[(1R,5S,6S)-3-(2-Fluoro-4-nitro-phenyl)-3-aza-bicyclo[3.1.0]hex-6-ylmethyl]-carbamic acid tert-butyl ester | 392660-08-1

• 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: [(1R,5S,6S)-3-(2-Fluoro-4-nitro-phenyl)-3-aza-bicyclo[3.1.0]hex-6-ylmethyl]-carbamic acid tert-butyl ester
• CAS: 392660-08-1
• 化学式: C₁₇H₂₂FN₃O₄
• 分子量: 351.378
• InChiKey: YYLBNXLQIZLARY-XYYAHUGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  84.71
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [(1R,5S,6S)-3-(2-Fluoro-4-nitro-phenyl)-3-aza-bicyclo[3.1.0]hex-6-ylmethyl]-carbamic acid tert-butyl ester 在 palladium on activated charcoal 氢气 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 20.0 ℃ 、379.21 kPa 条件下， 生成 [(1S,5R,6R)-3-(4-Amino-2-fluoro-phenyl)-3-aza-bicyclo[3.1.0]hex-6-ylmethyl]-methyl-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and SAR of novel oxazolidinones: Discovery of ranbezolid

  摘要：

  Novel oxazolidinones were synthesized containing a number of substituted five-membered heterocycles attached to the 'piperazinyl-phenyl-oxazolidinone' core of eperezolid. Further, the piperazine ring of the core was replaced by other diamino-heterocycles. These modifications led to several compounds with potent activity against a spectrum of resistant and susceptible Gram-positive organisms, along with the identification of ranbezolid (RBx 7644) as a clinical candidate. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.063
• 作为产物：
  描述：

  3,4-二氟硝基苯 、 tert-Butyl N-[[(1S,5R)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]carbamate 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 生成 [(1R,5S,6S)-3-(2-Fluoro-4-nitro-phenyl)-3-aza-bicyclo[3.1.0]hex-6-ylmethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and SAR of novel oxazolidinones: Discovery of ranbezolid

  摘要：

  Novel oxazolidinones were synthesized containing a number of substituted five-membered heterocycles attached to the 'piperazinyl-phenyl-oxazolidinone' core of eperezolid. Further, the piperazine ring of the core was replaced by other diamino-heterocycles. These modifications led to several compounds with potent activity against a spectrum of resistant and susceptible Gram-positive organisms, along with the identification of ranbezolid (RBx 7644) as a clinical candidate. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.06.063