diethyl 5-acetyl-1-methyl-1H-pyrrol-2-ylphosphonate | 1394991-86-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: diethyl 5-acetyl-1-methyl-1H-pyrrol-2-ylphosphonate
• 英文别名: 1-(5-Diethoxyphosphoryl-1-methylpyrrol-2-yl)ethanone；1-(5-diethoxyphosphoryl-1-methylpyrrol-2-yl)ethanone
• CAS: 1394991-86-6
• 化学式: C₁₁H₁₈NO₄P
• 分子量: 259.242
• InChiKey: ADFPPBBFPKIUAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-乙酰基-1-甲基吡咯 、 亚磷酸二乙酯 在 dipotassium peroxodisulfate 、 silver nitrate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 10.0h， 以85%的产率得到diethyl 5-acetyl-1-methyl-1H-pyrrol-2-ylphosphonate
  参考文献：
  名称：

  Coupling Reactions of Heteroarenes with Phosphites under Silver Catalysis

  摘要：

  A silver-catalyzed dehydrogenative cross-coupling reaction of substituted furans, thiophene, thioazole, and pyrrole 1a-e with dialkyl phosphites 2 was first developed to afford corresponding phosphonated products 3a-h with up to 89% yield and good regioselectivities. Moreover, an unprecedented coupling of various substituted pyridines 1f-k with dialkyl phosphites 2 using AgNO3 as a catalyst and K2S2O8 as an oxidant, followed by reduction with Na2S2O3, was also realized to furnish desired pyridine phosphonates 3i-q in satisfactory yields with good regioselectivities.

  DOI：

  10.1021/jo301108g

文献信息

• Coupling Reactions of Heteroarenes with Phosphites under Silver Catalysis
  作者：Chang-Bing Xiang、Yong-Jun Bian、Xue-Rong Mao、Zhi-Zhen Huang

  DOI：10.1021/jo301108g

  日期：2012.9.7

  A silver-catalyzed dehydrogenative cross-coupling reaction of substituted furans, thiophene, thioazole, and pyrrole 1a-e with dialkyl phosphites 2 was first developed to afford corresponding phosphonated products 3a-h with up to 89% yield and good regioselectivities. Moreover, an unprecedented coupling of various substituted pyridines 1f-k with dialkyl phosphites 2 using AgNO3 as a catalyst and K2S2O8 as an oxidant, followed by reduction with Na2S2O3, was also realized to furnish desired pyridine phosphonates 3i-q in satisfactory yields with good regioselectivities.