3-(cyclohexylethynyl)benzo[b]thiophene-2-carbaldehyde | 1318795-15-1

• 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: 3-(cyclohexylethynyl)benzo[b]thiophene-2-carbaldehyde
• CAS: 1318795-15-1
• 化学式: C₁₇H₁₆OS
• 分子量: 268.379
• InChiKey: LEAOUHKMHFFHPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.65
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(cyclohexylethynyl)benzo[b]thiophene-2-carbaldehyde 在 silver nitrate 、 叔丁胺 作用下， 以 乙醇 为溶剂， 反应 36.0h， 以62%的产率得到3-cyclohexylbenzo[4,5]thieno[2,3-c]pyridine
  参考文献：
  名称：

  Tandem Approach to Benzothieno- and Benzofuropyridines from o-Alkynyl Aldehydes via Silver-Catalyzed 6-endo-dig Ring Closure

  摘要：

  An operationally simple silver-catalyzed tandem strategy for the synthesis of benzothienopyridines 7a-t and benzofuropyridines 8a-p by the reaction of o-alkynyl aldehyde 4a-t and 5a-p with tert-butylamine 6 under mild reaction conditions is described. The present methodology provides a facile conversion of easily accessible o-alkynyl aldehydes into medicinally useful heterocycles in good to excellent yields under mild and environmentally friendly reaction conditions with excellent regioselectivity. The developed chemistry has been successfully extended for the selective synthesis of C-4 deuterated benzothienopyridines 7u-v and benzofurop-yridines 8q-r. The role of the ethanolic proton in the reaction was validated by deuterium-labeling experiments.

  DOI：

  10.1021/acs.joc.5b01647
• 作为产物：
  描述：

  3-溴苯并噻吩-2-甲醛 、 环己基乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 生成 3-(cyclohexylethynyl)benzo[b]thiophene-2-carbaldehyde
  参考文献：
  名称：

  Tandem Approach to Benzothieno- and Benzofuropyridines from o-Alkynyl Aldehydes via Silver-Catalyzed 6-endo-dig Ring Closure

  摘要：

  An operationally simple silver-catalyzed tandem strategy for the synthesis of benzothienopyridines 7a-t and benzofuropyridines 8a-p by the reaction of o-alkynyl aldehyde 4a-t and 5a-p with tert-butylamine 6 under mild reaction conditions is described. The present methodology provides a facile conversion of easily accessible o-alkynyl aldehydes into medicinally useful heterocycles in good to excellent yields under mild and environmentally friendly reaction conditions with excellent regioselectivity. The developed chemistry has been successfully extended for the selective synthesis of C-4 deuterated benzothienopyridines 7u-v and benzofurop-yridines 8q-r. The role of the ethanolic proton in the reaction was validated by deuterium-labeling experiments.

  DOI：

  10.1021/acs.joc.5b01647

文献信息

• Highly efficient Ag(i)-catalyzed regioselective tandem synthesis of diversely substituted quinoxalines and benzimidazoles in water
  作者：Vineeta Rustagi、Trapti Aggarwal、Akhilesh K. Verma

  DOI：10.1039/c1gc15346c

  日期：——

  A green and operationally simple approach for the diverse synthesis of fused quinoxalines and benzimidazoles from o-alkynylaldehydes and amines having an N-tethered nucleophile using Ag(I) as the catalyst in water, is described. The X-ray crystallographic studies confirmed the proposed mechanistic pathway and the cyclized product.

  一种绿色且操作简单的方法，用于合成稠合的喹喔啉和 苯并咪唑由邻炔醛和胺类使用Ag（I）作为分子的N系亲核试剂催化剂 在 水进行说明。X射线晶体学研究证实了拟议的机理途径和环化产物。
• Metal-free regioselective tandem synthesis of diversely substituted benzimidazo-fused polyheterocycles in aqueous medium
  作者：Pawan K. Mishra、Akhilesh K. Verma

  DOI：10.1039/c6gc02330d

  日期：——

  An operationally simple greener approach for the synthesis of diversely substituted benzimidazo-fused polyheterocycles under the metal-free condition in water has been described. The aqueous medium accelerates the formation of desired...

  已经描述了一种在水中无金属条件下合成多种取代的苯并咪唑稠合的多杂环化合物的操作简单的绿色方法。水性介质可加速所需...