3-(4-tolyl)-2-methoxycarbonylbenzo[b]thiophene | 162154-06-5

• 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-(4-tolyl)-2-methoxycarbonylbenzo[b]thiophene
• 英文别名: Methyl 3-(4-methylphenyl)-1-benzothiophene-2-carboxylate；methyl 3-(4-methylphenyl)-1-benzothiophene-2-carboxylate
• CAS: 162154-06-5
• 化学式: C₁₇H₁₄O₂S
• 分子量: 282.363
• InChiKey: LXNMTMGVZZZSCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 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：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-tolyl)-2-methoxycarbonylbenzo[b]thiophene 在 水 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3-(4-Methylphenyl)-1-benzothiophene-2-carboxylic acid
  参考文献：
  名称：

  2,3- Diarylbenzo的合成[ b ]噻吩通过镍-催化的Suzuki-Miyaura交叉偶联和钯催化脱羧芳基化

  摘要：

  我们报告了一种基于镍催化的3-氯-2-甲氧基羰基苯并[ b ]噻吩的镍催化的铃木-宫浦交叉偶联/钯催化的脱羧芳基化序列的2,3-二芳基苯并[ b ]噻吩的新方法可从相应的肉桂酸中获得。另外，该方法可以应用于简并的π-扩展的2,3,6,7-四芳基苯并[1,2- b ; 4,5- b' ]二噻吩的合成。还描述了它们的光学性质。

  DOI：

  10.1002/adsc.200900480
• 作为产物：
  描述：

  2-硝基苯甲腈 在 potassium phosphate 、 四(三苯基膦)钯 、 亚硝酸特丁酯 、 potassium hydroxide 、 copper(ll) bromide 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 7.0h， 生成 3-(4-tolyl)-2-methoxycarbonylbenzo[b]thiophene
  参考文献：
  名称：

  Design and synthesis of condensed thienocoumarins by Suzuki–Miyaura reaction/lactonization tandem protocol

  摘要：

  A concise and efficient approach to a series of chromen-4-ones with fused thiophene ring has been developed using the Suzuki-Miyaura reaction of bromothiophene-2- and 3-carboxylates with 2-methoxyboronic acids and subsequent cyclization of prepared alkyl (2-methoxy)aryl thiophene-2- and 3-carboxylates under the action of BBr3/KOtBu. Starting bromothiophenes are easily obtained from corresponding commercially available aminothiophenes by diazotization/bromination reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.10.096

文献信息

• Facile Access to Benzothiophenes through Metal-Free Iodine-­Catalyzed Intermolecular Cyclization of Thiophenols and Alkynes
  作者：Daoshan Yang、Hua Wang、Kelu Yan、Mengqi Zhang、Wei Wei、Yao Liu、Laijin Tian

  DOI：10.1055/s-0034-1378841

  日期：——

  A novel iodine-catalyzed method for the synthesis of benzothiophene derivatives through cascade reactions of substituted thiophenols with alkynes has been demonstrated under metal- and solvent-free conditions. The present protocol uses inexpensive and environmentally friendly molecular iodine as the catalyst, and the corresponding products are obtained in moderate to excellent yields. Such an efficient

  在无金属和无溶剂条件下，证明了一种通过取代苯硫酚与炔烃的级联反应合成苯并噻吩衍生物的新型碘催化方法。本协议使用廉价且环保的分子碘作为催化剂, 并以中等至优良的收率获得相应的产品。这种高效、经济和绿色的转化应该为有机和药物化学中的各种苯并噻吩提供一种有吸引力的方法。
• Design and synthesis of condensed thienocoumarins by Suzuki–Miyaura reaction/lactonization tandem protocol
  作者：Viktor O. Iaroshenko、Sajid Ali、Satenik Mkrtchyan、Ashot Gevorgyan、Tariq Mahmood Babar、Volodymyr Semeniuchenko、Zahid Hassan、Alexander Villinger、Peter Langer

  DOI：10.1016/j.tetlet.2012.10.096

  日期：2012.12

  A concise and efficient approach to a series of chromen-4-ones with fused thiophene ring has been developed using the Suzuki-Miyaura reaction of bromothiophene-2- and 3-carboxylates with 2-methoxyboronic acids and subsequent cyclization of prepared alkyl (2-methoxy)aryl thiophene-2- and 3-carboxylates under the action of BBr3/KOtBu. Starting bromothiophenes are easily obtained from corresponding commercially available aminothiophenes by diazotization/bromination reaction. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of 2,3-Diarylbenzo[<i>b</i>]thiophenes<i>via</i>Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling and Palladium-Catalyzed Decarboxylative Arylation
  作者：Mitsuru Miyasaka、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1002/adsc.200900480

  日期：2009.11

  We report a new approach to 2,3-diarylbenzo[b]thiophenes based on the nickel-catalyzed Suzuki–Miyaura cross-coupling/palladium-catalyzed decarboxylative arylation sequence of 3-chloro-2-methoxycarbonylbenzo[b]thiophenes, which are readily accessible from the corresponding cinnamic acids. In addition, this methodology can be applied to the concise synthesis of π-extended 2,3,6,7-tetraarylbenzo[1,2-b;4

  我们报告了一种基于镍催化的3-氯-2-甲氧基羰基苯并[ b ]噻吩的镍催化的铃木-宫浦交叉偶联/钯催化的脱羧芳基化序列的2,3-二芳基苯并[ b ]噻吩的新方法可从相应的肉桂酸中获得。另外，该方法可以应用于简并的π-扩展的2,3,6,7-四芳基苯并[1,2- b ; 4,5- b' ]二噻吩的合成。还描述了它们的光学性质。