2-(3'-isopropoxy-4'-methoxyphenyl)-6-methoxy-3-(3'',4'',5''-trimethoxyphenyl)benzo[b]thiophene | 334708-25-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 2-(3'-isopropoxy-4'-methoxyphenyl)-6-methoxy-3-(3'',4'',5''-trimethoxyphenyl)benzo[b]thiophene
• 英文别名: 6-Methoxy-2-(4-methoxy-3-propan-2-yloxyphenyl)-3-(3,4,5-trimethoxyphenyl)-1-benzothiophene
• CAS: 334708-25-7
• 化学式: C₂₈H₃₀O₆S
• 分子量: 494.609
• InChiKey: OLNCJADVAVYPCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(3'-isopropoxy-4'-methoxyphenyl)-6-methoxy-3-(3'',4'',5''-trimethoxyphenyl)benzo[b]thiophene 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以97%的产率得到2-(3'-hydroxy-4'-methoxyphenyl)-6-methoxy-3-(3'',4'',5''-trimethoxyphenyl)benzo[b]thiophene
  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：

  benzyl 2-iodo-5-methoxyphenyl sulfide 在 正丁基锂 、 碘 、 叔丁基锂 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 18.33h， 生成 2-(3'-isopropoxy-4'-methoxyphenyl)-6-methoxy-3-(3'',4'',5''-trimethoxyphenyl)benzo[b]thiophene
  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

文献信息

• A Novel Palladium-Mediated Coupling Approach to 2,3-Disubstituted Benzo[<i>b</i>]thiophenes and Its Application to the Synthesis of Tubulin Binding Agents
  作者：Bernard L. Flynn、Pascal Verdier-Pinard、Ernest Hamel

  DOI：10.1021/ol0067179

  日期：2001.3.1

  [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.