N-(cyclohexylmethyl)-2-(4,5,6,7-tetrahydrobenzo[b]thiophen-4-yl)acetamide | 1489217-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: N-(cyclohexylmethyl)-2-(4,5,6,7-tetrahydrobenzo[b]thiophen-4-yl)acetamide
• CAS: 1489217-40-4
• 化学式: C₁₇H₂₅NOS
• 分子量: 291.458
• InChiKey: GOHAZDOMCNLFMN-UHFFFAOYSA-N

物化性质

• 熔点：
  87-91 °C
• 沸点：
  490.7±25.0 °C(predicted)
• 密度：
  1.086±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-(cyclohexylmethyl)-2-(4,5,6,7-tetrahydrobenzo[b]thiophen-4-yl)acetamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以42%的产率得到N-(cyclohexylmethyl)-2-(4,5,6,7-tetrahydrobenzo[b]thiophen-4-yl)ethanamine
  参考文献：
  名称：

  New combination of pharmacophoric elements of potent σ1 ligands: Design, synthesis and σ receptor affinity of aminoethyl substituted tetrahydrobenzothiophenes

  摘要：

  The aminoethyl substituted tetrahydrobenzothiophenes 4 resulted from combination of the pharmacophoric elements of the potent cri ligands 2 and 3. The aminoethyl substituted tetrahydrobenzothiophenes 4 were prepared in an 8-step synthesis starting with thiophene. Whereas the rri affinity of the N-benzyl derivative 4a is in the medium nanomolar range (K-i = 49 nM), the analogous N-cyclohexylmethyl derivative 4d exhibits low nanomolar affinity (Ki = 5.0 nM). The reduced sigma(1) affinity and sigma(2)/sigma(1) selectivity of tetrahydrobenzothiophenes 4 compared to analogous spirocyclic piperidines 3 is attributed to the increased conformational flexibility of the aminoethyl side chain. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.006
• 作为产物：
  描述：

  E-4-ethoxycarbonylmethylene-4,5,6,7-tetrahydrobenzothiophene 在 palladium on activated charcoal 、 水 、 氢气 、 N,N'-羰基二咪唑 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 16.17h， 生成 N-(cyclohexylmethyl)-2-(4,5,6,7-tetrahydrobenzo[b]thiophen-4-yl)acetamide
  参考文献：
  名称：

  New combination of pharmacophoric elements of potent σ1 ligands: Design, synthesis and σ receptor affinity of aminoethyl substituted tetrahydrobenzothiophenes

  摘要：

  The aminoethyl substituted tetrahydrobenzothiophenes 4 resulted from combination of the pharmacophoric elements of the potent cri ligands 2 and 3. The aminoethyl substituted tetrahydrobenzothiophenes 4 were prepared in an 8-step synthesis starting with thiophene. Whereas the rri affinity of the N-benzyl derivative 4a is in the medium nanomolar range (K-i = 49 nM), the analogous N-cyclohexylmethyl derivative 4d exhibits low nanomolar affinity (Ki = 5.0 nM). The reduced sigma(1) affinity and sigma(2)/sigma(1) selectivity of tetrahydrobenzothiophenes 4 compared to analogous spirocyclic piperidines 3 is attributed to the increased conformational flexibility of the aminoethyl side chain. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.006