17β-hydroxy-7α-(5'-methyl-2'-furyl)-3-oxo-pregn-4-ene-21-carboxylic acid γ-lactone

• 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: 17β-hydroxy-7α-(5'-methyl-2'-furyl)-3-oxo-pregn-4-ene-21-carboxylic acid γ-lactone
• 英文别名: (7R,8R,9S,10R,13S,14S,17R)-10,13-dimethyl-7-(5-methylfuran-2-yl)spiro[2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-17,5'-oxolane]-2',3-dione
• 化学式: C₂₇H₃₄O₄
• 分子量: 422.565
• InChiKey: LDLZGGXORNDAPA-CAPKTMDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  31
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲基呋喃 、 坎利酮 在 乙醇 、 三氟化硼乙醚 作用下， 以 硝基甲烷 为溶剂， 反应 17.0h， 以69.5%的产率得到17β-hydroxy-7α-(5'-methyl-2'-furyl)-3-oxo-pregn-4-ene-21-carboxylic acid γ-lactone
  参考文献：
  名称：

  A New Approach to the Furan Degradation Problem Involving Ozonolysis of the trans-Enedione and Its Use in a Cost-Effective Synthesis of Eplerenone

  摘要：

  Whereas ozonization of furan 3a affords little or no carboxylic acid 5, ozonization of the corresponding trans-enedione 6 afforded carboxylic acid 5 in 82.4% yield (cryst., overall from furan, 100 g scale; after workup with dimethyl sulfide, followed by mildly basic hydrogen peroxide). This new approach to furan degradation is showcased in a cost-effective synthesis of eplerenone, an important new medicine for cardiovascular indications.

  DOI：

  10.1021/ol060503v

文献信息

• 7a-Furyl or thienyl-substituted steroid compounds
  申请人：Pearlman Allen Bruce

  公开号：US20070106072A1

  公开（公告）日：2007-05-10

  The present invention involves intermediates, including a 7α-substituted steroid (II), and processes which are used to prepare eplerenone, a useful pharmaceutical agent.
• A New Approach to the Furan Degradation Problem Involving Ozonolysis of the <i>trans</i>-Enedione and Its Use in a Cost-Effective Synthesis of Eplerenone
  作者：Bruce A. Pearlman、Amphlett G. Padilla、John T. Hach、Jeffrey L. Havens、Muniraj D. Pillai

  DOI：10.1021/ol060503v

  日期：2006.5.1

  Whereas ozonization of furan 3a affords little or no carboxylic acid 5, ozonization of the corresponding trans-enedione 6 afforded carboxylic acid 5 in 82.4% yield (cryst., overall from furan, 100 g scale; after workup with dimethyl sulfide, followed by mildly basic hydrogen peroxide). This new approach to furan degradation is showcased in a cost-effective synthesis of eplerenone, an important new medicine for cardiovascular indications.