N-butoxycarbonyl-3-hydroxy-3-(2-pyrimidinyl)piperidine | 182416-10-0

• 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: N-butoxycarbonyl-3-hydroxy-3-(2-pyrimidinyl)piperidine
• 英文别名: N-t-butoxycarbonyl-3-hydroxy-3-(2-pyrimidinyl)piperidine；tert-butyl 3-hydroxy-3-pyrimidin-2-ylpiperidine-1-carboxylate
• CAS: 182416-10-0
• 化学式: C₁₄H₂₁N₃O₃
• 分子量: 279.339
• InChiKey: PVHQACRKHVVNRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-butoxycarbonyl-3-hydroxy-3-(2-pyrimidinyl)piperidine 在 吡啶 、 三氟乙酸 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 生成 3-(2-pyrimidinyl)-1,2,5,6-tetrahydropyridine
  参考文献：
  名称：

  New piperidinyl- and 1,2,3,6-tetrahydropyridinyl-pyrimidine derivatives as selective 5-HT1A receptor agonists with highly potent anti-ischemic effects

  摘要：

  A series of new piperidinyl- and 1,2,3,6-tetrahydropyridinyl-pyrimidine derivatives were synthesized. Among these compounds, 4-methyl-2-(1,2,3,6-tetrahydropyridin-4-yl)pyrimidine derivative 23 (SUN N5147) exhibited sub-nanomolar affinity for 5-HT1A receptor with 1000-fold selectivity over both dopamine D-2 and alpha(1)-adrenergic receptors and remarkable neuroprotective activity in a transient middle cerebral artery occlusion (t-MCAO) model. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.04.059
• 作为产物：
  描述：

  N-叔丁氧羰基-3-哌啶酮 、 2-(三丁基锡)嘧啶 在 正丁基锂 、 ammonium chloride 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 为溶剂， 以29%的产率得到N-butoxycarbonyl-3-hydroxy-3-(2-pyrimidinyl)piperidine
  参考文献：
  名称：

  Benzoxazepine derivatives and their salts and medicaments containing the same

  摘要：

  一种具有通式（I）的苯并噁唑啉衍生物及其盐和含有相同有效成分的药物： 其中，n为2至5的整数，R1表示氢原子、卤原子、C1至C4的低碳基团、C1至C4的低碳氧基碳基团、C1至C4的卤代烷基团、氰基或酯基，R2表示氢原子、卤原子、C1至C4的低碳基团、C1至C4的低碳氧基团或羟基，虚线表示结合键的存在或缺失，W表示C、CH或CH2或氮原子，但当W为氮原子时，Z与W结合，虚线表示缺少结合，Z表示未取代或取代的芳香烃环基团或未取代或取代的杂环基团）。 这种苯并噁唑啉衍生物及其盐可用作治疗焦虑神经症、恐惧症、强迫症、精神分裂症、心脏创伤后应激、抑郁症、心身疾病和其他精神神经病性障碍、进食障碍、更年期障碍、婴儿孤独症以及伴有脑梗死和脑出血的脑循环系统紊乱或呕吐症的药物。

  公开号：

  US06187769B1

文献信息

• Pyrimidine derivatives and their salts, useful for making benzoxazepine derivatives
  申请人：Suntory Limited

  公开号：US06337397B1

  公开（公告）日：2002-01-08

  A benzoxazepine derivative having the general formula (I) and its salts and medicaments containing the same as effective ingredients: wherein, n is an integer of 2 to 5, R1 indicates a hydrogen atom, halogen atom, C1 to C4 lower alkyl group, C1 to C4 lower alkoxyalkyl group, C1 to C4 halogenoalkyl group, cyano group, or ester group, R2 indicates a hydrogen atom, halogen atom, C1 to C4 lower alkyl group, C1 to C4 lower alkoxy group, or hydroxy group, a dotted line indicates the presence or absence of a binding bond, W indicates C, CH, or CH2 or a nitrogen atom, provided that, when W is a nitrogen atom, Z is bonded to W and the dotted line indicates the absence of a bond, and Z indicates an unsubstituted or substituted aromatic hydrocarbon ring group or an unsubstituted or substituted heterocyclic group).

  一种具有通式（I）的苯并噁唑啉衍生物及其盐和含有其作为有效成分的药物： 其中，n为2至5的整数，R1表示氢原子、卤原子、C1至C4的低碳基团、C1至C4的低碳氧基碳基团、C1至C4的卤代烷基团、氰基或酯基，R2表示氢原子、卤原子、C1至C4的低碳基团、C1至C4的低碳氧基团或羟基，虚线表示结合键的存在或缺失，W表示C、CH或CH2或氮原子，但当W为氮原子时，Z与W结合，虚线表示缺少结合，Z表示未取代或取代的芳香烃环基团或未取代或取代的杂环基团。
• Synthesis, SAR studies, and evaluation of 1,4-benzoxazepine derivatives as selective 5-HT1A receptor agonists with neuroprotective effect: Discovery of Piclozotan
  作者：Katsuhide Kamei、Noriko Maeda、Kayoko Nomura、Makoto Shibata、Ryoko Katsuragi-Ogino、Makoto Koyama、Mika Nakajima、Teruyoshi Inoue、Tomochika Ohno、Toshio Tatsuoka

  DOI：10.1016/j.bmc.2005.10.046

  日期：2006.3

  A new series of 1,4-benzoxazepine derivatives was designed, synthesized, and evaluated for binding to 5-HT1A receptor and cerebral anti-ischemic effect. A lot of compounds exhibited nanomolar affinity for 5-HT1A receptor with good selectivity over both dopamine D, and alpha(1)-adrenergic receptors. Among these compounds, 3-chloro-4-[4-[4-(2-pyridinyl)-1,2,3,6-tetrahydropyridin-1-y]butyl]-1, 4-benzoxazepin-5(4H)-one (50: SUN N4057 (Piclozotan) as 2HCl salt) showed remarkable neuroprotective activity in a transient middle cerebral artery occlusion (t-MCAO) model. (c) 2005 Elsevier Ltd. All rights reserved.
• US6114522
  申请人：——

  公开号：——

  公开（公告）日：——
• PROCESS OF PRODUCTION OF 4-SUBSTITUTED-3-HALOGENO-1,4-BENZOXAZEPINE DERIVATIVE AND SALTS THEREOF
  申请人：SUNTORY LIMITED

  公开号：EP0925288B1

  公开（公告）日：2002-09-25
• BENZOXAZEPINE DERIVATIVES, SALTS THEREOF, AND DRUGS CONTAINING THE SAME
  申请人：SUNTORY LIMITED

  公开号：EP0755930B1

  公开（公告）日：2002-07-31