diethyl (4-bromo-1-butyl-5-methyl-2-phenyl-1H-pyrrol-3-yl)-phosphonate | 1606986-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: diethyl (4-bromo-1-butyl-5-methyl-2-phenyl-1H-pyrrol-3-yl)-phosphonate
• CAS: 1606986-05-3
• 化学式: C₁₉H₂₇BrNO₃P
• 分子量: 428.306
• InChiKey: ICYMVNLAIHRCGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.92
• 重原子数：
  25.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  40.46
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  diethyl (4-bromo-1-butyl-5-methyl-2-phenyl-1H-pyrrol-3-yl)-phosphonate 在 仲丁基锂 、 重水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以57%的产率得到diethyl (1-butyl-5-methyl-2-phenyl-1H-pyrrol-3-yl-4-d)phosphonate
  参考文献：
  名称：

  Preparation of Tetrasubstituted 3-Phosphonopyrroles through Hydroamination: Scope and Limitations

  摘要：

  Phosphonylated pyrroles were obtained by a ZnCl2-catalyzed 5-exo-dig hydroamination of propargylic enamines. These starting compounds were obtained in two steps from commercially available beta-ketophosphonates. The method tolerates a wide variety of substituents at the 1,2- and 5-position of the pyrrole, while further derivatization allows for the introduction of substituents at the 4-position via lithiation or halogenation.

  DOI：

  10.1021/jo500139z
• 作为产物：
  描述：

  diethyl (1-(butylamino)-1-phenylpent-1-en-4-yn-2-yl)phosphonate 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 乙腈 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.5h， 生成 diethyl (4-bromo-1-butyl-5-methyl-2-phenyl-1H-pyrrol-3-yl)-phosphonate
  参考文献：
  名称：

  Preparation of Tetrasubstituted 3-Phosphonopyrroles through Hydroamination: Scope and Limitations

  摘要：

  Phosphonylated pyrroles were obtained by a ZnCl2-catalyzed 5-exo-dig hydroamination of propargylic enamines. These starting compounds were obtained in two steps from commercially available beta-ketophosphonates. The method tolerates a wide variety of substituents at the 1,2- and 5-position of the pyrrole, while further derivatization allows for the introduction of substituents at the 4-position via lithiation or halogenation.

  DOI：

  10.1021/jo500139z