Pregnan-3-one, 7-fluoro-21-hydroxy-20-methyl-, (5a,7a,20S)- | 398138-66-4

• 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: Pregnan-3-one, 7-fluoro-21-hydroxy-20-methyl-, (5a,7a,20S)-
• 英文别名: 7α-fluoro-22-hydroxy-23,24-bisnor-5α-cholan-3-one；3-keto-7α-fluoro-23,24-bisnor-5α-chol-22-ol
• CAS: 398138-66-4
• 化学式: C₂₂H₃₅FO₂
• 分子量: 350.517
• InChiKey: CXOVQORRWZFHPB-YJPOZTGBSA-N

物化性质

• 熔点：
  177-178 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  453.4±20.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

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：

  Pregnan-3-one, 7-fluoro-21-hydroxy-20-methyl-, (5a,7a,20S)- 在 甲醇 、 氯化亚砜 、 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 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-bisnor-5α-cholan-7β-ol 在 二乙胺基三氟化硫 、 对甲苯磺酸 作用下， 以 丙酮 、 正戊烷 为溶剂， 反应 6.5h， 生成 Pregnan-3-one, 7-fluoro-21-hydroxy-20-methyl-, (5a,7a,20S)-
  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

文献信息

• Synthesis and antimicrobial activity of new 3α-Hydroxy-23,24-bisnorcholane polyamine carbamates
  作者：Hong-Seok Kim、Kyung-Chan Kwon、Ki Soo Kim、Cheol Hae Lee

  DOI：10.1016/s0960-894x(01)00632-1

  日期：2001.12

  3 alpha -Hydroxy-23,24-bisnorcholane spermidine and spermine carbamates 2-7 have been synthesized and their antimicrobial and hemolytic activities were evaluated. They exhibited excellent in vitro activities especially against methicillin-resistant Staphylococcus aureus. (C) 2001 Elsevier Science Ltd. All rights reserved.