1-{[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfinyl}acetone | 781661-36-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-{[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfinyl}acetone
• 英文别名: 1-[1-(2-Nitrophenyl)pyrrol-2-yl]sulfinylpropan-2-one；1-[1-(2-nitrophenyl)pyrrol-2-yl]sulfinylpropan-2-one
• CAS: 781661-36-7
• 化学式: C₁₃H₁₂N₂O₄S
• 分子量: 292.315
• InChiKey: ARJOKNLUHKDZGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-{[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfinyl}acetone 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以72%的产率得到1-(2-nitrophenyl)(1H-pyrrol-2-ylsulfinyl)methane
  参考文献：
  名称：

  Novel pyrrolo[1,2-a][3.1.6]benzothiadiazocine ring synthesis. Unusual Truce–Smiles type rearrangement of 1-{[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfonyl(or sulfinyl)}acetone

  摘要：

  Reaction of 1-{[1-(2-nitrophenyl)-1H-pyffol-2-yl]sulfonyl} acetone with sodium hydroxide with or without zinc gave 1-(2-nitrophenyl)(1H-pyrrol-2-ylsulfonyl)methane by a Truce-Smiles type of transformation and 1-(2-nitrophenyl)-2-methylsulfonylpyrrole by deacetylation. Similar treatment of 1-{[1-(2-nitrophenyl)-1H-pyffol-2-yl]sulfinyl}acetone gave only 1-(2-nitro-phenyl)(1H-pyrrol-2-ylsulfinyl)methane. 1-{[1-(2-Nitrophenyl)-1H-pyrrol-2-yl]sulfanyl}acetone, 2-{[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfanyl}-1-phenylethan-1-one or 2-{[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfanyl}acetonitrile were reductively cyclised with sodium borohydride and 5% palladium-on-carbon into 6-methyl(or phenyl)-5,6-dihydro-7H-pyrrolo[1,2-a][3.1.6]benzothiadiazocin-7-ol or 6-amino-5H-pyrrolo[1,2-a][3.1.6]benzothiadiazocine-7-oxide, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.036
• 作为产物：
  描述：

  1-(2-nitrophenyl)-2-thiocyanato-1H-pyrrole 在 sodium hydroxide 、 sodium tetrahydroborate 、 Oxone 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 0.5h， 生成 1-{[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfinyl}acetone
  参考文献：
  名称：

  Novel pyrrolo[1,2-a][3.1.6]benzothiadiazocine ring synthesis. Unusual Truce–Smiles type rearrangement of 1-{[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfonyl(or sulfinyl)}acetone

  摘要：

  Reaction of 1-{[1-(2-nitrophenyl)-1H-pyffol-2-yl]sulfonyl} acetone with sodium hydroxide with or without zinc gave 1-(2-nitrophenyl)(1H-pyrrol-2-ylsulfonyl)methane by a Truce-Smiles type of transformation and 1-(2-nitrophenyl)-2-methylsulfonylpyrrole by deacetylation. Similar treatment of 1-{[1-(2-nitrophenyl)-1H-pyffol-2-yl]sulfinyl}acetone gave only 1-(2-nitro-phenyl)(1H-pyrrol-2-ylsulfinyl)methane. 1-{[1-(2-Nitrophenyl)-1H-pyrrol-2-yl]sulfanyl}acetone, 2-{[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfanyl}-1-phenylethan-1-one or 2-{[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfanyl}acetonitrile were reductively cyclised with sodium borohydride and 5% palladium-on-carbon into 6-methyl(or phenyl)-5,6-dihydro-7H-pyrrolo[1,2-a][3.1.6]benzothiadiazocin-7-ol or 6-amino-5H-pyrrolo[1,2-a][3.1.6]benzothiadiazocine-7-oxide, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.07.036

文献信息

• Novel pyrrolo[1,2-a][3.1.6]benzothiadiazocine ring synthesis. Unusual Truce–Smiles type rearrangement of 1-{[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfonyl(or sulfinyl)}acetone
  作者：Athanasios Kimbaris、Jonathan Cobb、Georgios Tsakonas、George Varvounis

  DOI：10.1016/j.tet.2004.07.036

  日期：2004.9

  Reaction of 1-[1-(2-nitrophenyl)-1H-pyffol-2-yl]sulfonyl} acetone with sodium hydroxide with or without zinc gave 1-(2-nitrophenyl)(1H-pyrrol-2-ylsulfonyl)methane by a Truce-Smiles type of transformation and 1-(2-nitrophenyl)-2-methylsulfonylpyrrole by deacetylation. Similar treatment of 1-[1-(2-nitrophenyl)-1H-pyffol-2-yl]sulfinyl}acetone gave only 1-(2-nitro-phenyl)(1H-pyrrol-2-ylsulfinyl)methane. 1-[1-(2-Nitrophenyl)-1H-pyrrol-2-yl]sulfanyl}acetone, 2-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfanyl}-1-phenylethan-1-one or 2-[1-(2-nitrophenyl)-1H-pyrrol-2-yl]sulfanyl}acetonitrile were reductively cyclised with sodium borohydride and 5% palladium-on-carbon into 6-methyl(or phenyl)-5,6-dihydro-7H-pyrrolo[1,2-a][3.1.6]benzothiadiazocin-7-ol or 6-amino-5H-pyrrolo[1,2-a][3.1.6]benzothiadiazocine-7-oxide, respectively. (C) 2004 Elsevier Ltd. All rights reserved.