(R)-6-(羟甲基)-2-哌啶酮 | 213532-95-7

• 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: (R)-6-(羟甲基)-2-哌啶酮
• 英文名称: (R)-6-hydroxymethyl-piperidin-2-one
• 英文别名: (R)-6-(Hydroxymethyl)piperidin-2-one；(6R)-6-(hydroxymethyl)piperidin-2-one
• CAS: 213532-95-7
• 化学式: C₆H₁₁NO₂
• mdl: MFCD13181561
• 分子量: 129.159
• InChiKey: VMOQVTPKGUXWKA-RXMQYKEDSA-N

物化性质

• 沸点：
  346℃
• 密度：
  1.098
• 闪点：
  163℃

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-6-(羟甲基)-2-哌啶酮 在 dimethyl sulfide borane 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 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
• 作为产物：
  描述：

  D-2-氨基己二酸 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 生成 (R)-6-(羟甲基)-2-哌啶酮
  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。
• THERAPEUTIC SUBSTITUTED LACTAMS
  申请人：Old David W.

  公开号：US20090209538A1

  公开（公告）日：2009-08-20

  Herein are described compounds having a structure or a pharmaceutically acceptable salt thereof, wherein Y, A, and B are as described. Methods, compositions, and medicaments related thereto are also disclosed.

  这里描述了具有结构或其药用可接受盐的化合物，其中Y、A和B如所述。还公开了相关的方法、组合物和药物。
• EP4 receptor agonist, compositions and methods thereof
  申请人：——

  公开号：US20040198701A1

  公开（公告）日：2004-10-07

  This invention relates to potent selective agonists of the EP 4 subtype of prostaglandin E2 receptors, their use or a formulation thereof in the treatment of glaucoma and other conditions, which are related to elevated intraocular pressure in the eye of a patient. This invention further relates to the use of the compounds of this invention for mediating the bone modeling and remodeling processes of the osteoblasts and osteoclasts.

  这项发明涉及到前列腺素E2受体EP4亚型的强效选择性激动剂，以及它们在治疗青光眼和其他与患者眼内高眼压相关的疾病中的使用或配方。此发明还涉及将本发明的化合物用于介导成骨细胞和破骨细胞的骨建模和重塑过程。
• Piperidinyl prostaglandin E analogs
  申请人：ALLERGAN, INC.

  公开号：US20040248854A1

  公开（公告）日：2004-12-09

  The present invention provides a method of treating ocular hypertension or glaucoma which comprises administering to an animal having ocular hypertension or glaucoma therapeutically effective amount of a compound represented by the general formula I; 1 wherein X, Y, Z, D and R 3 are as defined in the specification. Also disclosed are compounds comprising 2 or a pharmaceutically acceptable salt or a prodrug thereof; wherein A, X, J, and R 3 are as defined in the specification. Also disclosed are compounds having an &agr; and an &ohgr; chain comprising 3 or derivatives thereof, as defined in the specification or pharmaceutically acceptable salts or prodrugs thereof.

  本发明提供了一种治疗眼压增高或青光眼的方法，包括向患有眼压增高或青光眼的动物施用一定剂量的通式I代表的化合物；其中X、Y、Z、D和R3如规范中定义。还披露了包括2或其药用盐或前药的化合物；其中A、X、J和R3如规范中定义。还披露了具有α和ω链的化合物，包括3或其衍生物，如规范中定义，或其药用盐或前药。
• Treatment of inflammatory bowel disease
  申请人：Old W. David

  公开号：US20050171062A1

  公开（公告）日：2005-08-04

  The present invention provides a method of treating inflammatory bowel disease which comprises administering to an animal having ocular hypertension or glaucoma therapeutically effective amount of a compound represented by the general formula 1; wherein X, Y, Z, D and R 3 are as defined in the specification. Also useful for the treatment of inflammatory bowel disease are compounds comprising or a pharmaceutically acceptable salt or a prodrug thereof; wherein A, X, J, and R 3 are as defined in the specification. Also useful for the treatment of inflammatory bowel disease are compounds having an α and an ω chain comprising or derivatives thereof, as defined in the specification or pharmaceutically acceptable salts or prodrugs thereof.

  本发明提供了一种治疗炎症性肠病的方法，包括向患有眼压增高或青光眼的动物施用一定疗效的一般式1代表的化合物；其中X、Y、Z、D和R3如规范中所定义。还可用于治疗炎症性肠病的化合物包括或其药用盐或前药；其中A、X、J和R3如规范中所定义。还可用于治疗炎症性肠病的化合物包括具有α和ω链或其衍生物，如规范中所定义或其药用盐或前药。