2-Benzylsulfanyl-4-methoxy-1-(4-methoxy-phenylethynyl)-benzene | 1025928-71-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-Benzylsulfanyl-4-methoxy-1-(4-methoxy-phenylethynyl)-benzene
• 英文别名: 2-Benzylsulfanyl-4-methoxy-1-[2-(4-methoxyphenyl)ethynyl]benzene
• CAS: 1025928-71-5
• 化学式: C₂₃H₂₀O₂S
• 分子量: 360.477
• InChiKey: HTFKXJIICUQCAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Benzylsulfanyl-4-methoxy-1-(4-methoxy-phenylethynyl)-benzene 在 碘 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到3-iodo-6-methoxy-2-(4-methoxyphenyl)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：

  dithiocarbonic acid O-ethyl ester S-(2-iodo-5-methoxyphenyl) 在 氢氧化钾 、 正丁基锂 、 四丁基硫酸氢铵 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 2-Benzylsulfanyl-4-methoxy-1-(4-methoxy-phenylethynyl)-benzene
  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.