6R-(5-cyclopropyl-3S-hydroxy-pent-1E-enyl)-1-(2-hydroxyethyl)-piperidin-2-one | 724705-98-0

• 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: 6R-(5-cyclopropyl-3S-hydroxy-pent-1E-enyl)-1-(2-hydroxyethyl)-piperidin-2-one
• 英文别名: (6R)-6-[(E,3S)-5-cyclopropyl-3-hydroxypent-1-enyl]-1-(2-hydroxyethyl)piperidin-2-one
• CAS: 724705-98-0
• 化学式: C₁₅H₂₅NO₃
• 分子量: 267.368
• InChiKey: HIJQJRKUBONRNH-QPJKDDTCSA-N

物化性质

• 沸点：
  464.8±40.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6R-(5-cyclopropyl-3S-hydroxy-pent-1E-enyl)-1-(2-hydroxyethyl)-piperidin-2-one 在 sodium hydroxide 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 4-{2-[(R)-2-((S)-(E)-5-Cyclopropyl-3-hydroxy-pent-1-enyl)-6-oxo-piperidin-1-yl]-ethylsulfanyl}-butyric Acid
  参考文献：
  名称：

  Lactams as prostanoid receptor ligands. Part 4: 2-Piperidones as selective EP4 receptor agonists

  摘要：

  2-Piperidones were prepared bearing heptanoic acid or a thioether heptanoic acid at the I-position as well as appropriately substituted at the 6-position to mimic the structure of prostaglandins. The stereochemical purity at the 6-position was determined to be >= 95% ee for an advanced synthetic intermediate. The 2-piperidones were identified as potent agonists at the EP4 prostanoid receptor. They displayed a high affinity (K-i 5-130 nM) at EP4 and subtype selectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.059
• 作为产物：
  描述：

  D-2-氨基己二酸 在 sodium tetrahydroborate 、 dimethyl sulfide borane 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三氟乙酸 、 potassium iodide 、 lithium chloride 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.08h， 生成 6R-(5-cyclopropyl-3S-hydroxy-pent-1E-enyl)-1-(2-hydroxyethyl)-piperidin-2-one
  参考文献：
  名称：

  Lactams as prostanoid receptor ligands. Part 4: 2-Piperidones as selective EP4 receptor agonists

  摘要：

  2-Piperidones were prepared bearing heptanoic acid or a thioether heptanoic acid at the I-position as well as appropriately substituted at the 6-position to mimic the structure of prostaglandins. The stereochemical purity at the 6-position was determined to be >= 95% ee for an advanced synthetic intermediate. The 2-piperidones were identified as potent agonists at the EP4 prostanoid receptor. They displayed a high affinity (K-i 5-130 nM) at EP4 and subtype selectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.059

文献信息

• 2-Piperidone derivatives as prostaglandin agonists
  申请人：——

  公开号：US20040142969A1

  公开（公告）日：2004-07-22

  The invention provides compounds of the Formula: 1 wherein m, n, A, X, Y, Z, R 1 , R 2 , R 4 , R 6 , R 7 , R 8 , R 9 and R 10 are as defined herein, and pharmaceutically acceptable salts, solvates, prodrugs, single isomers or racemic or non-racemic mixture of isomers thereof. The invention also provides methods for preparing, compositions comprising, and methods for using compounds of formula I.

  这项发明提供了以下式的化合物： 1 其中m、n、A、X、Y、Z、R 1 、R 2 、R 4 、R 6 、R 7 、R 8 、R 9 和R 10 如本文所定义，并且其药学上可接受的盐、溶剂化合物、前药、单一异构体或其拉克米或非拉克米异构体混合物。该发明还提供了制备、包含、以及使用式I化合物的方法。
• 2-Piperidone derivatives as prostaglandin antagonists
  申请人：Elworthy Richard Todd

  公开号：US20080058375A1

  公开（公告）日：2008-03-06

  The invention provides compounds of the Formula: wherein m, n, A, X, Y, Z, R 1 , R 2 , R 4 , R 6 , R 7 , R 8 , R 9 and R 10 are as defined herein, and pharmaceutically acceptable salts, solvates, prodrugs, single isomers or racemic or non-racemic mixture of isomers thereof. The invention also provides methods for preparing, compositions comprising, and methods for using compounds of formula I.

  该发明提供了公式为：其中m，n，A，X，Y，Z，R1，R2，R4，R6，R7，R8，R9和R10的化合物的药学上可接受的盐，溶剂化合物，前药，单一异构体或其外消旋或非消旋异构体的混合物。该发明还提供了制备公式I化合物的方法，包含公式I化合物的组合物的方法，以及使用公式I化合物的方法。
• US7271183B2
  申请人：——

  公开号：US7271183B2

  公开（公告）日：2007-09-18
• Lactams as prostanoid receptor ligands. Part 4: 2-Piperidones as selective EP4 receptor agonists
  作者：Todd R. Elworthy、Emma R. Brill、Christopher C. Caires、Woongki Kim、Leang K. Lach、Jahari Laurant Tracy、San-San Chiou

  DOI：10.1016/j.bmcl.2005.03.059

  日期：2005.5

  2-Piperidones were prepared bearing heptanoic acid or a thioether heptanoic acid at the I-position as well as appropriately substituted at the 6-position to mimic the structure of prostaglandins. The stereochemical purity at the 6-position was determined to be >= 95% ee for an advanced synthetic intermediate. The 2-piperidones were identified as potent agonists at the EP4 prostanoid receptor. They displayed a high affinity (K-i 5-130 nM) at EP4 and subtype selectivity. (c) 2005 Elsevier Ltd. All rights reserved.