A-nor-5βH-19β,28-epoxy-18α-olean-3-one | 107436-52-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: A-nor-5βH-19β,28-epoxy-18α-olean-3-one
• 英文别名: 19β,28-epoxy-4,23,24-trinor-5β-A-neo-18α-olean-3-one；allobetulin 5βH-norketone；(1R,4R,5R,8S,12R,13R,16R,17R,18R)-4,5,12,19,19-pentamethyl-23-oxahexacyclo[16.3.2.01,17.04,16.05,13.08,12]tricosan-9-one
• CAS: 107436-52-2
• 化学式: C₂₇H₄₂O₂
• 分子量: 398.629
• InChiKey: UWBPSDCYSHEQGU-UTTZMRHLSA-N

物化性质

• 熔点：
  213 °C
• 沸点：
  486.5±45.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  29
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  A-nor-5βH-19β,28-epoxy-18α-olean-3-one 在 羟胺 作用下， 以 吡啶 为溶剂， 反应 2.0h， 以85%的产率得到A-nor-5βH-19β,28-epoxy-18α-olean-3-oxime
  参考文献：
  名称：

  Synthetic Transformations of Higher Terpenoids: XI. Synthesis of A-Nor-5bH-19b,28-epoxy-18a-olean-3-one Derivatives

  摘要：

  Starting with allobetulin triterpenoid A-nor-derivatives with a cis-junction of A/B rings were prepared for the first time.

  DOI：

  10.1023/b:rujo.0000045887.67489.44
• 作为产物：
  描述：

  A-nor-5αH-19β,28-epoxy-18α-olean-3-ene 在 臭氧 、 锌 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 1.0h， 以62%的产率得到A-nor-5βH-19β,28-epoxy-18α-olean-3-one
  参考文献：
  名称：

  Synthetic Transformations of Higher Terpenoids: XI. Synthesis of A-Nor-5bH-19b,28-epoxy-18a-olean-3-one Derivatives

  摘要：

  Starting with allobetulin triterpenoid A-nor-derivatives with a cis-junction of A/B rings were prepared for the first time.

  DOI：

  10.1023/b:rujo.0000045887.67489.44

文献信息

• Synthesis and cytotoxicity of allobetulin derivatives
  作者：O. B. Kazakova、I. E. Smirnova、E. F. Khusnutdinova、O. S. Zhukova、L. V. Fetisova、G. N. Apryshko、N. I. Medvedeva、E. Yu. Yamansarov、I. P. Baikova、Thanh Tra Nguyen、H. Do Thi Thu

  DOI：10.1134/s1068162014050082

  日期：2014.9

  The synthesis and screening of antitumor activity in vitro (cytotoxicity) of various oxygen, nitrogen, sulfur and platinum-containing derivatives of allobetulin, including different arrangements of the double bonds in the A and B rings, penta- and hexacyclic ring A, 21-acetyl-20,28-epoxy-18α,19βH-ursane-isomeric cycle E, was carry out. (3R,5R)-19β,28-Epoxy-4,5-seco-18α-olean-3(5)-ozonide and 2,3-i

  合成和筛选多种别氧白蛋白的含氧，氮，硫和铂的体外抗肿瘤活性（细胞毒性），包括A和B环，五环和六环A，21-进行了乙酰基-20,28-环氧-18α，19βH-ur烷异构体循环E。（3R，5R）-19β，28-环氧-4,5-seco-18α-olean-3（5）-臭氧化物和2,3-吲哚-21β-乙酰基-20β，28-环氧-18α，H-19β -ursane适当地显示了对黑色素瘤MeWo和白血病SR细胞的显着细胞毒活性。第一化合物的（3S，5S）-非对映异构体没有显示细胞毒性。
• Synthesis of 19β,28-epoxy-23,24-dinor-A-neo-18α-olean-4-en-3-one from betulin
  作者：N. I. Medvedeva、O. B. Flekhter、O. S. Kukovinets、F. Z. Galin、G. A. Tolstikov、I. Baglin、C. Cavé

  DOI：10.1007/s11172-007-0125-x

  日期：2007.4

  19β,28-Epoxy-23,24-dinor-A-neo-18α-olean-4-en-3-one was obtained from betulin in a total yield of 18%.

  从中获得了19β,28-环氧-23,24-双降-A-新-18α-油烯-4-烯-3-酮，总产率为18%，该化合物来源自羽扇豆醇。
• Synthesis of new cyanoethyl derivatives from 3-oxotriterpenoids
  作者：E. F. Khusnutdinova、А. V. Petrova、А. I. Poptsov、А. N. Lobov、I. E. Smirnova、О. S. Kukovinets

  DOI：10.1134/s1070428017080073

  日期：2017.8

  Reaction of 3-oxotriterpenoids and steroids with acrylonitrile in the presence of BnEt3NCl and 30% KOH in dioxane proceeds with the formation of 2,2-biscyanoethyl derivatives substituted in the alpha-position to 3-oxo group. In the presence of several alpha-hydrogen atoms at the 3-oxo group the reaction of cyanoethylation involved the positions C (4) and C (5) , leading to 2,2,5-tricyanoethyl and 2,4-dicyanoethyl derivatives. The cyanoethylation of tetracyclic compounds occurred with the formation of monocyanoethyl derivatives with an overall increase in the yield.
• Synthetic Transformations of Higher Terpenoids: XI. Synthesis of A-Nor-5bH-19b,28-epoxy-18a-olean-3-one Derivatives
  作者：N. I. Medvedeva、O. B. Flekhter、E. V. Tretyakova、F. Z. Galin、L. A. Baltina、L. V. Spirikhin、G. A. Tolstikov

  DOI：10.1023/b:rujo.0000045887.67489.44

  日期：2004.8

  Starting with allobetulin triterpenoid A-nor-derivatives with a cis-junction of A/B rings were prepared for the first time.