1-[(3S,4R)-3-hydroxy-2,2-dimethyl-3,4-dihydropyrano[3,2-c]pyridin-4-yl]piperidin-2-one | 219724-55-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: 1-[(3S,4R)-3-hydroxy-2,2-dimethyl-3,4-dihydropyrano[3,2-c]pyridin-4-yl]piperidin-2-one
• CAS: 219724-55-7
• 化学式: C₁₅H₂₀N₂O₃
• 分子量: 276.335
• InChiKey: WDPWNDGJWLWQJP-KGLIPLIRSA-N

物化性质

• 沸点：
  465.702±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.236±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  62.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-(-)-1-苯乙基异氰酸酯 、 1-[(3S,4R)-3-hydroxy-2,2-dimethyl-3,4-dihydropyrano[3,2-c]pyridin-4-yl]piperidin-2-one 以 甲苯 为溶剂， 反应 24.0h， 以0.94 g的产率得到[(3S,4R)-2,2-dimethyl-4-(2-oxopiperidin-1-yl)-3,4-dihydropyrano[3,2-c]pyridin-3-yl] N-[(1S)-1-phenylethyl]carbamate
  参考文献：
  名称：

  Chromatographic resolution of antihypertensive benzopyrans by closed-loop recycling enantioselective high pressure preparative chromatography and their X-ray analysis

  摘要：

  The resolution of (+)-trans-3,4-dihydro-2,2-dimethyl-4-(2-oxopiperidin-1-yl)-2H-pyrano[3,2-c]pyridin-3-ol 1,(1) a potassium channel opener, has been achieved using closed-loop recycling enantioselective preparative chromatography. The resolved enantiomers showed an ee of >97% based on analytical HPLC and H-1 NMR. The absolute configuration has been determined by X-ray analysis of the (R)-(+)-alpha-methylphenylcarbamoyl derivative of one of the enantiomers. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00461-3
• 作为产物：
  描述：

  ((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (3S,4R)-2,2-dimethyl-4-(2-oxo-piperidin-1-yl)-3,4-dihydro-2H-pyrano[3,2-c]pyridin-3-yl ester 在 甲醇 、 sodium methylate 作用下， 反应 3.0h， 以88.6%的产率得到1-[(3S,4R)-3-hydroxy-2,2-dimethyl-3,4-dihydropyrano[3,2-c]pyridin-4-yl]piperidin-2-one
  参考文献：
  名称：

  Chromatographic resolution of antihypertensive benzopyrans by closed-loop recycling enantioselective high pressure preparative chromatography and their X-ray analysis

  摘要：

  The resolution of (+)-trans-3,4-dihydro-2,2-dimethyl-4-(2-oxopiperidin-1-yl)-2H-pyrano[3,2-c]pyridin-3-ol 1,(1) a potassium channel opener, has been achieved using closed-loop recycling enantioselective preparative chromatography. The resolved enantiomers showed an ee of >97% based on analytical HPLC and H-1 NMR. The absolute configuration has been determined by X-ray analysis of the (R)-(+)-alpha-methylphenylcarbamoyl derivative of one of the enantiomers. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00461-3

文献信息

• BURRELL, GORDON;CASSIDY, FREDERICK;EVANS, JOHN M.;LIGHTOWLER, DIANE;STEMP+, J. MED. CHEM., 33,(1990) N1, C. 3023-3027
  作者：BURRELL, GORDON、CASSIDY, FREDERICK、EVANS, JOHN M.、LIGHTOWLER, DIANE、STEMP+

  DOI：——

  日期：——
• Pyrano[3,2-c]pyridine derivatives, process and intermediates for their preparation and pharmaceutical compositions containing them
  申请人：BEECHAM GROUP PLC

  公开号：EP0205292B1

  公开（公告）日：1991-11-06
• US4812459A
  申请人：——

  公开号：US4812459A

  公开（公告）日：1989-03-14
• US4904784A
  申请人：——

  公开号：US4904784A

  公开（公告）日：1990-02-27
• [EN] USE OF POTASSIUM CHANNEL ACTIVATORS FOR THE MANUFACTURE OF A MEDICAMENT FOR THE TREATMENT OF PAIN<br/>[FR] UTILISATION D'ACTIVATEURS DES VANNES A POTASSIUM POUR LA FABRICATION D'UN MEDICAMENT CONTRE LA DOULEUR
  申请人：SMITHKLINE BEECHAM PLC.

  公开号：WO1994013272A1

  公开（公告）日：1994-06-23

  (EN) A method for the treatment of pain in mammals, which comprises administering to the mammal in need of such treatment an effective amount of a potassium channel activator.(FR) Méthode de traitement de la douleur chez les mammifères, qui consiste à leur administrer une dose efficace d'un activateur des vannes à potassium.