4-(3-amino-2-fluoro-4-hydroxy-benzyl)-piperidine-1-carboxylic acid tert-butyl ester | 793670-71-0

• 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: 4-(3-amino-2-fluoro-4-hydroxy-benzyl)-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 4-[(3-amino-2-fluoro-4-hydroxyphenyl)methyl]piperidine-1-carboxylate
• CAS: 793670-71-0
• 化学式: C₁₇H₂₅FN₂O₃
• 分子量: 324.396
• InChiKey: KLWKYEJBSWLFIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  75.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(3-amino-2-fluoro-4-hydroxy-benzyl)-piperidine-1-carboxylic acid tert-butyl ester 在 N-ethyl-diisopropylethylamine 、 三氟乙酸 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 生成 6-(1-(2-(7-fluoro-2-methyl-quinolin-5-yloxy)-ethyl)-piperidin-4-ylmethyl)-5-fluoro-4H-benzo[1,4]oxazin-3-one
  参考文献：
  名称：

  3,4-Dihydro-2H-benzoxazinones as dual-acting 5-HT1A receptor antagonists and serotonin reuptake inhibitors

  摘要：

  Investigation of halogen substitution in lead compound 1 has led to the identification of analogues which combine high affinity for 5-HT1A receptors and potent serotonin reuptake inhibitory activity. Several compounds show an improved selectivity over 5-HT1B and 5-HT1D receptors and a superior pharmacokinetic profile in the rat. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.031
• 作为产物：
  描述：

  在 palladium on activated charcoal potassium tert-butylate 、 氢气 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(3-amino-2-fluoro-4-hydroxy-benzyl)-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  3,4-Dihydro-2H-benzoxazinones as dual-acting 5-HT1A receptor antagonists and serotonin reuptake inhibitors

  摘要：

  Investigation of halogen substitution in lead compound 1 has led to the identification of analogues which combine high affinity for 5-HT1A receptors and potent serotonin reuptake inhibitory activity. Several compounds show an improved selectivity over 5-HT1B and 5-HT1D receptors and a superior pharmacokinetic profile in the rat. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.031

文献信息

• [EN] BENZOXAZINONE DERIVATIVES HAVING AFFINITY FOR 5- HT RECEPTORS, THEIR PREPARATION AND USE<br/>[FR] DERIVES DE BENZOXAZINONE POSSEDANT UNE AFFINITE AVEC DES RECEPTEURS 5-HT, PREPARATION ET UTILISATION DE CEUX-CI
  申请人：GLAXO GROUP LTD

  公开号：WO2004099198A1

  公开（公告）日：2004-11-18

  Benzoxazinone derivatives, their preparation and use Compounds of formula (I) and pharmaceutically acceptable salts thereof are disclosed: (I) wherein R1 is hydrogen or C1-6alkyl; R2 is fluoro or chloro; R3 is hydrogen, fluoro or chloro; and X is nitrogen or CH. Methods of preparation and uses thereof in treatment of CNS disorders, such as depression or anxiety, are also disclosed.

  苯并噁唑酮衍生物，它们的制备和用途是公开的：其中R1是氢或C1-6烷基；R2是氟或氯；R3是氢、氟或氯；X是氮或CH。还公开了其制备方法和在治疗中枢神经系统疾病，如抑郁症或焦虑症中的用途。
• 3,4-Dihydro-2H-benzoxazinones as dual-acting 5-HT1A receptor antagonists and serotonin reuptake inhibitors
  作者：Peter J. Lovell、Frank E. Blaney、Caroline J. Goodacre、Claire M. Scott、Paul W. Smith、Kathryn R. Starr、Kevin M. Thewlis、Antonio K.K. Vong、Simon E. Ward、Jeannette M. Watson

  DOI：10.1016/j.bmcl.2006.11.031

  日期：2007.2

  Investigation of halogen substitution in lead compound 1 has led to the identification of analogues which combine high affinity for 5-HT1A receptors and potent serotonin reuptake inhibitory activity. Several compounds show an improved selectivity over 5-HT1B and 5-HT1D receptors and a superior pharmacokinetic profile in the rat. (c) 2006 Elsevier Ltd. All rights reserved.