methyl 3-(2-methoxyphenyl)benzo[b]thiophene-2-carboxylate | 1332980-97-8

• 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: methyl 3-(2-methoxyphenyl)benzo[b]thiophene-2-carboxylate
• 英文别名: 3-(2-methoxyphenyl)-2-methoxycarbonylbenzo[b]thiophene；Methyl 3-(2-methoxyphenyl)-1-benzothiophene-2-carboxylate；methyl 3-(2-methoxyphenyl)-1-benzothiophene-2-carboxylate
• CAS: 1332980-97-8
• 化学式: C₁₇H₁₄O₃S
• 分子量: 298.362
• InChiKey: LRTBYWQRVNCYMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-(2-methoxyphenyl)benzo[b]thiophene-2-carboxylate 在 三溴化硼 、 potassium tert-butylate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.25h， 以74%的产率得到6H-[1]benzothieno[2,3-с]chromen-6-one
  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
• 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 methyl 3-(2-methoxyphenyl)benzo[b]thiophene-2-carboxylate
  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

• Functionalization of the 3-Position of Thiophene and Benzo[b]thiophene Moieties by Palladium-Catalyzed CC Bond Forming Reactions using Diazonium Salts
  作者：Mónica Raduán、Joaquim Padrosa、Anna Pla-Quintana、Teodor Parella、Anna Roglans

  DOI：10.1002/adsc.201100226

  日期：2011.8

  Matsuda–Heck and Suzuki–Miyaura cross-couplings of 2-methoxycarbonylthiophene-3-diazonium tetrafluoroborate 1 were performed to synthesize a series of thiophene derivatives functionalized in the β-position. Good to excellent yields of the cross-coupling products were obtained using palladium acetate [Pd(OAc)2], a ligandless palladium catalyst, without a base, at room temperature, under aerobic conditions and with

  2-甲酯基噻吩-3-重氮四氟硼酸盐的钯催化的松田-的Heck和Suzuki-Miyaura交叉偶联1进行到合成一系列在β位官能噻吩衍生物。使用乙酸钯[Pd（OAc）2 ]，一种无配体的钯催化剂，无碱，在室温下，好氧条件下，反应时间短的情况下，可获得良好或优异的交叉偶联产物收率。重氮化和交叉偶联的序列也可以在一锅法中进行，从而避免了噻吩并重氮盐衍生物的分离。此外，2-甲氧基羰基苯并[ b ]噻吩-3-重氮四氟硼酸盐8 通过应用相同的Suzuki-Miyaura优化反应条件也可以有效地芳基化。