5-Dipropylamino-2-ethynyl-cyclohex-1-enecarboxylic acid methyl ester | 859456-47-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基酰胺
• 英文名称: 5-Dipropylamino-2-ethynyl-cyclohex-1-enecarboxylic acid methyl ester
• CAS: 859456-47-6
• 化学式: C₁₆H₂₅NO₂
• 分子量: 263.38
• InChiKey: RKRPEDWCFAYATH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-Dipropylamino-2-ethynyl-cyclohex-1-enecarboxylic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.75h， 生成 [2-ethynyl-5-(dipropylamino)cyclohex-1-en-1-yl]methanol
  参考文献：
  名称：

  Fancy bioisosteres: Synthesis, SAR, and pharmacological investigations of novel nonaromatic dopamine D3 receptor ligands

  摘要：

  Structural variations of the lead compound FAUC 88 led to dopaminergic enynes with an extended pi-system when Pd-catalyzed cross coupling reactions were employed for the key reaction steps. The dienyne 9b displayed substantial affinity for the dopamine receptor subtype D3 and remarkable selectivity over D4. Compared to FAUC 88, the novel fancy bioisostere 9b displayed reduced ligand efficacy. DFT-based conformational analysis of the test compound 9b, including the calculation of diagnostic magnetic shielding properties and their comparison with experimentally derived NMR data, indicated a clear energetic preference for the s-trans geometry of the diene substructure. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.047
• 作为产物：
  描述：

  methyl 2-(trifluoromethylsulfonyloxy)-5-(dipropylamino)cyclohex-1-ene-1-carboxylate 在 bis-triphenylphosphine-palladium(II) chloride 哌啶 、 copper(l) iodide 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.67h， 生成 5-Dipropylamino-2-ethynyl-cyclohex-1-enecarboxylic acid methyl ester
  参考文献：
  名称：

  Fancy bioisosteres: Synthesis, SAR, and pharmacological investigations of novel nonaromatic dopamine D3 receptor ligands

  摘要：

  Structural variations of the lead compound FAUC 88 led to dopaminergic enynes with an extended pi-system when Pd-catalyzed cross coupling reactions were employed for the key reaction steps. The dienyne 9b displayed substantial affinity for the dopamine receptor subtype D3 and remarkable selectivity over D4. Compared to FAUC 88, the novel fancy bioisostere 9b displayed reduced ligand efficacy. DFT-based conformational analysis of the test compound 9b, including the calculation of diagnostic magnetic shielding properties and their comparison with experimentally derived NMR data, indicated a clear energetic preference for the s-trans geometry of the diene substructure. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.047