4-(3-溴苯磺酰基)哌啶-1-羧酸叔丁酯 | 887591-23-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 4-(3-溴苯磺酰基)哌啶-1-羧酸叔丁酯
• 英文名称: Tert-butyl 4-(3-bromophenylsulfonyl)piperidine-1-carboxylate
• 英文别名: tert-butyl 4-(3-bromophenyl)sulfonylpiperidine-1-carboxylate
• CAS: 887591-23-3
• 化学式: C₁₆H₂₂BrNO₄S
• 分子量: 404.325
• InChiKey: FDNNFLGHYKULLI-UHFFFAOYSA-N

物化性质

• 沸点：
  519.1±50.0 °C(Predicted)
• 密度：
  1.403±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3-溴苯磺酰基)哌啶-1-羧酸叔丁酯 在 盐酸 、 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 39.0h， 生成 N-(2,4-difluorophenethyl)-4-(3-(carbomethoxy)phenylsulfonyl)piperidine
  参考文献：
  名称：

  4-(Phenylsulfonyl)piperidines:  Novel, Selective, and Bioavailable 5-HT_2A Receptor Antagonists

  摘要：

  On the basis of a spirocyclic ether screening lead, a series of acyclic sulfones have been identifed as high-affinity, selective 5-HT2A receptor antagonists. Bioavailability lacking in the parent, 1-(2-(2,4-difluorophenyl)ethyl)-4-(phenylsulfonyl)piperidine (12), was introduced by using stability toward rat liver microsomes as a predictor of bioavailability. By this means, the 4-cyano- and 4-carboxamidophenylsulfonyl derivatives 26 and 31 were identified as orally bioavailable, brain-penetrant analogues suitable for evaluation in animal models. Bioavailability was also attainable by N substitution leading to the N-phenacyl derivative 35. IKr activity detected through counterscreening was reduced to insignificant levels in vivo with the latter compound.

  DOI：

  10.1021/jm011030v
• 作为产物：
  描述：

  1-Boc-4-甲烷磺酰氧基哌啶 在 aluminum oxide 、 Oxone 、 potassium carbonate 作用下， 以 氯仿 、 水 、 乙腈 为溶剂， 反应 36.0h， 生成 4-(3-溴苯磺酰基)哌啶-1-羧酸叔丁酯
  参考文献：
  名称：

  4-(Phenylsulfonyl)piperidines:  Novel, Selective, and Bioavailable 5-HT_2A Receptor Antagonists

  摘要：

  On the basis of a spirocyclic ether screening lead, a series of acyclic sulfones have been identifed as high-affinity, selective 5-HT2A receptor antagonists. Bioavailability lacking in the parent, 1-(2-(2,4-difluorophenyl)ethyl)-4-(phenylsulfonyl)piperidine (12), was introduced by using stability toward rat liver microsomes as a predictor of bioavailability. By this means, the 4-cyano- and 4-carboxamidophenylsulfonyl derivatives 26 and 31 were identified as orally bioavailable, brain-penetrant analogues suitable for evaluation in animal models. Bioavailability was also attainable by N substitution leading to the N-phenacyl derivative 35. IKr activity detected through counterscreening was reduced to insignificant levels in vivo with the latter compound.

  DOI：

  10.1021/jm011030v

文献信息

• 4-(Phenylsulfonyl)piperidines:  Novel, Selective, and Bioavailable 5-HT_2A Receptor Antagonists
  作者：Stephen R. Fletcher、Frank Burkamp、Peter Blurton、Susan K. F. Cheng、Robert Clarkson、Desmond O'Connor、Daniel Spinks、Matthew Tudge、Monique B. van Niel、Smita Patel、Kerry Chapman、Rose Marwood、Sara Shepheard、Graham Bentley、Gina P Cook、Linda J Bristow、Jose L. Castro、Peter H. Hutson、Angus M. MacLeod

  DOI：10.1021/jm011030v

  日期：2002.1.1

  On the basis of a spirocyclic ether screening lead, a series of acyclic sulfones have been identifed as high-affinity, selective 5-HT2A receptor antagonists. Bioavailability lacking in the parent, 1-(2-(2,4-difluorophenyl)ethyl)-4-(phenylsulfonyl)piperidine (12), was introduced by using stability toward rat liver microsomes as a predictor of bioavailability. By this means, the 4-cyano- and 4-carboxamidophenylsulfonyl derivatives 26 and 31 were identified as orally bioavailable, brain-penetrant analogues suitable for evaluation in animal models. Bioavailability was also attainable by N substitution leading to the N-phenacyl derivative 35. IKr activity detected through counterscreening was reduced to insignificant levels in vivo with the latter compound.