6-(3,4-dimethoxyphenyl)amino-2,3,4,7-tetramethylbenzo[b]thiophene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-(3,4-dimethoxyphenyl)amino-2,3,4,7-tetramethylbenzo[b]thiophene
• 英文别名: N-(3,4-dimethoxyphenyl)-2,3,4,7-tetramethyl-1-benzothiophen-6-amine
• 化学式: C₂₀H₂₃NO₂S
• 分子量: 341.474
• InChiKey: LSNQILMZTDOIEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-bromo-2,3,4,7-tetramethylbenzo[b]thiophene 、 3,4-二甲氧基苯胺 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 17.0h， 以52%的产率得到6-(3,4-dimethoxyphenyl)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.