5(S)-5-Allyl-1-(1-cyclopropylcyclopent-1-yl)-5-(3,4-dichlorophenyl)piperidin-2-one | 194427-22-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 5(S)-5-Allyl-1-(1-cyclopropylcyclopent-1-yl)-5-(3,4-dichlorophenyl)piperidin-2-one
• 英文别名: (5S)-1-(1-cyclopropylcyclopentyl)-5-(3,4-dichlorophenyl)-5-prop-2-enylpiperidin-2-one
• CAS: 194427-22-0
• 化学式: C₂₂H₂₇Cl₂NO
• 分子量: 392.368
• InChiKey: JIQUPBFLNLZGCQ-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5(S)-5-Allyl-1-(1-cyclopropylcyclopent-1-yl)-5-(3,4-dichlorophenyl)piperidin-2-one 在 二甲基硫 、 三乙酰氧基硼氢化钠 、 臭氧 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (S)-1-(1-Cyclopropyl-cyclopentyl)-5-(3,4-dichloro-phenyl)-5-[2-(3-morpholin-4-yl-azetidin-1-yl)-ethyl]-piperidin-2-one
  参考文献：
  名称：

  Structure–activity relationships of 1-alkyl-5-(3,4-dichlorophenyl)-5-{2-[3-(substituted)-1-azetidinyl]-ethyl}-2-piperidones. Part 2: Improving oral absorption

  摘要：

  A series of piperidone analogues of 1b-q, seeking replacements for the polar sulfamide moiety in clinical candidate UK-224,671- 1a, possessing reduced H-bonding potential as a strategy to improve oral absorption, were prepared. These studies led to the successful identification of In, which demonstrated equivalent pharmacology and metabolic stability to la, and greatly improved oral absorption as assessed in rat PK studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.134
• 作为产物：
  描述：

  1-cyclopropylcyclopentanol 在 lithium aluminium tetrahydride 、 sodium azide 、 sodium hydride 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 16.0h， 生成 5(S)-5-Allyl-1-(1-cyclopropylcyclopent-1-yl)-5-(3,4-dichlorophenyl)piperidin-2-one
  参考文献：
  名称：

  Structure–activity relationships of 1-alkyl-5-(3,4-dichlorophenyl)-5-{2-[3-(substituted)-1-azetidinyl]-ethyl}-2-piperidones. Part 2: Improving oral absorption

  摘要：

  A series of piperidone analogues of 1b-q, seeking replacements for the polar sulfamide moiety in clinical candidate UK-224,671- 1a, possessing reduced H-bonding potential as a strategy to improve oral absorption, were prepared. These studies led to the successful identification of In, which demonstrated equivalent pharmacology and metabolic stability to la, and greatly improved oral absorption as assessed in rat PK studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.134

文献信息

• PIPERIDONE TACHYKININ ANTAGONISTS
  申请人：Pfizer Research and Development Company, N.V./S.A.

  公开号：EP0888337B1

  公开（公告）日：2002-06-05
• US6262075B1
  申请人：——

  公开号：US6262075B1

  公开（公告）日：2001-07-17
• Structure–activity relationships of 1-alkyl-5-(3,4-dichlorophenyl)-5-{2-[3-(substituted)-1-azetidinyl]-ethyl}-2-piperidones. Part 2: Improving oral absorption
  作者：Donald S. Middleton、A. Roderick MacKenzie、Sandra D. Newman、Martin Corless、Andrew Warren、Allan P. Marchington、Barry Jones

  DOI：10.1016/j.bmcl.2005.05.134

  日期：2005.9

  A series of piperidone analogues of 1b-q, seeking replacements for the polar sulfamide moiety in clinical candidate UK-224,671- 1a, possessing reduced H-bonding potential as a strategy to improve oral absorption, were prepared. These studies led to the successful identification of In, which demonstrated equivalent pharmacology and metabolic stability to la, and greatly improved oral absorption as assessed in rat PK studies. (c) 2005 Elsevier Ltd. All rights reserved.