7β-fluoro-22-hydroxy-23,24-bisnor-5α-cholan-3-one | 952305-44-1

• 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: 7β-fluoro-22-hydroxy-23,24-bisnor-5α-cholan-3-one
• CAS: 952305-44-1
• 化学式: C₂₂H₃₅FO₂
• 分子量: 350.517
• InChiKey: CXOVQORRWZFHPB-DKMLOXBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.79
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  7β-fluoro-22-hydroxy-23,24-bisnor-5α-cholan-3-one 在 甲醇 、 氯化亚砜 、 pyridine-SO3 complex 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Synthesis and antimicrobial activity of 7-fluoro-3-aminosteroids

  摘要：

  A series of 7-fluoro-3-aminosteroids were synthesized and their in vitro antimicrobial activities were evaluated against Gram-positive and Gram-negative bacteria. The nucleophilic fluorination of several 7 beta-hydroxysteroids by diethylaminosulfur trifluoride in n-pentane, followed by reductive amination of the resulting 7-fluoro-3-ketosteroids with spermidine in the presence of NaBH3CN, afforded 7-fluoro-3-aminosteroids in high yield. Compound 25 showed the highest antimicrobial activity against Staphylococcus aureus, Pseudomonas aeruginosa, Streptococcus pyogenes, and Escherichia coli. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.001
• 作为产物：
  描述：

  3-dioxolane-22-tert-butyldimethylsilyloxy-23,24-bisnorchola-5-en-7-one 在 乙醇 、 二乙胺基三氟化硫 、 lithium 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 氨 、 丙酮 、 正戊烷 为溶剂， 反应 7.5h， 生成 7β-fluoro-22-hydroxy-23,24-bisnor-5α-cholan-3-one
  参考文献：
  名称：

  Synthesis and antimicrobial activity of 7-fluoro-3-aminosteroids

  摘要：

  A series of 7-fluoro-3-aminosteroids were synthesized and their in vitro antimicrobial activities were evaluated against Gram-positive and Gram-negative bacteria. The nucleophilic fluorination of several 7 beta-hydroxysteroids by diethylaminosulfur trifluoride in n-pentane, followed by reductive amination of the resulting 7-fluoro-3-ketosteroids with spermidine in the presence of NaBH3CN, afforded 7-fluoro-3-aminosteroids in high yield. Compound 25 showed the highest antimicrobial activity against Staphylococcus aureus, Pseudomonas aeruginosa, Streptococcus pyogenes, and Escherichia coli. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.001