Tert-butyl 4-[2-(6-chloro-2-iodopyridin-3-yl)oxyethylidene]piperidine-1-carboxylate | 666178-94-5

• 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: Tert-butyl 4-[2-(6-chloro-2-iodopyridin-3-yl)oxyethylidene]piperidine-1-carboxylate
• 英文别名: tert-butyl 4-[2-(6-chloro-2-iodopyridin-3-yl)oxyethylidene]piperidine-1-carboxylate
• CAS: 666178-94-5
• 化学式: C₁₇H₂₂ClIN₂O₃
• 分子量: 464.731
• InChiKey: REGCAISTFBBPSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Tert-butyl 4-[2-(6-chloro-2-iodopyridin-3-yl)oxyethylidene]piperidine-1-carboxylate 在 sodium formate palladium diacetate 、 n-Bu₄Cl 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以60%的产率得到4-(5-Chloro-furo[3,2-b]pyridin-3-yl)-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Substituted furo[3,2-b]pyridines: novel bioisosteres of 5-HT1F receptor agonists

  摘要：

  Synthesis and evaluation of a series of 2,3,5- and 3,5-substituted furo[3,2-b]pyridines were undertaken in order to investigate their utility as bioisosteres of 5-HTIF receptor agonist indole analogues, 1-3. The replacement proved to be effective, providing compounds with similar 5-HTIF receptor affinity and improved selectivity when compared with the indole analogues. Through these studies we identified 4-fluoro-N-[3-(1-methyl-piperidin-4-yl)-furo[3,2-b]pyridin-5-yl]-benzamide (5), a potent and selective 5-HTIF receptor agonist with the potential to treat acute migraine. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.091
• 作为产物：
  描述：

  叔丁基 4-(2-乙氧基-2-氧代亚乙基)哌啶-1-羧酸 在 lithium aluminium tetrahydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 生成 Tert-butyl 4-[2-(6-chloro-2-iodopyridin-3-yl)oxyethylidene]piperidine-1-carboxylate
  参考文献：
  名称：

  Substituted furo[3,2-b]pyridines: novel bioisosteres of 5-HT1F receptor agonists

  摘要：

  Synthesis and evaluation of a series of 2,3,5- and 3,5-substituted furo[3,2-b]pyridines were undertaken in order to investigate their utility as bioisosteres of 5-HTIF receptor agonist indole analogues, 1-3. The replacement proved to be effective, providing compounds with similar 5-HTIF receptor affinity and improved selectivity when compared with the indole analogues. Through these studies we identified 4-fluoro-N-[3-(1-methyl-piperidin-4-yl)-furo[3,2-b]pyridin-5-yl]-benzamide (5), a potent and selective 5-HTIF receptor agonist with the potential to treat acute migraine. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.091