diethoxy[3-(trifluoromethyl)phenyl]vinylsilane | 1219827-20-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethoxy[3-(trifluoromethyl)phenyl]vinylsilane
• 英文别名: Ethenyl-diethoxy-[3-(trifluoromethyl)phenyl]silane；ethenyl-diethoxy-[3-(trifluoromethyl)phenyl]silane
• CAS: 1219827-20-9
• 化学式: C₁₃H₁₇F₃O₂Si
• 分子量: 290.357
• InChiKey: MJDUZBFXRLPXSN-UHFFFAOYSA-N

物化性质

• 沸点：
  283.3±40.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3,5-三甲氧基苯 、 diethoxy[3-(trifluoromethyl)phenyl]vinylsilane 在 正丁基锂 、 四甲基乙二胺 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 16.17h， 以70%的产率得到ethoxy[3-(trifluoromethyl)phenyl](2,4,6-trimethoxyphenyl)vinylsilane
  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
• 作为产物：
  描述：

  间溴三氟甲苯 、 乙烯基三乙氧基硅烷 在 magnesium 作用下， 以 乙醚 为溶剂， 以84%的产率得到diethoxy[3-(trifluoromethyl)phenyl]vinylsilane
  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.