N-(Benzyloxycarbonyl)-4-(4-pyridyl)-3-fluoroaniline | 166758-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(Benzyloxycarbonyl)-4-(4-pyridyl)-3-fluoroaniline
• 英文别名: benzyl N-(3-fluoro-4-pyridin-4-ylphenyl)carbamate
• CAS: 166758-27-6
• 化学式: C₁₉H₁₅FN₂O₂
• 分子量: 322.339
• InChiKey: QGZBATKGIJWMNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(Benzyloxycarbonyl)-4-(4-pyridyl)-3-fluoroaniline 在 吡啶 、 碘 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 2.33h， 生成 (+/-)-5-(Iodomethyl)-3-<4-(4-pyridyl)-3-fluorophenyl>-2-oxazolidinone
  参考文献：
  名称：

  Regioselective Metalation of Fluoroanilines. An Application to the Synthesis of Fluorinated Oxazolidinone Antibacterial Agents

  摘要：

  The regioselective para lithiation of 3-fluoro- and 3,5-dinuoroaniline stabase derivatives is described. These intermediates were subjected to a reaction sequence involving (1) transmetalation with zinc chloride, (2) a palladium-catalyzed coupling reaction with various pyridyl bromides, and (3) removal of the stabase protecting group, to generate fluorinated 4-(pyridyl)anilines. These compounds are. key subunits for the synthesis of selected fluorinated oxazolidinone antibacterial agents. Representative applications of these intermediates to the synthesis of three potent oxazolidinone analogues are discussed. One facet of the described procedure involves a unique iodocyclocarbamation reaction featuring a pyridine additive.

  DOI：

  10.1021/jo00121a050
• 作为产物：
  描述：

  1-(3-fluorophenyl)-2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane 在 四(三苯基膦)钯 盐酸 、 仲丁基锂 、 potassium carbonate 、 zinc(II) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 22.5h， 生成 N-(Benzyloxycarbonyl)-4-(4-pyridyl)-3-fluoroaniline
  参考文献：
  名称：

  Regioselective Metalation of Fluoroanilines. An Application to the Synthesis of Fluorinated Oxazolidinone Antibacterial Agents

  摘要：

  The regioselective para lithiation of 3-fluoro- and 3,5-dinuoroaniline stabase derivatives is described. These intermediates were subjected to a reaction sequence involving (1) transmetalation with zinc chloride, (2) a palladium-catalyzed coupling reaction with various pyridyl bromides, and (3) removal of the stabase protecting group, to generate fluorinated 4-(pyridyl)anilines. These compounds are. key subunits for the synthesis of selected fluorinated oxazolidinone antibacterial agents. Representative applications of these intermediates to the synthesis of three potent oxazolidinone analogues are discussed. One facet of the described procedure involves a unique iodocyclocarbamation reaction featuring a pyridine additive.

  DOI：

  10.1021/jo00121a050

文献信息

• Regioselective Metalation of Fluoroanilines. An Application to the Synthesis of Fluorinated Oxazolidinone Antibacterial Agents
  作者：Kevin C. Grega、Michael R. Barbachyn、Steven J. Brickner、Stephen A. Mizsak

  DOI：10.1021/jo00121a050

  日期：1995.8

  The regioselective para lithiation of 3-fluoro- and 3,5-dinuoroaniline stabase derivatives is described. These intermediates were subjected to a reaction sequence involving (1) transmetalation with zinc chloride, (2) a palladium-catalyzed coupling reaction with various pyridyl bromides, and (3) removal of the stabase protecting group, to generate fluorinated 4-(pyridyl)anilines. These compounds are. key subunits for the synthesis of selected fluorinated oxazolidinone antibacterial agents. Representative applications of these intermediates to the synthesis of three potent oxazolidinone analogues are discussed. One facet of the described procedure involves a unique iodocyclocarbamation reaction featuring a pyridine additive.