6-amino-2,3,4,7-tetramethylbenzo[b]thiophene | 539821-99-3

• 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-2,3,4,7-tetramethylbenzo[b]thiophene
• 英文别名: 2,3,4,7-Tetramethyl-1-benzothiophen-6-amine
• CAS: 539821-99-3
• 化学式: C₁₂H₁₅NS
• 分子量: 205.324
• InChiKey: PFGBQEKIRTYGHJ-UHFFFAOYSA-N

物化性质

• 沸点：
  373.2±37.0 °C(Predicted)
• 密度：
  1.138±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  间溴苯甲醚 、 6-amino-2,3,4,7-tetramethylbenzo[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50%的产率得到6-(3-methoxyphenyl)amino-2,3,4,7-tetramethylbenzo[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
• 作为产物：
  描述：

  6-bromo-2,3,4,7-tetramethylbenzo[b]thiophene 在 盐酸 、 tris(dibenzylideneacetone)dipalladium (0) 、 sodium methylate 、 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 26.25h， 生成 6-amino-2,3,4,7-tetramethylbenzo[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

• 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.