2-(4,5,6,7-tetrahydrobenzo[b]thiophen-4-yl)acetic acid

• 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: 2-(4,5,6,7-tetrahydrobenzo[b]thiophen-4-yl)acetic acid
• 英文别名: 2-(4,5,6,7-Tetrahydrobenzo[B]thiophen-4-YL)acetic acid；2-(4,5,6,7-tetrahydro-1-benzothiophen-4-yl)acetic acid
• 化学式: C₁₀H₁₂O₂S
• 分子量: 196.27
• InChiKey: HCTYINCKCYCZKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4,5,6,7-tetrahydrobenzo[b]thiophen-4-yl)acetic acid 在 lithium aluminium tetrahydride 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 为溶剂， 反应 16.17h， 生成 3-phenyl-N-[2-(4,5,6,7-tetrahydrobenzo[b]thiophen-4-yl)ethyl]propan-1-amine
  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：

  4'-(4,5,6,7-Tetrahydrobenzothienyl)ethyl ethanoate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以83%的产率得到2-(4,5,6,7-tetrahydrobenzo[b]thiophen-4-yl)acetic acid
  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

文献信息

• Datta, Sumana; Bhattacharya, Subhra; De, Ashsh, Journal of Chemical Research, Miniprint, 1988, # 2, p. 667 - 683
  作者：Datta, Sumana、Bhattacharya, Subhra、De, Ashsh、Chakravarty, Ajit Kumar

  DOI：——

  日期：——