(20S)-20-ethenyl-5α-pregn-2-en-6-one | 128609-25-6

• 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: (20S)-20-ethenyl-5α-pregn-2-en-6-one
• 英文别名: (5S,8S,9S,10R,13R,14S,17R)-17-[(2R)-but-3-en-2-yl]-10,13-dimethyl-1,4,5,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-6-one
• CAS: 128609-25-6
• 化学式: C₂₃H₃₄O
• 分子量: 326.522
• InChiKey: PQWXMYWCOWGOIM-VTAKWGFLSA-N

物化性质

• 沸点：
  416.7±24.0 °C(Predicted)
• 密度：
  0.996±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (20S)-20-ethenyl-5α-pregn-2-en-6-one 、 3-氯苯乙烯 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以70%的产率得到(22E)-23-(3-chlorophenyl)-24-nor-5α-chola-2,22-dien-6-one
  参考文献：
  名称：

  Synthesis of novel aryl brassinosteroids through alkene cross-metathesis and preliminary biological study

  摘要：

  A series of phenyl analogues of brassinosteroids was prepared via alkene cross-metathesis using commercially available styrenes and 24-nor-5cc-chola-2,22-dien-6-one. All derivatives were successfully docked into the active site of BRIJ. using AutoDock Vina. Plant growth promoting activity was measured using the pea inhibition biotest and Arabidopsis root sensitivity assay and then was compared with naturally occuring brassinosteroids. Differences in the production of plant hormone ethylene were also observed in etiolated pea seedlings after treatment with the new and also five known brassinosteroid phenyl analogues. Antiproliferative activity was also studied using normal human fibroblast and human cancer cell lines.

  DOI：

  10.1016/j.steroids.2017.08.010
• 作为产物：
  描述：

  (20S)-6,6-ethylendioxy-5α-pregn-2-en-6-one 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以96%的产率得到(20S)-20-ethenyl-5α-pregn-2-en-6-one
  参考文献：
  名称：

  基于烯烃交叉复分解和初步生物学评估的氟化油菜素甾体的合成

  摘要：

  通过使用带有不同（全氟烷基）丙烯的带有末端烯烃部分的油菜甾体衍生物的烯烃交叉复分解，合成了具有全氟烷基化侧链的三种类型的油菜甾体类似物。交叉复分解产物中双键的存在允许进行简单的一步双二羟基化反应，以提供中间体，该中间体在Baeyer-Villiger氧化后可提供目标化合物。在GABA A受体，细胞毒性和油菜素内酯活性中测试了制备的类似物的生物学活性，在某些情况下，这些活性达到了与它们的非氟化类似物相同的范围。

  DOI：

  10.1021/jm900495f

文献信息

• Synthesis of novel aryl brassinosteroids through alkene cross-metathesis and preliminary biological study
  作者：Petra Korinkova、Vaclav Bazgier、Jana Oklestkova、Lucie Rarova、Miroslav Strnad、Miroslav Kvasnica

  DOI：10.1016/j.steroids.2017.08.010

  日期：2017.11

  A series of phenyl analogues of brassinosteroids was prepared via alkene cross-metathesis using commercially available styrenes and 24-nor-5cc-chola-2,22-dien-6-one. All derivatives were successfully docked into the active site of BRIJ. using AutoDock Vina. Plant growth promoting activity was measured using the pea inhibition biotest and Arabidopsis root sensitivity assay and then was compared with naturally occuring brassinosteroids. Differences in the production of plant hormone ethylene were also observed in etiolated pea seedlings after treatment with the new and also five known brassinosteroid phenyl analogues. Antiproliferative activity was also studied using normal human fibroblast and human cancer cell lines.
• Synthesis of Fluorinated Brassinosteroids Based on Alkene Cross-Metathesis and Preliminary Biological Assessment
  作者：Barbara Eignerová、Barbora Slavíková、Miloš Buděšínský、Martin Dračínský、Blanka Klepetářová、Eva Št’astná、Martin Kotora

  DOI：10.1021/jm900495f

  日期：2009.9.24

  Three types of brassinosteroid analogues with perfluoroalkylated side chains were synthesized by using alkene cross-metathesis of a brassinosteroid derivative bearing a terminal alkene moiety with different (perfluoroalkyl)propenes. The presence of the double bonds in the cross-metathesis products allowed a facile one-step double dihydroxylation to provide intermediates that after Baeyer−Villiger oxidation

  通过使用带有不同（全氟烷基）丙烯的带有末端烯烃部分的油菜甾体衍生物的烯烃交叉复分解，合成了具有全氟烷基化侧链的三种类型的油菜甾体类似物。交叉复分解产物中双键的存在允许进行简单的一步双二羟基化反应，以提供中间体，该中间体在Baeyer-Villiger氧化后可提供目标化合物。在GABA A受体，细胞毒性和油菜素内酯活性中测试了制备的类似物的生物学活性，在某些情况下，这些活性达到了与它们的非氟化类似物相同的范围。