dimethoxy(phenyl)(3-piperidinopropyl)silane | 172166-66-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: dimethoxy(phenyl)(3-piperidinopropyl)silane
• CAS: 172166-66-4
• 化学式: C₁₆H₂₇NO₂Si
• 分子量: 293.481
• InChiKey: VRSAWNBFYTULRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  dimethoxy(phenyl)(3-piperidinopropyl)silane 在 盐酸 、 正丁基锂 作用下， 以 异丙醇 为溶剂， 反应 32.5h， 生成 p-fluoro-sila-difenidol
  参考文献：
  名称：

  Fluorine-containing derivatives of the muscarinic antagonists sila-pridinol and sila-difenidol: Syntheses and antimuscarinic properties

  摘要：

  The fluorine-containing sila-pridinol and sila-difenidol derivatives p-fluoro-sila-pridinol (5a), p,p'-difluoro-sila-pridinol (6a), p-fluoro-sila-difenidol (7a), p,p'-difluoro-sila-difenidol (8a), p-fluoro-sila-difenidol methiodide (9a) and p,p'-difluoro-sila-difenidol methiodide (10a) were synthesized, starting from the silanes Cl3SiCH=CH2 (5a and 6a) and (CH3O)(3)Si(CH2)(3)Cl(7a-10a) respectively. The chiral compounds 5a, 7a and 9a were obtained as racemic mixtures: The muscarinic pharmacology of the silanols 5a-10a was studied and compared with that of their carbon analogues, the carbinols 5b-10b (studies on silicon-carbon bioisosterism). The affinities and receptor selectivities (M1-M4 receptors) of the Si-C pairs 5a/5b-10a/10b were found to depend on the following structural parameters: length of the carbon chain El-(CH2)(n)-N(El = Si or C; n = 2, 3), N-methylation, fluorine substitution of the phenyl rings and the nature of the central atom (silicon or carbon). Most interestingly, replacement of the central carbinol carbon atom in p-fluoro-difenidol methiodide (9b) by a silicon atom (--> 9a) leads to an increase in affinity for muscarinic receptor subtypes by factors of 32-81. Such a high increase in biological activity by sila-substitution (C-Si exchange) has not yet been reported.

  DOI：

  10.1016/0022-328x(95)05622-v
• 作为产物：
  描述：

  3-氯丙基三甲氧基硅烷 在 magnesium 作用下， 以 甲醇 为溶剂， 反应 36.0h， 生成 dimethoxy(phenyl)(3-piperidinopropyl)silane
  参考文献：
  名称：

  Fluorine-containing derivatives of the muscarinic antagonists sila-pridinol and sila-difenidol: Syntheses and antimuscarinic properties

  摘要：

  The fluorine-containing sila-pridinol and sila-difenidol derivatives p-fluoro-sila-pridinol (5a), p,p'-difluoro-sila-pridinol (6a), p-fluoro-sila-difenidol (7a), p,p'-difluoro-sila-difenidol (8a), p-fluoro-sila-difenidol methiodide (9a) and p,p'-difluoro-sila-difenidol methiodide (10a) were synthesized, starting from the silanes Cl3SiCH=CH2 (5a and 6a) and (CH3O)(3)Si(CH2)(3)Cl(7a-10a) respectively. The chiral compounds 5a, 7a and 9a were obtained as racemic mixtures: The muscarinic pharmacology of the silanols 5a-10a was studied and compared with that of their carbon analogues, the carbinols 5b-10b (studies on silicon-carbon bioisosterism). The affinities and receptor selectivities (M1-M4 receptors) of the Si-C pairs 5a/5b-10a/10b were found to depend on the following structural parameters: length of the carbon chain El-(CH2)(n)-N(El = Si or C; n = 2, 3), N-methylation, fluorine substitution of the phenyl rings and the nature of the central atom (silicon or carbon). Most interestingly, replacement of the central carbinol carbon atom in p-fluoro-difenidol methiodide (9b) by a silicon atom (--> 9a) leads to an increase in affinity for muscarinic receptor subtypes by factors of 32-81. Such a high increase in biological activity by sila-substitution (C-Si exchange) has not yet been reported.

  DOI：

  10.1016/0022-328x(95)05622-v