2-chloro-5,6-dihydro-4H-cyclopenta[b]thiophen-4-one | 69300-48-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-chloro-5,6-dihydro-4H-cyclopenta[b]thiophen-4-one
• 英文别名: 2-chloro-5,6-dihydrocyclopenta[b]thiophen-4-one
• CAS: 69300-48-7
• 化学式: C₇H₅ClOS
• mdl: MFCD00757252
• 分子量: 172.635
• InChiKey: UAGPCGAVANHCNG-UHFFFAOYSA-N

物化性质

• 沸点：
  288.4±40.0 °C(Predicted)
• 密度：
  1.482±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-chloro-5,6-dihydro-4H-cyclopenta[b]thiophen-4-one 在 Raney nickel W₂ 硫酸 、 氢气 、 硝酸 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 6.0h， 生成 3-Amino-5,6-dihydro-2-phenoxy-4h-cyclopenta[b]thiophen-4-one
  参考文献：
  名称：

  A Facile Route to Functionalized Cyclopenta[b]thiophenones Based on the Structure of the Selective COX-2 Inhibitor Flosulide

  摘要：

  DOI：

  10.1007/pl00013496
• 作为产物：
  描述：

  在 sodium carbonate 作用下， 以 1,1-二氯乙烷 为溶剂， 以105 mg的产率得到2-chloro-5,6-dihydro-4H-cyclopenta[b]thiophen-4-one
  参考文献：
  名称：

  3D Pharmacophore Model-Assisted Discovery of Novel CDC7 Inhibitors

  摘要：

  A ligand-based 3D pharmacophore model for serine/threonine kinase CDC7 inhibition was created and successfully applied in the discovery of novel 2-(heteroaryl)-6,7-dihydrothieno[3,2-c]pyridin-4(5H)-ones. The pharmacophore model provided a hypothesis for lead generation missed by docking to a homology model. Medicinal chemistry exploration of the series revealed clear structure-activity relationships consistent with the pharmacophore model and pointed to further optimization opportunities.

  DOI：

  10.1021/ml200029w

文献信息

• Efficient One-Pot Synthesis of Cyclopenta[b]thiophen-1-ones and 1,3-Di(2-thiophenyl)propan-1-ones from Thiophenes
  作者：Ivan L. Baraznenok、Valentine G. Nenajdenko、Elizabeth S. Balenkova

  DOI：10.1055/s-1997-1207

  日期：1997.4

  The reaction of N,N-dimethylacrylamide/triflic anhydride complex with substituted thiophenes led to the corresponding cyclopenta[b]thiophen-1-ones and 1,3-di(2-thiophenyl)propan-1-ones. The application of 2-bromo-N,N-dimethylacrylamide in this reaction allows 2-bromo-substituted five- or seven-membered thiophene-fused cyclic ketones to be obtained.

  N,N-二甲基丙烯酰胺/三氟乙酸酐复合物与取代噻吩的反应产生了相应的环戊[b]噻吩-1-酮和1,3-二(2-噻吩基)丙酮。该反应中使用2-溴-N,N-二甲基丙烯酰胺能够获得2-溴取代的五元或七元噻吩融合环酮。
• 3D Pharmacophore Model-Assisted Discovery of Novel CDC7 Inhibitors
  作者：Mika Lindvall、Christopher McBride、Maureen McKenna、Thomas G. Gesner、Asha Yabannavar、Kent Wong、Song Lin、Annette Walter、Cynthia M. Shafer

  DOI：10.1021/ml200029w

  日期：2011.10.13

  A ligand-based 3D pharmacophore model for serine/threonine kinase CDC7 inhibition was created and successfully applied in the discovery of novel 2-(heteroaryl)-6,7-dihydrothieno[3,2-c]pyridin-4(5H)-ones. The pharmacophore model provided a hypothesis for lead generation missed by docking to a homology model. Medicinal chemistry exploration of the series revealed clear structure-activity relationships consistent with the pharmacophore model and pointed to further optimization opportunities.
• A Facile Route to Functionalized Cyclopenta[b]thiophenones Based on the Structure of the Selective COX-2 Inhibitor Flosulide
  作者：Dieter Binder、Michael Pyerin、Roman Steindl、Martin Weisgram

  DOI：10.1007/pl00013496

  日期：1998.9