17α-acetoxy-6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid | 101916-26-1

• 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: 17α-acetoxy-6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid
• 英文别名: (6S,8S,9R,10S,11S,13S,14S,16R,17R)-17-acetyloxy-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carboxylic acid
• CAS: 101916-26-1
• 化学式: C₂₃H₂₈F₂O₆
• 分子量: 438.469
• InChiKey: QCKUMXDGZMICSW-ALXNQJNESA-N

物化性质

• 沸点：
  568.3±50.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  17α-acetoxy-6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid 在 TEA 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid 17,20-(1'-methyl-1'-methoxy)methylene ketal
  参考文献：
  名称：

  Thiol esters from steroid 17.beta.-carboxylic acids: carboxylate activation and internal participation by 17.alpha.-acylates

  摘要：

  DOI：

  10.1021/jo00362a028
• 作为产物：
  描述：

  二氟拉松 在 过碘酸 、 三乙胺 、 二异丙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 生成 17α-acetoxy-6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid
  参考文献：
  名称：

  Thiol esters from steroid 17.beta.-carboxylic acids: carboxylate activation and internal participation by 17.alpha.-acylates

  摘要：

  DOI：

  10.1021/jo00362a028

文献信息

• Method for the preparation of fluticasone and related 17beta-carbothioic esters using a novel carbothioic acid synthesis and novel purification methods
  申请人：——

  公开号：US20020133032A1

  公开（公告）日：2002-09-19

  This invention discloses a novel method for the conversion of carboxylic acids to carbothioic acids and application of the method to the preparation of androstane carbothiolates, such as fluticasone propionate, which avoids column chromatography.

  本发明揭示了一种将羧酸转化为羧硫酸的新方法，并将该方法应用于制备类固醇类羧硫酸盐，如丙酸氟替卡松，避免了柱层析的方法。
• METHOD FOR THE PREPARATION OF CARBOTHIOIC ACIDS
  申请人：Abbott Laboratories

  公开号：EP1257531B1

  公开（公告）日：2004-09-15
• US7214807B2
  申请人：——

  公开号：US7214807B2

  公开（公告）日：2007-05-08
• [EN] 17.BETA.-FLUOROMETHOXYCARBONYL-ANDROST-4-EN-3-ONE COMPOUNDS WITH A 17.ALPHA.-CARBONATE SUBSTITUENT<br/>[FR] 17.BETA.-FLUOROMETHOXYCARBONYL-ANDROST-4-EN-3-ONE COMPOUNDS WITH A 17.ALPHA.-CARBONATE SUBSTITUENT
  申请人：GLAXO GROUP LTD

  公开号：WO2007057152A1

  公开（公告）日：2007-05-24

  [EN] The present invention is directed to compounds of formula (I) wherein R₁ represents C₄-C₇ branched chain alkyl, C₃-C₈ cycloalkyl optionally substituted by one or more groups independently selected from C₁-C₃ alkyl and methoxy, C₄-C₆ cycloalkylmethyl wherein the methyl group is optionally substituted by a group selected from methyl or ethyl, or a bicycloalkyl group optionally substituted by one or more methyl groups; R₂ represents hydrogen, a methyl group, which may be in either the a or ß configuration, or a methylene group; R₃ and R₄ are the same or a different group and each independently represents hydrogen, halogen or a methyl group; and formula (II) represents a single or a double bond; physiologically acceptable solvates thereof, pharmaceutical compositions comprising the compounds, the use of the compounds for the manufacture of medicaments particularly for the treatment of inflammatory and/or allergic conditions, processes for the preparation of the compounds, and chemical intermediates in the processes for the manufacture of the compounds.
  [FR] The present invention is directed to compounds of formula (I) wherein R₁ represents C₄-C₇ branched chain alkyl, C₃-C₈ cycloalkyl optionally substituted by one or more groups independently selected from C₁-C₃ alkyl and methoxy, C₄-C₆ cycloalkylmethyl wherein the methyl group is optionally substituted by a group selected from methyl or ethyl, or a bicycloalkyl group optionally substituted by one or more methyl groups; R₂ represents hydrogen, a methyl group, which may be in either the a or ß configuration, or a methylene group; R₃ and R₄ are the same or a different group and each independently represents hydrogen, halogen or a methyl group; and formula (II) represents a single or a double bond; physiologically acceptable solvates thereof, pharmaceutical compositions comprising the compounds, the use of the compounds for the manufacture of medicaments particularly for the treatment of inflammatory and/or allergic conditions, processes for the preparation of the compounds, and chemical intermediates in the processes for the manufacture of the compounds.