4-(3-fluoro-4-methoxy-5-nitro-benzylidene)-piperidine-1-carboxylic acid tert-butyl ester | 792936-57-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(3-fluoro-4-methoxy-5-nitro-benzylidene)-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 4-[(3-fluoro-4-methoxy-5-nitrophenyl)methylidene]piperidine-1-carboxylate；tert-butyl 4-[(3-fluoro-4-methoxy-5-nitrophenyl)methylidene]piperidine-1-carboxylate
• CAS: 792936-57-3
• 化学式: C₁₈H₂₃FN₂O₅
• 分子量: 366.389
• InChiKey: FRTYRXVMVKGYCY-UHFFFAOYSA-N

物化性质

• 沸点：
  498.7±45.0 °C(predicted)
• 密度：
  1.252±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(3-fluoro-4-methoxy-5-nitro-benzylidene)-piperidine-1-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 氢气 、 lithium chloride 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 6-(4-(N-(t-butyloxycarbonyl)piperidinyl)methyl)-8-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：

  3-氟-4-甲氧基苯甲醛 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 、 硝酸 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 4-(3-fluoro-4-methoxy-5-nitro-benzylidene)-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, THEIR PREPARATION AND USE<br/>[FR] DERIVES DE BENZOXAZINONE, PREPARATION ET UTILISATION ASSOCIEES
  申请人：GLAXO GROUP LTD

  公开号：WO2004099196A1

  公开（公告）日：2004-11-18

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

  公式（I）的化合物及其药用盐已被披露，其中R1是氢或C1-6烷基；R2是氟或氯。还披露了其制备方法以及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.