3β-N-[hydroxypentyl]amino-4-cholestene | 1030296-34-4

• 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: 3β-N-[hydroxypentyl]amino-4-cholestene
• 英文别名: 5-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]amino]pentan-1-ol
• CAS: 1030296-34-4
• 化学式: C₃₂H₅₇NO
• 分子量: 471.811
• InChiKey: BIYLQLZQFRASAW-RWFZIKKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-氨基-1-戊醇 、 4-胆甾烯-3-酮 在 titanium(IV) isopropylate 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 14.0h， 以53%的产率得到3β-N-[hydroxypentyl]amino-4-cholestene
  参考文献：
  名称：

  Efficient preparation of secondary aminoalcohols through a Ti(IV) reductive amination procedure. Application to the synthesis and antibacterial evaluation of new 3β-N-[hydroxyalkyl]aminosteroid derivatives

  摘要：

  An efficient method for the synthesis of various secondary aminoalcohols through a titanium(IV) isopropoxide-mediated reductive amination reaction of ketones is reported. Thus, different ketones gave the expected products in moderate to excellent yields up to 89% in numerous cases. A series of 3 beta-N-[hydroxyalkyl]aminosteroid derivatives were prepared according to this methodology and evaluated for their in vitro antimicrobial properties against human pathogens. All the compounds showed moderate to excellent activities against Gram-positive bacteria exhibiting similar results against Staphylococcus aureus and Streptococcus faecalis with Minimum Inhibitory Concentrations (MICs) varying from 3.12 to 25 mu g/mL. No significant antibacterial activities are encountered against Gram-negative bacteria. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.055

文献信息

• Efficient preparation of secondary aminoalcohols through a Ti(IV) reductive amination procedure. Application to the synthesis and antibacterial evaluation of new 3β-N-[hydroxyalkyl]aminosteroid derivatives
  作者：Chanaz Salmi、Céline Loncle、Yves Letourneux、Jean Michel Brunel

  DOI：10.1016/j.tet.2008.02.055

  日期：2008.5

  An efficient method for the synthesis of various secondary aminoalcohols through a titanium(IV) isopropoxide-mediated reductive amination reaction of ketones is reported. Thus, different ketones gave the expected products in moderate to excellent yields up to 89% in numerous cases. A series of 3 beta-N-[hydroxyalkyl]aminosteroid derivatives were prepared according to this methodology and evaluated for their in vitro antimicrobial properties against human pathogens. All the compounds showed moderate to excellent activities against Gram-positive bacteria exhibiting similar results against Staphylococcus aureus and Streptococcus faecalis with Minimum Inhibitory Concentrations (MICs) varying from 3.12 to 25 mu g/mL. No significant antibacterial activities are encountered against Gram-negative bacteria. (c) 2008 Elsevier Ltd. All rights reserved.