1-(2,2,2-trichloroethoxy)carbonyl-2-phenylethynyl-4-oxo-1,2,3,4-tetrahydropyridine | 818377-53-6

• 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: 1-(2,2,2-trichloroethoxy)carbonyl-2-phenylethynyl-4-oxo-1,2,3,4-tetrahydropyridine
• 英文别名: 2,2,2-Trichloroethyl 4-oxo-2-(2-phenylethynyl)-2,3-dihydropyridine-1-carboxylate
• CAS: 818377-53-6
• 化学式: C₁₆H₁₂Cl₃NO₃
• 分子量: 372.635
• InChiKey: AIMOZPGPDBMVLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2,2,2-trichloroethoxy)carbonyl-2-phenylethynyl-4-oxo-1,2,3,4-tetrahydropyridine 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以94%的产率得到1-(2,2,2-trichloroethoxy)carbonyl-2-phenethyl-4-oxo-1,2,3,4-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：

  、 苯乙炔 在 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以2.62 g的产率得到1-(2,2,2-trichloroethoxy)carbonyl-2-phenylethynyl-4-oxo-1,2,3,4-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

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.