[6-(3-Isopropoxy-4-methoxy-phenyl)-thieno[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-yl]-(3,4,5-trimethoxy-phenyl)-methanone | 334708-32-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [6-(3-Isopropoxy-4-methoxy-phenyl)-thieno[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-yl]-(3,4,5-trimethoxy-phenyl)-methanone
• CAS: 334708-32-6
• 化学式: C₂₉H₂₈O₈S
• 分子量: 536.603
• InChiKey: GADCUWRKYYDGFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.35
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  81.68
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  [6-(3-Isopropoxy-4-methoxy-phenyl)-thieno[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-yl]-(3,4,5-trimethoxy-phenyl)-methanone 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到[6-(3-Hydroxy-4-methoxy-phenyl)-thieno[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-yl]-(3,4,5-trimethoxy-phenyl)-methanone
  参考文献：
  名称：

  A Novel Palladium-Mediated Coupling Approach to 2,3-Disubstituted Benzo[b]thiophenes and Its Application to the Synthesis of Tubulin Binding Agents

  摘要：

  [GRAPHICS]Flexible, convergent access to 2,3-disubstituted benzo[b]thiophenes has been developed. The most concise approach involves sequential coupling of o-bromoiodobenzenes with benzylmercaptan and zinc acetylides to give benzyl o-ethynylphenyl sulfides which react with iodine to give 3-iodobenzo[b]thiophenes in a 5-endo-dig iodocyclization. These iodides can be further elaborated using palladium-mediated coupling and/or metalation techniques. This method has been applied to the synthesis of some novel tubulin binding agents.

  DOI：

  10.1021/ol0067179
• 作为产物：
  描述：

  5-bromo-6-iodobenzo[d][1,3]dioxole 在 1,1'-双(二苯基膦)二茂铁 、 正丁基锂 、 碘 、 异丙基氯化镁 、 三乙胺 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 [6-(3-Isopropoxy-4-methoxy-phenyl)-thieno[2',3':4,5]benzo[1,2-d][1,3]dioxol-7-yl]-(3,4,5-trimethoxy-phenyl)-methanone
  参考文献：
  名称：

  A Novel Palladium-Mediated Coupling Approach to 2,3-Disubstituted Benzo[b]thiophenes and Its Application to the Synthesis of Tubulin Binding Agents

  摘要：

  [GRAPHICS]Flexible, convergent access to 2,3-disubstituted benzo[b]thiophenes has been developed. The most concise approach involves sequential coupling of o-bromoiodobenzenes with benzylmercaptan and zinc acetylides to give benzyl o-ethynylphenyl sulfides which react with iodine to give 3-iodobenzo[b]thiophenes in a 5-endo-dig iodocyclization. These iodides can be further elaborated using palladium-mediated coupling and/or metalation techniques. This method has been applied to the synthesis of some novel tubulin binding agents.

  DOI：

  10.1021/ol0067179