((S)-9-Fluoro-5-methyl-1,2,3,3a,4,5-hexahydro-pyrrolo[1,2-a]quinoxalin-7-yl)-carbamic acid benzyl ester | 909020-18-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: ((S)-9-Fluoro-5-methyl-1,2,3,3a,4,5-hexahydro-pyrrolo[1,2-a]quinoxalin-7-yl)-carbamic acid benzyl ester
• CAS: 909020-18-4
• 化学式: C₂₀H₂₂FN₃O₂
• 分子量: 355.412
• InChiKey: AUNGBNWFAWYKKM-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  44.81
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ((S)-9-Fluoro-5-methyl-1,2,3,3a,4,5-hexahydro-pyrrolo[1,2-a]quinoxalin-7-yl)-carbamic acid benzyl ester 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 Methanesulfonic acid (R)-3-((S)-9-fluoro-5-methyl-1,2,3,3a,4,5-hexahydro-pyrrolo[1,2-a]quinoxalin-7-yl)-2-oxo-oxazolidin-5-ylmethyl ester
  参考文献：
  名称：

  Synthesis of novel tricyclic oxazolidinones by a tandem SN2 and SNAr reaction: SAR studies on conformationally constrained analogues of Linezolid

  摘要：

  A series of conformationally constrained analogues of Linezolid were synthesised by employing a tandem SN2 and SNAr reaction as the key step and tested for antibacterial activity. While the hexahydroazolo-quinoxaline compounds were inactive, the tetrahydroazolo-benzothiazine compounds exhibited interesting antibacterial activity. The introduction of fluorine in the aromatic ring further made the compounds more potent in acetamide compounds resulting in an interesting analogue 32. However, the introduction of fluorine (analogue 34) on the already potent non-fluorine thiocarbamate 21 did not have any influence on the activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.071
• 作为产物：
  描述：

  (S)-2-Bromomethyl-1-(2,6-difluoro-4-nitro-phenyl)-pyrrolidine 在 盐酸 、 氢氧化钾 、 铁粉 、 sodium carbonate 作用下， 以 乙醇 、 二甲基亚砜 、 丙酮 为溶剂， 反应 5.75h， 生成 ((S)-9-Fluoro-5-methyl-1,2,3,3a,4,5-hexahydro-pyrrolo[1,2-a]quinoxalin-7-yl)-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis of novel tricyclic oxazolidinones by a tandem SN2 and SNAr reaction: SAR studies on conformationally constrained analogues of Linezolid

  摘要：

  A series of conformationally constrained analogues of Linezolid were synthesised by employing a tandem SN2 and SNAr reaction as the key step and tested for antibacterial activity. While the hexahydroazolo-quinoxaline compounds were inactive, the tetrahydroazolo-benzothiazine compounds exhibited interesting antibacterial activity. The introduction of fluorine in the aromatic ring further made the compounds more potent in acetamide compounds resulting in an interesting analogue 32. However, the introduction of fluorine (analogue 34) on the already potent non-fluorine thiocarbamate 21 did not have any influence on the activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.05.071