9α-chloro-6α-fluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioic acid, S-(iodomethyl) ester | 785806-95-3

• 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: 9α-chloro-6α-fluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioic acid, S-(iodomethyl) ester
• CAS: 785806-95-3
• 化学式: C₂₇H₂₉ClFIO₆S
• 分子量: 662.946
• InChiKey: FIQKVZJHYLTGTF-VLSRWLAYSA-N

物化性质

• 沸点：
  689.5±55.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.66
• 重原子数：
  37.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  93.81
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  9α-chloro-6α-fluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioic acid, S-(iodomethyl) ester 在 silver fluoride 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以35%的产率得到氟替卡松杂质
  参考文献：
  名称：

  Synthesis and biological properties of novel glucocorticoid androstene C-17 furoate esters

  摘要：

  A series of novel corticosteroid derivatives featuring C-17 furoate ester functionality have been synthesised. Profiling in vitro and in vivo has resulted in the identification of a compound with a longer duration of action and a lower oral side effect profile in rodents compared to budesonide. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.027
• 作为产物：
  描述：

  Furan-2-carboxylic acid (6S,8S,9R,10S,11S,13S,14S,16R,17R)-9-chloro-6-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-thiocarboxy-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester 在 碳酸氢钠 、 sodium iodide 作用下， 以 N,N-二甲基乙酰胺 、 丙酮 为溶剂， 反应 8.0h， 生成 9α-chloro-6α-fluoro-17α-[(2-furanylcarbonyl)oxy]-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioic acid, S-(iodomethyl) ester
  参考文献：
  名称：

  Synthesis and biological properties of novel glucocorticoid androstene C-17 furoate esters

  摘要：

  A series of novel corticosteroid derivatives featuring C-17 furoate ester functionality have been synthesised. Profiling in vitro and in vivo has resulted in the identification of a compound with a longer duration of action and a lower oral side effect profile in rodents compared to budesonide. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.06.027