3-iodo-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene | 264142-55-4

• 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: 3-iodo-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene
• 英文别名: 2-(4-methoxyphenyl)-3-iodo-6-methoxybenzo[b]thiophene；3-Iodo-6-methoxy-2-(4-methoxyphenyl)-1-benzothiophene
• CAS: 264142-55-4
• 化学式: C₁₆H₁₃IO₂S
• 分子量: 396.249
• InChiKey: SFGIMVXHXNOGSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-iodo-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 在 盐酸 、 四(三苯基膦)钯 、 水 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 1.0h， 生成 4-[6-Methoxy-2-(4-methoxyphenyl)benzo[b]thien-3-yl]phenol
  参考文献：
  名称：

  Parallel Synthesis of a Desketoraloxifene Analogue Library via Iodocyclization/Palladium-Catalyzed Coupling

  摘要：

  For a future structure-activity relationship (SAR) study, a library of desketoraloxifene analogues has been prepared by parallel synthesis using iodocyclization and subsequent palladium-catalyzed coupling reactions. Points of desketoraloxifene diversification involve the two phenolic hydroxyl groups and the aliphatic amine side chain. This approach affords oxygen bearing 3-iodobenzo[b]thiophenes 4 in excellent yields, which are easily further elaborated using a two-step approach involving Suzuki-Miyaura and Mitsunobu coupling reactions to give multimethoxy-substituted desketoraloxifene analogues 6. Various hydroxyl-substituted desketoraloxifene analogues 7 were subsequently generated by demethylation with BBr(3).

  DOI：

  10.1021/co200090p
• 作为产物：
  描述：

  (5-methoxy-2-((4-methoxyphenyl)ethynyl)phenyl)(methyl)-sulfane 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以95%的产率得到3-iodo-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene
  参考文献：
  名称：

  通过碘环化制备的含氧 3-碘苯并[b]噻吩制备去酮洛昔芬类似物的新方法

  摘要：

  苯并噻吩选择性雌激素受体调节剂 (SERM) 去酮洛昔芬和类似物的正式全合成已通过使用 I 2 的亲电环化从带有富电子芳环的炔烃完成。这种方法以极好的收率提供了含氧的 3-碘苯并 [ b ] 噻吩，使用涉及 Suzuki-Miyaura 和 Mitsunobu 偶联反应的两步方法可以很容易地进一步阐述。

  DOI：

  10.1016/j.tetlet.2010.09.137

文献信息

• An Air-Tolerant Approach to the Carbonylative Suzuki–Miyaura Coupling: Applications in Isotope Labeling
  作者：Andreas Ahlburg、Anders T. Lindhardt、Rolf. H. Taaning、Amalie E. Modvig、Troels Skrydstrup

  DOI：10.1021/jo401696c

  日期：2013.10.18

  Carbonylative Suzuki-Miyaura coupling conditions have been developed that proceed without the exclusion of oxygen and in the presence of nondegassed and nondried solvents. By adapting the method to a two-chamber setup, the direct handling of carbon monoxide, produced from stable CO precursors, is avoided. The protocol afforded the desired benzophenones with excellent functional group tolerance and in good yields. Substituting the CO precursor, in the CO-producing chamber, with its carbon-13 labeled version generated the corresponding carbon-13 labeled benzophenones. Finally, the developed system was applied in the synthesis and isotope labeling of two pharmaceuticals, nordazepam and Tricor.
• Oxone®-mediated halocyclization/demethylation of 2-alkynylthioanisoles with sodium halides towards 3-halobenzo[b]thiophenes
  作者：Xinyu Chen、Zhebing Zhang、Tao Sun、Haokun Cai、Yuzhen Gao、Tao Cai、Tianbo Shang、Yanjuan Luo、Guoqi Yu、Hualiang Shen、Guofeng Wu、Yanlin Hei、Enmin Li、Gang Fan

  DOI：10.1016/j.tetlet.2021.153614

  日期：2022.2
• 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.
• US6087378A
  申请人：——

  公开号：US6087378A

  公开（公告）日：2000-07-11
• US6258826B1
  申请人：——

  公开号：US6258826B1

  公开（公告）日：2001-07-10