2,6-bis((p-tolyloxy)methyl)pyridine | 1428797-45-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,6-bis((p-tolyloxy)methyl)pyridine
• 英文别名: 2,6-Bis[(4-methylphenoxy)methyl]pyridine
• CAS: 1428797-45-8
• 化学式: C₂₁H₂₁NO₂
• 分子量: 319.403
• InChiKey: BIUUHOWLLLOOOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-bis((p-tolyloxy)methyl)pyridine 在 ammonia borane 、 三(五氟苯基)硼烷 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以80%的产率得到cis-2,6-bis((p-tolyloxy)methyl)piperidine
  参考文献：
  名称：

  硼烷与氨硼烷的硼烷催化的吡啶加氢转移

  摘要：

  通过使用氨硼烷作为氢源，首次成功实现了硼烷催化的吡啶的无金属转移加氢，以44-88％的产率提供了中等至优异的顺式选择性的各种哌啶。不需要高压H 2的容易处理使得该转移氢化实用且有用。

  DOI：

  10.1021/acs.orglett.6b02610
• 作为产物：
  描述：

  2,6-双(溴甲基)吡啶 、 对甲酚 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以92%的产率得到2,6-bis((p-tolyloxy)methyl)pyridine
  参考文献：
  名称：

  Strategies To Reduce hERG K⁺Channel Blockade. Exploring Heteroaromaticity and Rigidity in Novel Pyridine Analogues of Dofetilide

  摘要：

  Drug-induced blockade of the human ether-a-go-go-related gene K+ channel (hERG) represents one of the major antitarget concerns in pharmaceutical industry. SAR studies of this ion channel have shed light on the structural requirements for hERG interaction but most importantly may reveal drug design principles to reduce hERG affinity. In the present study, a novel library of neutral and positively charged heteroaromatic derivatives of the class III antiarrhythmic agent dofetilide was synthesized and assessed for hERG affinity in radioligand binding and manual patch clamp assays. Structural modifications of the pyridine moiety, side chain, and peripheral aromatic moieties were evaluated, thereby revealing approaches for reducing hERG binding affinity. In particular, we found that the extra rigidity imposed close to the positively charged pyridine moiety can be very efficient in decreasing hERG affinity.

  DOI：

  10.1021/jm301564f

文献信息

• Metal-Free Borane-Catalyzed Highly Stereoselective Hydrogenation of Pyridines
  作者：Yongbing Liu、Haifeng Du

  DOI：10.1021/ja406761j

  日期：2013.9.4

  A metal-free direct hydrogenation of pyridines was successfully realized by using homogeneous borane catalysts generated from alkenes and HB(C6F5)(2) via in situ hydroboration. The reaction affords a broad range of piperidines in high yields with excellent cis stereoselectivities.