2',6'-dichloro-[3,3']bipyridinyl-5-carboxylic acid ethyl ester | 1258604-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2',6'-dichloro-[3,3']bipyridinyl-5-carboxylic acid ethyl ester
• 英文别名: Ethyl 5-(2,6-dichloropyridin-3-yl)pyridine-3-carboxylate；ethyl 5-(2,6-dichloropyridin-3-yl)pyridine-3-carboxylate
• CAS: 1258604-48-6
• 化学式: C₁₃H₁₀Cl₂N₂O₂
• 分子量: 297.141
• InChiKey: NLDVATWJCYGSLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2',6'-dichloro-[3,3']bipyridinyl-5-carboxylic acid ethyl ester 、 4-甲氧基氯苄 在 potassium iodide 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以98%的产率得到
  参考文献：
  名称：

  Synthesis of a cytisine/epibatidine hybrid: a radical approach

  摘要：

  With the aim of developing a new ligand of neuronal nicotinic receptors (nAChRs) ionic and radical routes to the synthesis of a cytisine/epibatidine hybrid were studied The key step of the convergent synthesis was an unprecedented intramolecular coupling between a primary radical and a pyridine heterocycle The target compound 6 11-diaza was formed with its 4 11-diaza regioisomer (611 ''/411 '' 70/30) Both compounds exhibited a nanomolar affinity at the alpha(4)beta(2) nAChR subtype slightly better for the unexpected regioisomer [K-1 (nM) target compound and its regiolsomer 3 5 and 0 5 nM respectively] (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.09.079
• 作为产物：
  描述：

  5-溴烟酸乙酯 、 2,6-二氯-3-吡啶硼酸 在 1,1'-双(二苯基膦)二茂铁 、 palladium diacetate 、 cesium fluoride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 5.0h， 以29%的产率得到2',6'-dichloro-[3,3']bipyridinyl-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Synthesis of a cytisine/epibatidine hybrid: a radical approach

  摘要：

  With the aim of developing a new ligand of neuronal nicotinic receptors (nAChRs) ionic and radical routes to the synthesis of a cytisine/epibatidine hybrid were studied The key step of the convergent synthesis was an unprecedented intramolecular coupling between a primary radical and a pyridine heterocycle The target compound 6 11-diaza was formed with its 4 11-diaza regioisomer (611 ''/411 '' 70/30) Both compounds exhibited a nanomolar affinity at the alpha(4)beta(2) nAChR subtype slightly better for the unexpected regioisomer [K-1 (nM) target compound and its regiolsomer 3 5 and 0 5 nM respectively] (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tet.2010.09.079

文献信息

• Synthesis of a cytisine/epibatidine hybrid: a radical approach
  作者：Nicolas Houllier、Marie-Claire Lasne、Ronan Bureau、Pierre Lestage、Jacques Rouden

  DOI：10.1016/j.tet.2010.09.079

  日期：2010.11

  With the aim of developing a new ligand of neuronal nicotinic receptors (nAChRs) ionic and radical routes to the synthesis of a cytisine/epibatidine hybrid were studied The key step of the convergent synthesis was an unprecedented intramolecular coupling between a primary radical and a pyridine heterocycle The target compound 6 11-diaza was formed with its 4 11-diaza regioisomer (611 ''/411 '' 70/30) Both compounds exhibited a nanomolar affinity at the alpha(4)beta(2) nAChR subtype slightly better for the unexpected regioisomer [K-1 (nM) target compound and its regiolsomer 3 5 and 0 5 nM respectively] (C) 2010 Elsevier Ltd All rights reserved