6-amino-2,3,5-trimethylbenzo[b]thiophene | 22988-70-1

• 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: 6-amino-2,3,5-trimethylbenzo[b]thiophene
• 英文别名: 2,3,5-Trimethylbenzothiophen-6-amine；2,3,5-trimethyl-1-benzothiophen-6-amine
• CAS: 22988-70-1
• 化学式: C₁₁H₁₃NS
• 分子量: 191.297
• InChiKey: DGSJTBVANZVQMW-UHFFFAOYSA-N

物化性质

• 沸点：
  356.2±37.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  54.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,4-三溴苯 、 6-amino-2,3,5-trimethylbenzo[b]thiophene 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 7.0h， 以35%的产率得到6-(2,4-dibromophenyl)amino-2,3,5-trimethylbenzo[b]thiophene
  参考文献：
  名称：

  钯催化的胺化和环化成杂化的吲哚和咔唑

  摘要：

  通过钯催化的胺化反应，可以在苯或噻吩环中制备苯并[ b ]噻吩系列的新邻溴二芳基胺。将它们在不同的条件下进行钯催化的环化反应，得到几种不同取代的噻吩并[3,2- c ]或[2,3- b ]咔唑和吲哚并[3,2- b ]苯并[ b ]噻吩。这构成了通往两个四环系统的新颖合成途径。

  DOI：

  10.1016/s0040-4020(03)00552-0
• 作为产物：
  描述：

  6-溴-2,3,5-三甲基-1-苯并噻吩 在 盐酸 、 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 22.25h， 生成 6-amino-2,3,5-trimethylbenzo[b]thiophene
  参考文献：
  名称：

  Synthesis of diarylamines in the benzo[b]thiophene series bearing electron donating or withdrawing groups by Buchwald–Hartwig C–N coupling

  摘要：

  Diarylamines in the benzo[b]thiophene series bearing electron donating or withdrawing groups, were prepared by Buchwald-Hartwig C-N coupling in moderate to high yields. The conditions used were Pd(OAc)(2) (3 mol%), BINAP as ligand (4 mol%) and Cs2Co3 as base (1.4 equiv.), in toluene at 100degreesC, being 6-bromo or amino benzo[b]thiophenes coupled, respectively, with substituted anilines or phenylbromides. The 6-aminobenzo[b]thiophene derivatives were also prepared by palladium catalyzed C-N coupling of the corresponding 6-bromo compounds with benzophenone imine, followed by acidic hydrolysis of the imino derivatives. When 4-nitrobromobenzene and 4-bromobenzonitrile were used as coupling components, triarylamines were also isolated in small amounts. The presence of a fluorine atom on the phenylbromide highly increases the diarylamine yields. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01656-3

文献信息

• Novel synthetic routes to thienocarbazoles via palladium or copper catalyzed amination or amidation of arylhalides and intramolecular cyclization
  作者：Isabel C.F.R Ferreira、Maria-João R.P Queiroz、Gilbert Kirsch

  DOI：10.1016/s0040-4020(02)00904-3

  日期：2002.9

  thienocarbazoles. Other method of intramolecular cyclization of diarylamines based on the reoxidation of the Pd(0) formed by Cu(OAc)2, avoiding the use of stoichiometric amounts of Pd(OAc)2, gave thienocarbazoles in a moderate yield, including a ring A methoxylated compound. An attempt to combine palladium and copper catalyses in a ‘one pot’ reaction of amination and intramolecular cyclization gave as major product

  进行钯或铜催化的胺化或酰胺化反应以获得噻吩并咔唑的二芳基胺和二芳基乙酰胺前体。在已知邻位卤代二苯胺的咔唑条件下，邻溴二芳基胺未环化为相应的噻吩并咔唑的事实使我们获得了一种钯催化的分子内环化反应的高效方法，其中邻卤代二芳基乙酰胺N脱保护为噻吩并咔唑。基于由Cu（OAc）2形成的Pd（0）的再氧化避免二芳基胺分子内环化的其他方法，避免使用化学计量的Pd（OAc）2得到适量产率的噻吩并咔唑，包括环A甲氧基化化合物。尝试在胺化和分子内环化的“一锅法”反应中结合钯和铜催化剂，以低收率得到N-苯并[ b ]噻吩取代的咔唑和所需的噻吩并咔唑作为主要产物。
• Synthesis of diarylamines in the benzo[b]thiophene series bearing electron donating or withdrawing groups by Buchwald–Hartwig C–N coupling
  作者：Isabel C.F.R Ferreira、Maria-João R.P Queiroz、Gilbert Kirsch

  DOI：10.1016/s0040-4020(02)01656-3

  日期：2003.2

  Diarylamines in the benzo[b]thiophene series bearing electron donating or withdrawing groups, were prepared by Buchwald-Hartwig C-N coupling in moderate to high yields. The conditions used were Pd(OAc)(2) (3 mol%), BINAP as ligand (4 mol%) and Cs2Co3 as base (1.4 equiv.), in toluene at 100degreesC, being 6-bromo or amino benzo[b]thiophenes coupled, respectively, with substituted anilines or phenylbromides. The 6-aminobenzo[b]thiophene derivatives were also prepared by palladium catalyzed C-N coupling of the corresponding 6-bromo compounds with benzophenone imine, followed by acidic hydrolysis of the imino derivatives. When 4-nitrobromobenzene and 4-bromobenzonitrile were used as coupling components, triarylamines were also isolated in small amounts. The presence of a fluorine atom on the phenylbromide highly increases the diarylamine yields. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Screening of antimicrobial activity of diarylamines in the 2,3,5-trimethylbenzo[b]thiophene series: a structure–activity evaluation study
  作者：Isabel C.F.R. Ferreira、Ricardo C. Calhelha、Letícia M. Estevinho、Maria-João R.P. Queiroz

  DOI：10.1016/j.bmcl.2004.09.038

  日期：2004.12

  Gram positive (Bacillus cereus, B. subtilis), Gram negative (Pseudomonas aeruginosa, Escherichia coli) bacteria, and Candida albicans as a representative of fungi were used for screening the in vitro antimicrobial activity of diarylamines in the 2,3,5-trimethylbenzo[b]thiophene series bearing different substituents, synthesized by us using the palladium-catalyzed C-N coupling methodology. The minimal inhibitory concentration (MIC) and structure-activity relationships (SARs) were evaluated. (C) 2004 Elsevier Ltd. All rights reserved.
• Palladium-catalyzed amination and cyclization to heteroannellated indoles and carbazoles
  作者：Isabel C.F.R Ferreira、Maria-João R.P Queiroz、Gilbert Kirsch

  DOI：10.1016/s0040-4020(03)00552-0

  日期：2003.5

  New ortho-bromodiarylamines in the benzo[b]thiophene series were prepared by palladium-catalyzed amination, either in the benzene or in the thiophene ring. These were submitted to palladium-catalyzed cyclization, under different required conditions, to give several differently substituted thieno[3,2-c] or [2,3-b]carbazoles and indolo[3,2-b]benzo[b]thiophenes. This constitutes a novel synthetic route

  通过钯催化的胺化反应，可以在苯或噻吩环中制备苯并[ b ]噻吩系列的新邻溴二芳基胺。将它们在不同的条件下进行钯催化的环化反应，得到几种不同取代的噻吩并[3,2- c ]或[2,3- b ]咔唑和吲哚并[3,2- b ]苯并[ b ]噻吩。这构成了通往两个四环系统的新颖合成途径。