N-benzyl-4-benzyloxy-2,6-diphenethylpyridinium bromide | 1174132-11-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-benzyl-4-benzyloxy-2,6-diphenethylpyridinium bromide
• 英文别名: 1-Benzyl-2,6-bis(2-phenylethyl)-4-phenylmethoxypyridin-1-ium;bromide
• CAS: 1174132-11-6
• 化学式: Br*C₃₅H₃₄NO
• 分子量: 564.565
• InChiKey: OBDPBZPSPLAPLH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.18
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-4-benzyloxy-2,6-diphenethylpyridinium bromide 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以89%的产率得到cis-N-benzyl-4-benzyloxy-2,6-diphenethyl-1,2,5,6-tetrahydropyridine
  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：

  4-benzyloxy-2,6-diphenethylpyridine 、 溴甲苯 以 乙腈 为溶剂， 反应 96.0h， 以36%的产率得到N-benzyl-4-benzyloxy-2,6-diphenethylpyridinium bromide
  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.