4-nitrocanrenone

• 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: 4-nitrocanrenone
• 英文别名: (8R,9S,10R,13S,14S,17R)-10,13-dimethyl-4-nitrospiro[2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17,5'-oxolane]-2',3-dione
• 化学式: C₂₂H₂₇NO₅
• 分子量: 385.46
• InChiKey: VHYHZMKQQRCTAZ-MHOJGGENSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  坎利酮 在 硝酸 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以52%的产率得到4-nitrocanrenone
  参考文献：
  名称：

  The nitration of canrenone with acetic anhydride/nitric acid

  摘要：

  3-Oxo-17 alpha-pregna-4,6-diene-21,17-carbolactone (canrenone, II) is produced from the potassium salt of 17-hydroxy-3-oxo-17 alpha-pregna-4,6-diene-21-carboxylic acid (I) by acid catalyzed lactonization. II reacts with acetic anhydride/nitric acid to give one main product (III) and some minor products. The structure of III was determined by chemical and spectral analysis to be the 4-nitro derivative of canrenone. This result is in contrast to the known reactions of II with most other reagents that were found to add at Delta(6). and also in contrast to the reactions of acetic anhydride/nitric acid with alkenes. Electrophilic substitution at the ambident C4 is discussed as the reaction pain. The 4-nitro group enhances the inhibitory activity of II against Na+/K+-ATPase, the target enzyme of the cardioactive digitalis glycosides, which appears to indicate increased cardioactivity. (C) 1997 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00073-1

文献信息

• The nitration of canrenone with acetic anhydride/nitric acid
  作者：Rudolf Megges、Jürgen Weiland、Bernd Undeutsch、Horst Büchting、Rudolf Schön

  DOI：10.1016/s0039-128x(97)00073-1

  日期：1997.12

  3-Oxo-17 alpha-pregna-4,6-diene-21,17-carbolactone (canrenone, II) is produced from the potassium salt of 17-hydroxy-3-oxo-17 alpha-pregna-4,6-diene-21-carboxylic acid (I) by acid catalyzed lactonization. II reacts with acetic anhydride/nitric acid to give one main product (III) and some minor products. The structure of III was determined by chemical and spectral analysis to be the 4-nitro derivative of canrenone. This result is in contrast to the known reactions of II with most other reagents that were found to add at Delta(6). and also in contrast to the reactions of acetic anhydride/nitric acid with alkenes. Electrophilic substitution at the ambident C4 is discussed as the reaction pain. The 4-nitro group enhances the inhibitory activity of II against Na+/K+-ATPase, the target enzyme of the cardioactive digitalis glycosides, which appears to indicate increased cardioactivity. (C) 1997 by Elsevier Science Inc.