benzyl 2-iodo-5-methoxyphenyl sulfide | 334708-19-9

• 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-iodo-5-methoxyphenyl sulfide
• 英文别名: 2-benzylsulfanyl-1-iodo-4-methoxybenzene
• CAS: 334708-19-9
• 化学式: C₁₄H₁₃IOS
• 分子量: 356.227
• InChiKey: NFNDOVHRNLIJKS-UHFFFAOYSA-N

物化性质

• 沸点：
  400.0±42.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  benzyl 2-iodo-5-methoxyphenyl sulfide 在 正丁基锂 、 碘 、 叔丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.33h， 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 、 四丁基硫酸氢铵 、 sodium nitrite 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 6.25h， 生成 benzyl 2-iodo-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。
• SUBSTITUTED BENZOFURANS, BENZOTHIOPHENES, BENZOSELENOPHENES AND INDOLES AND THEIR USE AS TUBULIN POLYMERISATION INHIBITORS
  申请人：Chaplin Jason Hugh

  公开号：US20100004208A1

  公开（公告）日：2010-01-07

  The present invention relates generally to substituted benzofurans, benzothiophenes, and indoles and their use as tubulin polymerisation inhibitors.

  本发明涉及取代苯并呋喃、苯并噻吩和吲哚，以及它们作为微管聚合抑制剂的用途。
• Substituted benzofurans, benzothiophenes, benzoselenophenes and indoles and their use as tubulin polymerisation inhibitors
  申请人：Bionomics Limited

  公开号：US08198466B2

  公开（公告）日：2012-06-12

  The present invention relates generally to substituted benzofurans, benzothiophenes, and indoles and their use as tubulin polymerization inhibitors.

  本发明涉及取代苯并呋喃、苯并噻吩和吲哚类化合物，并将其用作微管聚合抑制剂。
• Substituted Benzofurans, Benzothiophenes, Benzoselenophenes and Indoles And Their Use as Tubulin Polymerisation Inhibitors
  申请人：Bionomics Limited

  公开号：EP2460793A1

  公开（公告）日：2012-06-06

  The present invention relates generally to substituted benzofurans, benzothiophenes, and indoles and their use as tubulin polymerisation inhibitors. wherein; X represents O, S, SO, SO2, Se, SeO, SeO2 or NR where R is selected from H, O, optionally substituted acyl, optionally substituted alkenyl, optionally substituted alkyl, optionally substituted aryl, optionally substituted cycloalkenyl, optionally substituted cycloalkyl, optionally substituted heteroaryl, optionally substituted heterocyclyl, and optionally substituted sulfonyl; R1C represents C1-3 alkoxy, C1-3 alkylthio, C1-3 alkylamino, or C1-3 dialkylamino; R1D represents hydroxy or amino; L represents C=O, O, S, SO, SO2, Se, SeO, SeO2, C=NZ', or NR' where Z' is H, optionally substituted alkyl, optionally substituted aryl or optionally substituted amino; and where R' is selected from H, O, optionally substituted acyl, optionally substituted alkenyl, optionally substituted alkyl, optionally substituted aryl, optionally substituted cycloalkenyl, optionally substituted cycloalkyl, optionally substituted heteroaryl, optionally substituted heterocyclyl, or optionally substituted sulfonyl; The other variables are as defined in the claims.

  本发明一般涉及取代的苯并呋喃、苯并噻吩和吲哚，以及它们作为微管蛋白聚合抑制剂的用途。 其中 X代表O、S、SO、SO2、Se、SeO、SeO2或NR，其中R选自H、O、任选取代的酰基、任选取代的烯基、任选取代的烷基、任选取代的芳基、任选取代的环烯基、任选取代的环烷基、任选取代的杂芳基、任选取代的杂环基和任选取代的磺酰基； R1C 代表 C1-3 烷氧基、C1-3 烷硫基、C1-3 烷氨基或 C1-3 二烷基氨基； R1D 代表羟基或氨基； L 代表 C=O、O、S、SO、SO2、Se、SeO、SeO2、C=NZ'或 NR'，其中 Z'是 H、任选取代的烷基、任选取代的芳基或任选取代的氨基；R'选自 H、O、任选取代的酰基、任选取代的烯基、任选取代的烷基、任选取代的芳基、任选取代的环烯基、任选取代的环烷基、任选取代的杂芳基、任选取代的杂环基或任选取代的磺酰基； 其他变量如权利要求中所定义。