3-ethoxy-6-formyl-17α-methyl-3,5-pregnadien-20-one

• 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: 3-ethoxy-6-formyl-17α-methyl-3,5-pregnadien-20-one
• 英文别名: 17α-methyl-6-formyl-3-ethoxy-3,5-pregnadien-20-one；(8R,9S,10R,13S,14S,17S)-17-acetyl-3-ethoxy-10,13,17-trimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthrene-6-carbaldehyde
• 化学式: C₂₅H₃₆O₃
• 分子量: 384.559
• InChiKey: SGXKCQWADFWWBS-LAASSQBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-ethoxy-6-formyl-17α-methyl-3,5-pregnadien-20-one 在 sodium tetrahydroborate 、 硫酸 作用下， 以 乙醇 为溶剂， 以94%的产率得到17α-Methyl-6-methylene-4-pregnen-3,20-dione
  参考文献：
  名称：

  Crystallographic and spectroscopic study on a known orally active progestin

  摘要：

  6,17 alpha-Dimethyl-4,6-pregnadiene-3,20-dione (medrogestone, 2) is for a long time known steroid endowed with progestational activity. In order to study its crystallographic and NMR spectroscopic properties with the aim to fill the literature gap, we prepared medrogestone following a traditional procedure. A careful NMR study allowed the complete assignment of the H-1 and C-13 NMR signals not only of medrogestone but also of its synthetic intermediates. The structural and stereochemical characterizations of medrogestone together with its precursor 17 alpha-methyl-3-ethoxy-pregna-3,5-dien-20-one were described by means of X-ray analysis, allowing a deepened conformational investigation. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2015.09.007
• 作为产物：
  描述：

  17α-methyl-3-ethoxy-pregna-3,5-dien-20-one 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 以77%的产率得到3-ethoxy-6-formyl-17α-methyl-3,5-pregnadien-20-one
  参考文献：
  名称：

  Crystallographic and spectroscopic study on a known orally active progestin

  摘要：

  6,17 alpha-Dimethyl-4,6-pregnadiene-3,20-dione (medrogestone, 2) is for a long time known steroid endowed with progestational activity. In order to study its crystallographic and NMR spectroscopic properties with the aim to fill the literature gap, we prepared medrogestone following a traditional procedure. A careful NMR study allowed the complete assignment of the H-1 and C-13 NMR signals not only of medrogestone but also of its synthetic intermediates. The structural and stereochemical characterizations of medrogestone together with its precursor 17 alpha-methyl-3-ethoxy-pregna-3,5-dien-20-one were described by means of X-ray analysis, allowing a deepened conformational investigation. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2015.09.007

文献信息

• Process for preparing medrogestone
  申请人：Moutou Jean-Luc

  公开号：US20060178520A1

  公开（公告）日：2006-08-10

  A method for preparing medrogestone by heterogeneously palladium-catalyzed isomerization from 17α-methyl-6-methylenepregn-4-ene-3,20-dione.

  一种通过异质钯催化异构化 17α-甲基-6-亚甲基孕甾-4-烯-3,20-二酮制备甲孕酮的方法。
• WO2006/77209
  申请人：——

  公开号：——

  公开（公告）日：——
• METHOD FOR PREPARING MEDROGESTONE
  申请人：Solvay Pharmaceuticals GmbH

  公开号：EP1841778A1

  公开（公告）日：2007-10-10
• [EN] METHOD FOR PREPARING MEDROGESTONE<br/>[FR] METHODE DE PREPARATION DE MEDROGESTONE
  申请人：SOLVAY PHARM GMBH

  公开号：WO2006077209A1

  公开（公告）日：2006-07-27

  [EN] A method for the preparation of medrogestone by heterogeneously palladium- catalysed isomerisation from 17-methyl-6-methylenepregn-4-ene-3,20-dione is described.
  [FR] L'invention concerne une méthode de préparation de médrogestone par isomérisation catalysée au palladium de 17-méthyl-6-méthylènepregn-4-ène-3,20-dione.
• Crystallographic and spectroscopic study on a known orally active progestin
  作者：Patrizia Ferraboschi、Pierangela Ciuffreda、Samuele Ciceri、Paride Grisenti、Carlo Castellano、Fiorella Meneghetti

  DOI：10.1016/j.steroids.2015.09.007

  日期：2015.12

  6,17 alpha-Dimethyl-4,6-pregnadiene-3,20-dione (medrogestone, 2) is for a long time known steroid endowed with progestational activity. In order to study its crystallographic and NMR spectroscopic properties with the aim to fill the literature gap, we prepared medrogestone following a traditional procedure. A careful NMR study allowed the complete assignment of the H-1 and C-13 NMR signals not only of medrogestone but also of its synthetic intermediates. The structural and stereochemical characterizations of medrogestone together with its precursor 17 alpha-methyl-3-ethoxy-pregna-3,5-dien-20-one were described by means of X-ray analysis, allowing a deepened conformational investigation. (C) 2015 Elsevier Inc. All rights reserved.