(4-{(1S,5R,6R)-6-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-3-aza-bicyclo[3.1.0]hex-3-yl}-3-fluoro-phenyl)-carbamic acid benzyl ester | 392660-11-6

• 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: (4-{(1S,5R,6R)-6-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-3-aza-bicyclo[3.1.0]hex-3-yl}-3-fluoro-phenyl)-carbamic acid benzyl ester
• CAS: 392660-11-6
• 化学式: C₂₆H₃₂FN₃O₄
• 分子量: 469.556
• InChiKey: DSBIGLVGMQFKMW-MZADTFQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  71.11
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4-{(1S,5R,6R)-6-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-3-aza-bicyclo[3.1.0]hex-3-yl}-3-fluoro-phenyl)-carbamic acid benzyl ester 在 palladium on activated charcoal 正丁基锂 、 sodium azide 、 TEA 、 氢气 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， -78.0~80.0 ℃ 、379.21 kPa 条件下， 反应 1.5h， 生成 (S)-N-[[3-[3-fluoro-4-[3-(1α,5α,6α)-6-[(N-methyl)aminomethyl]-3-azabicyclo-[3.1.0]hexane]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide
  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：

  tert-Butyl N-[[(1S,5R)-3-azabicyclo[3.1.0]hexan-6-yl]methyl]carbamate 在 palladium on activated charcoal 氢气 、 四丁基碘化铵 、 sodium hydride 、 碳酸氢钠 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 80.0 ℃ 、379.21 kPa 条件下， 生成 (4-{(1S,5R,6R)-6-[(tert-Butoxycarbonyl-methyl-amino)-methyl]-3-aza-bicyclo[3.1.0]hex-3-yl}-3-fluoro-phenyl)-carbamic acid benzyl 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