benzyl 2-[2'-(3''-isopropoxy-4''-methoxyphenyl)-ethynyl]-5-methoxyphenyl sulfide | 334708-38-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: benzyl 2-[2'-(3''-isopropoxy-4''-methoxyphenyl)-ethynyl]-5-methoxyphenyl sulfide
• 英文别名: 2-Benzylsulfanyl-4-methoxy-1-[2-(4-methoxy-3-propan-2-yloxyphenyl)ethynyl]benzene
• CAS: 334708-38-2
• 化学式: C₂₆H₂₆O₃S
• 分子量: 418.557
• InChiKey: GMOVVWMNRKEURW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  53
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 2-[2'-(3''-isopropoxy-4''-methoxyphenyl)-ethynyl]-5-methoxyphenyl sulfide 在 碘 、 叔丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 2-(3'-isopropoxy-4'-methoxyphenyl)-6-methoxy-3-(3'',4'',5''-trimethoxybenzoyl)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：

  2-碘-5-甲氧基苯胺 在 氢氧化钾 、 tetrafluoroboric acid 、 正丁基锂 、 四丁基硫酸氢铵 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 7.58h， 生成 benzyl 2-[2'-(3''-isopropoxy-4''-methoxyphenyl)-ethynyl]-5-methoxyphenyl sulfide
  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

• [EN] SYNTHESIS FOR THE PREPARATION OF COMPOUNDS FOR SCREENING AS POTENTIAL TUBULIN BINDING AGENTS<br/>[FR] SYNTHESE DESTINEE A LA PREPARATION DE COMPOSES DE CRIBLAGE UTILISES COMME AGENTS DE FIXATION A LA TUBULINE
  申请人：UNIV AUSTRALIAN

  公开号：WO2002060872A1

  公开（公告）日：2002-08-08

  The present invention relates to methods for the synthesis of chemical compounds for screening as potential tubulin polymerization inhibitors. The invention also provides chemical compounds with tubulin polymerization inhibitor activity.

  本发明涉及用于合成化学化合物以用作潜在的微管聚合抑制剂筛选的方法。本发明还提供了具有微管聚合抑制剂活性的化学化合物。
• Synthesis for the preparation of compounds for screening as potential tubulin binding agents
  申请人：Flynn Luke Bernard

  公开号：US20050130221A1

  公开（公告）日：2005-06-16

  The present invention relates to methods for the synthesis of chemical compounds for screening as potential tubulin polymerization inhibitors. The invention also provides chemical compounds with tubulin polymerization inhibitor activity.

  本发明涉及用于合成化学化合物的方法，用于筛选作为潜在微管聚合抑制剂的化合物。本发明还提供具有微管聚合抑制剂活性的化学化合物。
• SYNTHESIS FOR THE PREPARATION OF COMPOUNDS FOR SCREENING AS POTENTIAL TUBULIN BINDING AGENTS
  申请人：THE AUSTRALIAN NATIONAL UNIVERSITY

  公开号：EP1363880A1

  公开（公告）日：2003-11-26
• EP1363880A4
  申请人：——

  公开号：EP1363880A4

  公开（公告）日：2008-10-08
• 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.