methyl (E)-3-[1-(dimethylsulfamoyl)-5-(3-methylbut-2-enyl)imidazol-4-yl]prop-2-enoate | 213179-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl (E)-3-[1-(dimethylsulfamoyl)-5-(3-methylbut-2-enyl)imidazol-4-yl]prop-2-enoate
• CAS: 213179-99-8
• 化学式: C₁₄H₂₁N₃O₄S
• 分子量: 327.404
• InChiKey: WYHVPEBCQTURMR-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  89.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-[1-(dimethylsulfamoyl)-5-(3-methylbut-2-enyl)imidazol-4-yl]prop-2-enoate 在 溶剂黄146 作用下， 反应 1.0h， 以96%的产率得到(E)-3-[5-(3-Methyl-but-2-enyl)-1H-imidazol-4-yl]-acrylic acid methyl ester
  参考文献：
  名称：

  First total synthesis of fungerin an antifungal alkaloid from Fusarium sp.

  摘要：

  The First total synthesis of fungerin 1, anew antifungal alkaloid, is described.Starting from a 4,5-diiodoimidazole derivative, the procedure involves regioselective prenylation and Heck type reaction steps to give 1 in high yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01203-9
• 作为产物：
  描述：

  N,N-二甲基-4,5-二碘-1H-咪唑-1-磺酰胺 在 palladium diacetate 乙基溴化镁 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.75h， 生成 methyl (E)-3-[1-(dimethylsulfamoyl)-5-(3-methylbut-2-enyl)imidazol-4-yl]prop-2-enoate
  参考文献：
  名称：

  Design and novel synthesis of aryl-heteroaryl-imidazole MAP kinase inhibitors

  摘要：

  Inhibitors of the MAP kinase p38, potentially useful for the treatment of rheumatoid arthritis and inflammatory diseases, were found to exhibit antifungal activity. We have developed a new diversity-oriented strategy leading to concise and efficient syntheses of known and new members of this compound class. The strategy is based on carbon-carbon cross-coupling reactions using N-protected 4,5-diiodo-irrtidazoles as the starting templates. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01834-3

文献信息

• Design and novel synthesis of aryl-heteroaryl-imidazole MAP kinase inhibitors
  作者：Markus R Dobler

  DOI：10.1016/s0040-4039(03)01834-3

  日期：2003.9

  Inhibitors of the MAP kinase p38, potentially useful for the treatment of rheumatoid arthritis and inflammatory diseases, were found to exhibit antifungal activity. We have developed a new diversity-oriented strategy leading to concise and efficient syntheses of known and new members of this compound class. The strategy is based on carbon-carbon cross-coupling reactions using N-protected 4,5-diiodo-irrtidazoles as the starting templates. (C) 2003 Elsevier Ltd. All rights reserved.
• First total synthesis of fungerin an antifungal alkaloid from Fusarium sp.
  作者：Rachid Benhida、Ruth Lezama、Jean-Louis Fourrey

  DOI：10.1016/s0040-4039(98)01203-9

  日期：1998.8

  The First total synthesis of fungerin 1, anew antifungal alkaloid, is described.Starting from a 4,5-diiodoimidazole derivative, the procedure involves regioselective prenylation and Heck type reaction steps to give 1 in high yield. (C) 1998 Elsevier Science Ltd. All rights reserved.