4-benzyloxy-2,6-diphenethylpyridine | 1174132-10-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-benzyloxy-2,6-diphenethylpyridine
• 英文别名: 2,6-Bis(2-phenylethyl)-4-phenylmethoxypyridine
• CAS: 1174132-10-5
• 化学式: C₂₈H₂₇NO
• 分子量: 393.528
• InChiKey: NPXLIKUUCFPNPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-benzyloxy-2,6-diphenethylpyridine 以 4-甲基-2-戊醇 为溶剂， 反应 4.0h， 以100%的产率得到2,6-diphenethylpyridin-4-ol
  参考文献：
  名称：

  Stereocontrolled Synthesis and Pharmacological Evaluation ofcis-2,6-Diphenethyl-1-azabicyclo[2.2.2]octanes as Lobelane Analogues

  摘要：

  An efficient and highly stereocontrolled approach for the synthesis of the quinuclidine incorporated lobelane analogues, endo,endo-and exo,exo-2,6-cis-diphenethyl-1-azabicyclo-[2.2.2]octane (2 and 3), has been developed. Analogue; 2 and 3 were designed to mimic the axial and equatorial geometry, respectively, of the vesicular monoamine transporter-2 (VMAT2) inhibitor, lobelane. The exo,exo analogue 2 had comparable affinity to lobelane and had greater affinity than the endo,endo analogue 3 at the tetrabenazine binding site on VMAT2, indicating that the preferred binding mode of lobelane is likely the extended conformation.

  DOI：

  10.1021/jo901082r
• 作为产物：
  描述：

  2,6-diphenethylpyridin-4-ol 、 溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以87%的产率得到4-benzyloxy-2,6-diphenethylpyridine
  参考文献：
  名称：

  Stereocontrolled Synthesis and Pharmacological Evaluation ofcis-2,6-Diphenethyl-1-azabicyclo[2.2.2]octanes as Lobelane Analogues

  摘要：

  An efficient and highly stereocontrolled approach for the synthesis of the quinuclidine incorporated lobelane analogues, endo,endo-and exo,exo-2,6-cis-diphenethyl-1-azabicyclo-[2.2.2]octane (2 and 3), has been developed. Analogue; 2 and 3 were designed to mimic the axial and equatorial geometry, respectively, of the vesicular monoamine transporter-2 (VMAT2) inhibitor, lobelane. The exo,exo analogue 2 had comparable affinity to lobelane and had greater affinity than the endo,endo analogue 3 at the tetrabenazine binding site on VMAT2, indicating that the preferred binding mode of lobelane is likely the extended conformation.

  DOI：

  10.1021/jo901082r

文献信息

• Stereocontrolled Synthesis and Pharmacological Evaluation of<i>cis</i>-2,6-Diphenethyl-1-azabicyclo[2.2.2]octanes as Lobelane Analogues
  作者：Guangrong Zheng、Linda P. Dwoskin、Agripina G. Deaciuc、Peter A. Crooks

  DOI：10.1021/jo901082r

  日期：2009.8.21

  An efficient and highly stereocontrolled approach for the synthesis of the quinuclidine incorporated lobelane analogues, endo,endo-and exo,exo-2,6-cis-diphenethyl-1-azabicyclo-[2.2.2]octane (2 and 3), has been developed. Analogue; 2 and 3 were designed to mimic the axial and equatorial geometry, respectively, of the vesicular monoamine transporter-2 (VMAT2) inhibitor, lobelane. The exo,exo analogue 2 had comparable affinity to lobelane and had greater affinity than the endo,endo analogue 3 at the tetrabenazine binding site on VMAT2, indicating that the preferred binding mode of lobelane is likely the extended conformation.