5-{Hydroxy-[6-methoxy-2-(3,4,5-trimethoxy-phenyl)-benzo[b]thiophen-3-yl]-methyl}-2-methoxy-phenol | 334708-29-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-{Hydroxy-[6-methoxy-2-(3,4,5-trimethoxy-phenyl)-benzo[b]thiophen-3-yl]-methyl}-2-methoxy-phenol
• 英文别名: 5-[hydroxy-[6-methoxy-2-(3,4,5-trimethoxyphenyl)-1-benzothiophen-3-yl]methyl]-2-methoxyphenol
• CAS: 334708-29-1
• 化学式: C₂₆H₂₆O₇S
• 分子量: 482.554
• InChiKey: VBWXJYSVCUTWOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-{Hydroxy-[6-methoxy-2-(3,4,5-trimethoxy-phenyl)-benzo[b]thiophen-3-yl]-methyl}-2-methoxy-phenol 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到(3-Hydroxy-4-methoxy-phenyl)-[6-methoxy-2-(3,4,5-trimethoxy-phenyl)-benzo[b]thiophen-3-yl]-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：

  4-溴-3-碘苯甲醚 在 1,1'-双(二苯基膦)二茂铁 、 氢氧化钾 、 正丁基锂 、 碘 、 三乙胺 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 5-{Hydroxy-[6-methoxy-2-(3,4,5-trimethoxy-phenyl)-benzo[b]thiophen-3-yl]-methyl}-2-methoxy-phenol
  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.