1-(Cyclopenten-1-yl)-3-(4-methoxyphenyl)propan-1-one | 880476-07-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(Cyclopenten-1-yl)-3-(4-methoxyphenyl)propan-1-one
• CAS: 880476-07-3
• 化学式: C₁₅H₁₈O₂
• 分子量: 230.307
• InChiKey: XKAOCMSBGIUXPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(Cyclopenten-1-yl)-3-(4-methoxyphenyl)propan-1-one 在 盐酸 、 sodium tetrahydroborate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Synthesis and SAR of 1,2-trans-(1-hydroxy-3-phenylprop-1-yl)cyclopentane carboxamide derivatives, a new class of sodium channel blockers

  摘要：

  Novel cyclopentane-based 3-phenyl-1-hydroxypropyl compounds were evaluated for inhibitory activity against the peripheral nerve sodium channel Na(v)1.7 and off-target activity against the cardiac potassium channel hERG. The stereochemistry of the hydroxyl group and substitution on the phenyl rings with either fluorinated O-alkyl or alkyl groups were found to be critical, for conferring potency against Na(v)1.7. A benchmark compound from this series displayed efficacy in rat models of inflammatory and neuropathic pain. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.051
• 作为产物：
  描述：

  环戊烯-1-羧酸甲酯 在 异丙基氯化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 1-(Cyclopenten-1-yl)-3-(4-methoxyphenyl)propan-1-one
  参考文献：
  名称：

  Synthesis and SAR of 1,2-trans-(1-hydroxy-3-phenylprop-1-yl)cyclopentane carboxamide derivatives, a new class of sodium channel blockers

  摘要：

  Novel cyclopentane-based 3-phenyl-1-hydroxypropyl compounds were evaluated for inhibitory activity against the peripheral nerve sodium channel Na(v)1.7 and off-target activity against the cardiac potassium channel hERG. The stereochemistry of the hydroxyl group and substitution on the phenyl rings with either fluorinated O-alkyl or alkyl groups were found to be critical, for conferring potency against Na(v)1.7. A benchmark compound from this series displayed efficacy in rat models of inflammatory and neuropathic pain. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.051

文献信息

• Synthesis and SAR of 1,2-trans-(1-hydroxy-3-phenylprop-1-yl)cyclopentane carboxamide derivatives, a new class of sodium channel blockers
  作者：Dong Ok、Chunshi Li、Catherine Abbadie、John P. Felix、Michael H. Fisher、Maria L. Garcia、Gregory J. Kaczorowski、Kathryn A. Lyons、William J. Martin、Birgit T. Priest、McHardy M. Smith、Brande S. Williams、Matthew J. Wyvratt、William H. Parsons

  DOI：10.1016/j.bmcl.2005.11.051

  日期：2006.3

  Novel cyclopentane-based 3-phenyl-1-hydroxypropyl compounds were evaluated for inhibitory activity against the peripheral nerve sodium channel Na(v)1.7 and off-target activity against the cardiac potassium channel hERG. The stereochemistry of the hydroxyl group and substitution on the phenyl rings with either fluorinated O-alkyl or alkyl groups were found to be critical, for conferring potency against Na(v)1.7. A benchmark compound from this series displayed efficacy in rat models of inflammatory and neuropathic pain. (C) 2005 Elsevier Ltd. All rights reserved.