tert-butyl 3-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.1.1]heptane-6-carboxylate | 1097062-18-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: tert-butyl 3-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.1.1]heptane-6-carboxylate
• CAS: 1097062-18-4
• 化学式: C₁₅H₂₀ClN₃O₂
• 分子量: 309.796
• InChiKey: WVDJIUSUGSUYNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  45.67
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.1.1]heptane-6-carboxylate 在 甲酸 作用下， 反应 3.5h， 以81%的产率得到3-(6-Chloropyridin-3-yl)-3,6-diazabicyclo[3.1.1]heptane
  参考文献：
  名称：

  Synthesis of 3,6-diazabicyclo[3.1.1]heptanes as novel ligands for neuronal nicotinic acetylcholine receptors

  摘要：

  F series of novel 3,6-diazabicyclo[3.1.1] heptane derivatives 4a -f was synthesized and their affinity and selectivity towards alpha 4 beta 2 and alpha 7 nAChR subtypes were evaluated. The results of the current study revealed a number of compounds (4a, 4b and 4c) having a very high affinity for alpha 4 beta 2 (Ki at alpha 4 beta 2 ranging from 0.023 to 0.056 nM) versus alpha 7 nAChR subtypes; among these compounds, the 3-(6-bromopyridin-3-yl)- 3,6-diazabicyclo[3.1.1] heptane 4c was found to be the most alpha 7 alpha 4 beta 2 selective term in receptor binding assays (alpha 7 alpha 4 beta 2 = 1295). Moreover, compound 4d also had high affinity for the a4b2 nAChR subtype (K-i = 1.2 nM) with considerably high selectivity (alpha 7/alpha 4 beta 2 = 23300). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.002
• 作为产物：
  描述：

  2-氯-5-碘吡啶 、 3,6-二氮杂双环[3.1.1]庚烷-6-羧酸叔丁酯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 22.0h， 以66%的产率得到tert-butyl 3-(6-chloropyridin-3-yl)-3,6-diazabicyclo[3.1.1]heptane-6-carboxylate
  参考文献：
  名称：

  Synthesis of 3,6-diazabicyclo[3.1.1]heptanes as novel ligands for neuronal nicotinic acetylcholine receptors

  摘要：

  F series of novel 3,6-diazabicyclo[3.1.1] heptane derivatives 4a -f was synthesized and their affinity and selectivity towards alpha 4 beta 2 and alpha 7 nAChR subtypes were evaluated. The results of the current study revealed a number of compounds (4a, 4b and 4c) having a very high affinity for alpha 4 beta 2 (Ki at alpha 4 beta 2 ranging from 0.023 to 0.056 nM) versus alpha 7 nAChR subtypes; among these compounds, the 3-(6-bromopyridin-3-yl)- 3,6-diazabicyclo[3.1.1] heptane 4c was found to be the most alpha 7 alpha 4 beta 2 selective term in receptor binding assays (alpha 7 alpha 4 beta 2 = 1295). Moreover, compound 4d also had high affinity for the a4b2 nAChR subtype (K-i = 1.2 nM) with considerably high selectivity (alpha 7/alpha 4 beta 2 = 23300). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.002