4-hydroxy-1-[4-oxo-4-(4-fluorophenyl)butyl]-4-[3-(trifluoromethyl)phenyl]-4-silapiperidinium chloride | 1219827-26-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxy-1-[4-oxo-4-(4-fluorophenyl)butyl]-4-[3-(trifluoromethyl)phenyl]-4-silapiperidinium chloride
• 英文别名: 1-(4-Fluorophenyl)-4-[4-hydroxy-4-[3-(trifluoromethyl)phenyl]-1,4-azasilinan-1-yl]butan-1-one;hydrochloride
• CAS: 1219827-26-5
• 化学式: C₂₁H₂₃F₄NO₂Si*ClH
• 分子量: 461.959
• InChiKey: NRVVRBWNQUCWTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-[3-(trifluoromethyl)phenyl]-1-{3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl}-4-(2,4,6-trimethoxyphenyl)-4-silapiperidine 在 盐酸 、 水 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以74%的产率得到4-hydroxy-1-[4-oxo-4-(4-fluorophenyl)butyl]-4-[3-(trifluoromethyl)phenyl]-4-silapiperidinium chloride
  参考文献：
  名称：

  Sila-Trifluperidol, a Silicon Analogue of the Dopamine (D₂) Receptor Antagonist Trifluperidol: Synthesis and Pharmacological Characterization

  摘要：

  Trifluperidol (2a) is a dopamine (1)2) receptor antagonist of the butyrophenone type. Carbon/silicon exchange (sila-substitution) in the 4-position of the piperidine ring of 2a (R3COH --> R3SiOH) results in sila-trifluperidol (2b). The silanol 21) was synthesized in a multistep synthesis, starting from triethoxy(vinyl)silane, and was isolated as the hydrochloride 2b.HCl. Compound 2b" HC1 was structurally characterized by single-crystal X-ray diffraction and solution NMR spectroscopy, and the stability of the silanol 2b in aqueous solutions at different pH values was studied by ESI-MS experiments. In addition, the pharmacological profiles of the C/Si analogues trifluperidol (2a) and sila-trifluperidol (2b) and of the related compounds haloperidol (la) and sila-haloperidol (lb) were studied in functional receptor assays at human dopamine DI and D, receptors. Sila-substitution of la ( lb) and 2a ( 2b) affects the pharmacological properties significantly.

  DOI：

  10.1021/om901011t

文献信息

• Sila-Trifluperidol, a Silicon Analogue of the Dopamine (D₂) Receptor Antagonist Trifluperidol: Synthesis and Pharmacological Characterization
  作者：Reinhold Tacke、Binh Nguyen、Christian Burschka、W. Peter Lippert、Alexandra Hamacher、Christian Urban、Matthias U. Kassack

  DOI：10.1021/om901011t

  日期：2010.4.12

  Trifluperidol (2a) is a dopamine (1)2) receptor antagonist of the butyrophenone type. Carbon/silicon exchange (sila-substitution) in the 4-position of the piperidine ring of 2a (R3COH --> R3SiOH) results in sila-trifluperidol (2b). The silanol 21) was synthesized in a multistep synthesis, starting from triethoxy(vinyl)silane, and was isolated as the hydrochloride 2b.HCl. Compound 2b" HC1 was structurally characterized by single-crystal X-ray diffraction and solution NMR spectroscopy, and the stability of the silanol 2b in aqueous solutions at different pH values was studied by ESI-MS experiments. In addition, the pharmacological profiles of the C/Si analogues trifluperidol (2a) and sila-trifluperidol (2b) and of the related compounds haloperidol (la) and sila-haloperidol (lb) were studied in functional receptor assays at human dopamine DI and D, receptors. Sila-substitution of la ( lb) and 2a ( 2b) affects the pharmacological properties significantly.