elsevier Ltd. All rights reserved.
• Klinot,J.; Vystrcil,A., Collection of Czechoslovak Chemical Communications, 1964, vol. 29, p. 516 - 530
  作者：Klinot,J.、Vystrcil,A.

  DOI：——

  日期：——