(Z)-1-benzyloxymethyl-4,5-dibromopyrrole-2-carboxylic acid [2-(1-benzyloxymethyl-2-methylsulfanylimidazol-4-yl)-vinyl]amide | 930304-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (Z)-1-benzyloxymethyl-4,5-dibromopyrrole-2-carboxylic acid [2-(1-benzyloxymethyl-2-methylsulfanylimidazol-4-yl)-vinyl]amide
• 英文别名: 1-benzyloxymethyl-4,5-dibromopyrrole-2-carboxylic acid [2-(1-benzyloxymethyl-2-methylsulfanylimidazol-4-yl)-vinyl]amide；4,5-dibromo-N-[(Z)-2-[2-methylsulfanyl-1-(phenylmethoxymethyl)imidazol-4-yl]ethenyl]-1-(phenylmethoxymethyl)pyrrole-2-carboxamide
• CAS: 930304-10-2
• 化学式: C₂₇H₂₆Br₂N₄O₃S
• 分子量: 646.402
• InChiKey: SXDHUBPSUMQDDS-SEYXRHQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  95.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-1-benzyloxymethyl-4,5-dibromopyrrole-2-carboxylic acid [2-(1-benzyloxymethyl-2-methylsulfanylimidazol-4-yl)-vinyl]amide 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以82%的产率得到1-benzyloxymethyl-4,5-dibromopyrrole-2-carbothioic acid [2-(1-benzyloxymethyl-2-methylsulfanylimidazol-4-yl)-vinyl]amide
  参考文献：
  名称：

  A New Total Synthesis of the Zinc Matrixmetalloproteinase Inhibitor Ageladine A Featuring a Biogenetically Patterned 6π-2-Azatriene Electrocyclization

  摘要：

  A convergent second generation total synthesis of the heterocyclic marine sponge metabolite ageladine A has been achieved by using a biomimetically inspired 6 pi 2-azatriene electrocyclization as the key step for formation of the imidazolopyridine moiety.

  DOI：

  10.1021/ol063038a
• 作为产物：
  描述：

  1-benzyloxymethylpyrrole-2-carboxylic acid amide 在 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 caesium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 17.5h， 生成 (Z)-1-benzyloxymethyl-4,5-dibromopyrrole-2-carboxylic acid [2-(1-benzyloxymethyl-2-methylsulfanylimidazol-4-yl)-vinyl]amide
  参考文献：
  名称：

  A New Total Synthesis of the Zinc Matrixmetalloproteinase Inhibitor Ageladine A Featuring a Biogenetically Patterned 6π-2-Azatriene Electrocyclization

  摘要：

  A convergent second generation total synthesis of the heterocyclic marine sponge metabolite ageladine A has been achieved by using a biomimetically inspired 6 pi 2-azatriene electrocyclization as the key step for formation of the imidazolopyridine moiety.

  DOI：

  10.1021/ol063038a

文献信息

• A New Total Synthesis of the Zinc Matrixmetalloproteinase Inhibitor Ageladine A Featuring a Biogenetically Patterned 6π-2-Azatriene Electrocyclization
  作者：Matthew L. Meketa、Steven M. Weinreb

  DOI：10.1021/ol063038a

  日期：2007.3.1

  A convergent second generation total synthesis of the heterocyclic marine sponge metabolite ageladine A has been achieved by using a biomimetically inspired 6 pi 2-azatriene electrocyclization as the key step for formation of the imidazolopyridine moiety.
• A convergent total synthesis of the marine sponge alkaloid ageladine A via a strategic 6π-2-azatriene electrocyclization
  作者：Matthew L. Meketa、Steven M. Weinreb

  DOI：10.1016/j.tet.2007.06.089

  日期：2007.9

  A second generation total synthesis of the marine sponge metabolite ageladine A utilizing a biogenetically inspired 6 pi-2-azaelectrocyclization of triene 34 as the key step is performed to construct the imidazopyridine core of the metabolite. (c) 2007 Elsevier Ltd. All rights reserved.