5-Amino-7-(4-chlorophenyl)-2-phenyl-2,3-dihydro-1-benzothiophene-4,6-dicarbonitrile | 1428258-98-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 5-Amino-7-(4-chlorophenyl)-2-phenyl-2,3-dihydro-1-benzothiophene-4,6-dicarbonitrile
• 英文别名: 5-amino-7-(4-chlorophenyl)-2-phenyl-2,3-dihydro-1-benzothiophene-4,6-dicarbonitrile
• CAS: 1428258-98-3
• 化学式: C₂₂H₁₄ClN₃S
• 分子量: 387.892
• InChiKey: HWJFLLBWVUOZPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  98.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,5-dihydro-5-phenyl-3(2H)-thiophenone 、 4-氯苯甲醛 、 丙二腈 在 N-甲基吗啉 作用下， 以 乙醇 为溶剂， 以72%的产率得到5-Amino-7-(4-chlorophenyl)-2-phenyl-2,3-dihydro-1-benzothiophene-4,6-dicarbonitrile
  参考文献：
  名称：

  A one-pot domino synthesis and discovery of highly functionalized dihydrobenzo[b]thiophenes as AChE inhibitors

  摘要：

  A library of novel 5-amino-2,7-diaryl-2,3-dihydrobenzo[b]thiophene-4,6-dicarbonitriles have been synthesized regioselectively in good yields through the one-pot domino reactions of 5-aryldihydro-3(2H)-thiophenones, malononitrile and aromatic aldehydes in the presence of morpholine. This transformation presumably involves Knoevenagel condensation-Michael addition-intramolecular Thorpe-Ziegler cyclization-Tautomerization-Elimination sequence of reactions. These compounds were evaluated for their acetylcholinesterase (AChE) inhibitory activity and 5-amino-2,7-bis(4-methoxyphenyl)-2,3-dihydrobenzo[b]thiophene-4,6-dicarbonitrile was found to be the most potent against AChE with IC50 4.16 mu mol/L. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.122

文献信息

• A one-pot domino synthesis and discovery of highly functionalized dihydrobenzo[b]thiophenes as AChE inhibitors
  作者：Veerappan Jeyachandran、Raju Ranjith Kumar、Mohamed Ashraf Ali、Tan Soo Choon

  DOI：10.1016/j.bmcl.2013.01.122

  日期：2013.4

  A library of novel 5-amino-2,7-diaryl-2,3-dihydrobenzo[b]thiophene-4,6-dicarbonitriles have been synthesized regioselectively in good yields through the one-pot domino reactions of 5-aryldihydro-3(2H)-thiophenones, malononitrile and aromatic aldehydes in the presence of morpholine. This transformation presumably involves Knoevenagel condensation-Michael addition-intramolecular Thorpe-Ziegler cyclization-Tautomerization-Elimination sequence of reactions. These compounds were evaluated for their acetylcholinesterase (AChE) inhibitory activity and 5-amino-2,7-bis(4-methoxyphenyl)-2,3-dihydrobenzo[b]thiophene-4,6-dicarbonitrile was found to be the most potent against AChE with IC50 4.16 mu mol/L. (C) 2013 Elsevier Ltd. All rights reserved.