moradiol diacetate | 64763-00-4

• 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: moradiol diacetate
• 英文别名: 3β,28-diacetoxy-olean-18(19)-ene；3β,28-Diacetoxy-olean-18-en (Maradioldiacetat)；3β,28-diacetoxyoleanan-18(19)-ene；3β,28-diacetoxy-olean-18-ene；3β,28-Diacetoxy-olean-18-en；[(4aS,6aR,6aR,6bR,8aR,10S,12aR,14aS)-10-acetyloxy-2,2,6a,6b,9,9,12a-heptamethyl-3,4,5,6,6a,7,8,8a,10,11,12,13,14,14a-tetradecahydropicen-4a-yl]methyl acetate
• CAS: 64763-00-4
• 化学式: C₃₄H₅₄O₄
• 分子量: 526.8
• InChiKey: HIYOAXCZGBPJDS-PEZGELNCSA-N

物化性质

• 熔点：
  278.0-278.5 °C

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  38
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  moradiol diacetate 在 甲醇 、 potassium hydroxide 、 盐酸 、 水 作用下， 以 苯 为溶剂， 反应 5.0h， 以90%的产率得到3β,28-dihydroxyoleanan-18(19)-ene
  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 吡啶 、 三氯氧磷 作用下， 反应 3.0h， 以87%的产率得到moradiol diacetate
  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

文献信息

• 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.