[1-(2-nitrophenyl)-1H-pyrrol-2-ylsulfanyl]acetonitrile | 87574-19-4

• 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-(2-nitrophenyl)-1H-pyrrol-2-ylsulfanyl]acetonitrile
• 英文别名: 2-[1-(2-Nitrophenyl)pyrrol-2-yl]sulfanylacetonitrile
• CAS: 87574-19-4
• 化学式: C₁₂H₉N₃O₂S
• 分子量: 259.288
• InChiKey: NUCQWHMELCDFRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  99.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [1-(2-nitrophenyl)-1H-pyrrol-2-ylsulfanyl]acetonitrile 在 palladium on activated charcoal sodium hydroxide 、 sodium tetrahydroborate 、 盐酸 作用下， 以 1,4-二氧六环 、 水 、 乙醇 为溶剂， 反应 0.33h， 以43%的产率得到6-amino-5H-pyrrolo[1,2-a][3.1.6]benzothiadiazocin-7-oxide
  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 、 氯乙腈 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以62%的产率得到[1-(2-nitrophenyl)-1H-pyrrol-2-ylsulfanyl]acetonitrile
  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

• Cheeseman, G. W. H.; Hawi, A. A., Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 591 - 594
  作者：Cheeseman, G. W. H.、Hawi, A. A.

  DOI：——

  日期：——
• CHEESEMAN, G. W. H.;HAWI, A. A., J. HETEROCYCL. CHEM., 1983, 20, N 3, 591-593
  作者：CHEESEMAN, G. W. H.、HAWI, A. A.

  DOI：——

  日期：——
• 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.