methyl 2-(trifluoromethylsulfonyloxy)-5-(dipropylamino)cyclohex-1-ene-1-carboxylate | 859456-20-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: methyl 2-(trifluoromethylsulfonyloxy)-5-(dipropylamino)cyclohex-1-ene-1-carboxylate
• CAS: 859456-20-5
• 化学式: C₁₅H₂₄F₃NO₅S
• 分子量: 387.42
• InChiKey: BTRYDEZEWMVDRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2-(trifluoromethylsulfonyloxy)-5-(dipropylamino)cyclohex-1-ene-1-carboxylate 在 bis-triphenylphosphine-palladium(II) chloride 哌啶 、 manganese(IV) oxide 、 copper(l) iodide 、 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 66.25h， 生成 Dipropyl-(4-trimethylsilanylethynyl-3-vinyl-cyclohex-3-enyl)-amine
  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：

  4-di-n-propylaminocyclohexanone 在 potassium hydride 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 methyl 2-(trifluoromethylsulfonyloxy)-5-(dipropylamino)cyclohex-1-ene-1-carboxylate
  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