Z-4-ethoxycarbonylmethylene-4,5,6,7-tetrahydrobenzothiophene | 101926-49-2

• 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: Z-4-ethoxycarbonylmethylene-4,5,6,7-tetrahydrobenzothiophene
• 英文别名: (Z)-ethyl 2-(6,7-dihydrobenzo[b]thiophen-4(5H)-ylidene)acetate；ethyl 2-[(4Z)-4,5,6,7-tetrahydro-1-benzothiophen-4-ylidene]acetate；ethyl (2Z)-2-(6,7-dihydro-5H-1-benzothiophen-4-ylidene)acetate
• CAS: 101926-49-2
• 化学式: C₁₂H₁₄O₂S
• 分子量: 222.308
• InChiKey: AQGNEFZJJNGJCC-HJWRWDBZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-(2-噻吩基)丁酸 在 氯化亚砜 、 sodium ethanolate 、 tin(ll) chloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.25h， 生成 Z-4-ethoxycarbonylmethylene-4,5,6,7-tetrahydrobenzothiophene 、 ethyl (6,7-dihydro-5H-benzo[b]thiophen-4-ylidene)acetate
  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