2-chloro-N-(4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-5-yl)-acetamide | 444559-56-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-chloro-N-(4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-5-yl)-acetamide
• 英文别名: 2-Chloro-N-(4,5,6,7-tetrahydro-4-oxobenzo[b]thien-5-yl)acetamide；2-chloro-N-(4-oxo-6,7-dihydro-5H-1-benzothiophen-5-yl)acetamide
• CAS: 444559-56-2
• 化学式: C₁₀H₁₀ClNO₂S
• 分子量: 243.714
• InChiKey: HHYJAXVNUAFIKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  74.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-5-yl)-acetamide 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 1.0h， 以88%的产率得到trans-2-chloro-N-(4-hydroxy-4,5,6,7-tetrahydrobenzo[b]thiophene-5-yl)-acetamide
  参考文献：
  名称：

  Further Characterization of Structural Requirements for Ligands at the Dopamine D₂ and D₃ Receptor:  Exploring the Thiophene Moiety

  摘要：

  The present study describes the synthesis and in vitro pharmacology of a novel series of dopaminergic agents in which the classical phenylethylamine pharmacophore is replaced by a thienylethylamine moiety. In general, the novel compounds showed a moderate affinity for the dopamine (DA) D-2 and D-3 receptors. When the thienylethylamine moiety is fixed in a rigid system, the affinity for the DA receptor is significantly increased. However, in the tricyclic hexahydrothianaphthoxazine structure, the affinity for the DA receptors is diminished.

  DOI：

  10.1021/jm001015a
• 作为产物：
  描述：

  氯乙酰氯 、 5-amino-6,7-dihydro-5H-benzo[b]thiophene-4-one hydrochloride 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以95%的产率得到2-chloro-N-(4-oxo-4,5,6,7-tetrahydrobenzo[b]thiophene-5-yl)-acetamide
  参考文献：
  名称：

  Further Characterization of Structural Requirements for Ligands at the Dopamine D₂ and D₃ Receptor:  Exploring the Thiophene Moiety

  摘要：

  The present study describes the synthesis and in vitro pharmacology of a novel series of dopaminergic agents in which the classical phenylethylamine pharmacophore is replaced by a thienylethylamine moiety. In general, the novel compounds showed a moderate affinity for the dopamine (DA) D-2 and D-3 receptors. When the thienylethylamine moiety is fixed in a rigid system, the affinity for the DA receptor is significantly increased. However, in the tricyclic hexahydrothianaphthoxazine structure, the affinity for the DA receptors is diminished.

  DOI：

  10.1021/jm001015a