methyl 3-(4-cyanophenylamino)-6-methoxybenzo[b]thiophene-2-carboxylate

• 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-(4-cyanophenylamino)-6-methoxybenzo[b]thiophene-2-carboxylate
• 英文别名: Methyl 3-(4-cyanoanilino)-6-methoxy-1-benzothiophene-2-carboxylate；methyl 3-(4-cyanoanilino)-6-methoxy-1-benzothiophene-2-carboxylate
• 化学式: C₁₈H₁₄N₂O₃S
• 分子量: 338.387
• InChiKey: AGGLEPQWOKJEDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  99.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-溴苯腈 、 3-氨基-6-甲氧基-1-苯并[b]噻吩-2-羧酸甲酯 在 palladium diacetate caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以30%的产率得到methyl 3-(4-cyanophenylamino)-6-methoxybenzo[b]thiophene-2-carboxylate
  参考文献：
  名称：

  Reactivity of several deactivated 3-aminobenzo[b]thiophenes in the Buchwald–Hartwig C–N coupling. Scope and limitations

  摘要：

  Di(hetero)arylamines were prepared in moderate to high yields by Buchwald-Hartwig C-N coupling of bromobenzenes bearing electron-withdrawing groups and of a bromobiphenyl with several methyl 3-aminobenzo[b]thiophene-2-carboxylates, using the coupling conditions for heteroaromatic amines [Pd(OAc)(2), Xantphos, CS2CO3 in dioxane, 120 degrees C]. The use of these aminobenzo[b]thiophenes as coupling components avoids the step of changing the amino group into a bromine atom, like we have done before to perform C-N couplings using the corresponding 3-bromobenzo[b]thiophenes. Nevertheless, the Couplings using the methyl 3-aminobenzo[b]thiophene-2-carboxylates were only successful with bromobenzenes bearing electron-withdrawing groups and a bromobiphenyl or with electron deficient rings such us as bromopyridines. Using the latter compounds, different substituted 6H-benzothieno[3,2-d]pyrido[1,2-a]pyrimid-6-ones were obtained by C-N coupling followed by an intramolecular cyclization. These tetracyclic compounds may have interesting biological activity like it was already demonstrated by us for the non substituted derivative. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.10.029

文献信息

• Reactivity of several deactivated 3-aminobenzo[b]thiophenes in the Buchwald–Hartwig C–N coupling. Scope and limitations
  作者：Maria-João R.P. Queiroz、Ricardo C. Calhelha、Gilbert Kirsch

  DOI：10.1016/j.tet.2007.10.029

  日期：2007.12

  Di(hetero)arylamines were prepared in moderate to high yields by Buchwald-Hartwig C-N coupling of bromobenzenes bearing electron-withdrawing groups and of a bromobiphenyl with several methyl 3-aminobenzo[b]thiophene-2-carboxylates, using the coupling conditions for heteroaromatic amines [Pd(OAc)(2), Xantphos, CS2CO3 in dioxane, 120 degrees C]. The use of these aminobenzo[b]thiophenes as coupling components avoids the step of changing the amino group into a bromine atom, like we have done before to perform C-N couplings using the corresponding 3-bromobenzo[b]thiophenes. Nevertheless, the Couplings using the methyl 3-aminobenzo[b]thiophene-2-carboxylates were only successful with bromobenzenes bearing electron-withdrawing groups and a bromobiphenyl or with electron deficient rings such us as bromopyridines. Using the latter compounds, different substituted 6H-benzothieno[3,2-d]pyrido[1,2-a]pyrimid-6-ones were obtained by C-N coupling followed by an intramolecular cyclization. These tetracyclic compounds may have interesting biological activity like it was already demonstrated by us for the non substituted derivative. (c) 2007 Elsevier Ltd. All rights reserved.