[3-(trifluoromethyl)phenyl](2,4,6-trimethoxyphenyl)divinylsilane | 1219827-22-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [3-(trifluoromethyl)phenyl](2,4,6-trimethoxyphenyl)divinylsilane
• CAS: 1219827-22-1
• 化学式: C₂₀H₂₁F₃O₃Si
• 分子量: 394.466
• InChiKey: MVDPRYFWSJQLMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [3-(trifluoromethyl)phenyl](2,4,6-trimethoxyphenyl)divinylsilane 在 9-borabicyclo[3.3.1]nonane dimer 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 17.25h， 以67%的产率得到bis(2-hydroxyethyl)[3-(trifluoromethyl)phenyl]-(2,4,6-trimethoxyphenyl)silane
  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：

  ethoxy[3-(trifluoromethyl)phenyl](2,4,6-trimethoxyphenyl)vinylsilane 、 乙烯基氯化镁 以 四氢呋喃 为溶剂， 反应 1.17h， 以92%的产率得到[3-(trifluoromethyl)phenyl](2,4,6-trimethoxyphenyl)divinylsilane
  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