3-benzyloxymethyl-4-(1-benzyloxymethyl-4,5-dibromopyrrol-2-yl)-2-methylsulfanylimidazo[4,5-c]pyridine | 930304-13-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 3-benzyloxymethyl-4-(1-benzyloxymethyl-4,5-dibromopyrrol-2-yl)-2-methylsulfanylimidazo[4,5-c]pyridine
• 英文别名: 4-[4,5-Dibromo-1-(phenylmethoxymethyl)pyrrol-2-yl]-2-methylsulfanyl-3-(phenylmethoxymethyl)imidazo[4,5-c]pyridine
• CAS: 930304-13-5
• 化学式: C₂₇H₂₄Br₂N₄O₂S
• 分子量: 628.387
• InChiKey: CKGXSSFEEUWVAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-benzyloxymethyl-4-(1-benzyloxymethyl-4,5-dibromopyrrol-2-yl)-2-methylsulfanylimidazo[4,5-c]pyridine 在 Lindlar's catalyst 三氯化铝 、 氢气 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 25.08h， 生成 阿法拉定A，TFA
  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-benzyloxymethyl-4,5-dibromopyrrole-2-carbothioic acid [2-(1-benzyloxymethyl-2-methylsulfanylimidazol-4-yl)-vinyl]amide 在 均三甲苯 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 3-benzyloxymethyl-4-(1-benzyloxymethyl-4,5-dibromopyrrol-2-yl)-2-methylsulfanylimidazo[4,5-c]pyridine
  参考文献：
  名称：

  A convergent total synthesis of the marine sponge alkaloid ageladine A via a strategic 6π-2-azatriene electrocyclization

  摘要：

  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.

  DOI：

  10.1016/j.tet.2007.06.089

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.