{1-[2-Fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidin-4-yl}-methyl-carbamic acid tert-butyl ester | 392660-22-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环丁烷
• 英文名称: {1-[2-Fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidin-4-yl}-methyl-carbamic acid tert-butyl ester
• CAS: 392660-22-9
• 化学式: C₂₁H₃₀FN₃O₅
• 分子量: 423.485
• InChiKey: ZGLYBQPGFONWDI-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  82.55
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  {1-[2-Fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidin-4-yl}-methyl-carbamic acid tert-butyl ester 在 palladium on activated charcoal sodium azide 、 TEA 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、379.21 kPa 条件下， 生成 (1-{4-[(S)-5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenyl}-piperidin-4-yl)-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：

  [1-(4-Amino-2-fluoro-phenyl)-piperidin-4-yl]-methyl-carbamic acid tert-butyl ester 在 正丁基锂 、 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 {1-[2-Fluoro-4-((R)-5-hydroxymethyl-2-oxo-oxazolidin-3-yl)-phenyl]-piperidin-4-yl}-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