diethyl (1-butyl-5-methyl-2-phenyl-1H-pyrrol-3-yl)phosphonate | 1606985-94-7

• 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 (1-butyl-5-methyl-2-phenyl-1H-pyrrol-3-yl)phosphonate
• 英文别名: 1-Butyl-3-[diethoxy(oxido)phosphaniumyl]-5-methyl-2-phenylpyrrole；1-butyl-3-[diethoxy(oxido)phosphaniumyl]-5-methyl-2-phenylpyrrole
• CAS: 1606985-94-7
• 化学式: C₁₉H₂₈NO₃P
• 分子量: 349.41
• InChiKey: OAHAOIXKOUXIQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  46.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  diethyl (1-butyl-5-methyl-2-phenyl-1H-pyrrol-3-yl)phosphonate 在 N-溴代丁二酰亚胺(NBS) 、 仲丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 1.5h， 生成 diethyl (1-butyl-4,5-dimethyl-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
• 作为产物：
  描述：

  diethyl (1-(butylamino)-1-phenylpent-1-en-4-yn-2-yl)phosphonate 在 乙腈 、 zinc(II) chloride 作用下， 反应 20.0h， 以94%的产率得到diethyl (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

文献信息

• Preparation of Tetrasubstituted 3-Phosphonopyrroles through Hydroamination: Scope and Limitations
  作者：Wouter Debrouwer、Thomas S. A. Heugebaert、Christian V. Stevens

  DOI：10.1021/jo500139z

  日期：2014.5.16

  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.