(E)-cyclohexyldimethoxy(3-piperidino-1-propen-1-yl)silane | 173951-22-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (E)-cyclohexyldimethoxy(3-piperidino-1-propen-1-yl)silane
• CAS: 173951-22-9
• 化学式: C₁₆H₃₁NO₂Si
• 分子量: 297.513
• InChiKey: QXEBHCGOVBKCLA-OQLLNIDSSA-N

物化性质

• 沸点：
  351.2±21.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  (E)-cyclohexyldimethoxy(3-piperidino-1-propen-1-yl)silane 在 盐酸 、 正丁基锂 作用下， 以 异丙醇 为溶剂， 反应 32.5h， 生成 (E)-1-<1--1-propen-3-yl>piperidine
  参考文献：
  名称：

  Unsaturated derivatives of the muscarinic antagonists hexahydro-sila-difenidol (HHSiD) and p-fluoro-hexahydro-sila-difenidol (p-F-HHSiD) with an (E)-SiCHCHCH2rmN moiety: Syntheses and binding affinities at muscarinic receptor subtypes

  摘要：

  The unsaturated HHSiD (1) and p-F-HHSiD (2) derivatives (E)-cyclohexyl(phenyl)(3-piperidino-1-propen-1-yl)silanol (5, isolated as 5 HCl) and (E)-cyclohexyl(4-fluorophenyl)(3-piperidino-1-propen-1-yl)silanol (6, isolated as 6 . HCl) were synthesized in four steps, starting from (CH3O)(3)SiH. Reaction of 5 and 6 with CH3Cl gave the corresponding methochlorides 7 and 8, respectively. All compounds were obtained as racemic mixtures. The binding affinities at muscarinic receptor subtypes (M1-M4) of the silanols 5-8 were determined and compared with those of the selective muscarinic antagonists 1 and 2 and their methiodides 3 and 4. These studies demonstrated that the ammonium compounds 3, 4, 7 and 8 display similar binding affinities at M1-M4 receptors and comparable receptor subtype selectivities. On the other hand, the conformationally restricted amines 5 and 6 ((E)-Si-CH=CH-CH2-N moiety) exhibit higher affinities but lower receptor subtype selectivities than the more flexible parent compounds 1 and 2 (Si-CH2-CH2-CH2-N moiety).

  DOI：

  10.1016/0022-328x(95)05584-7
• 作为产物：
  描述：

  1-(2-丙炔)哌啶 在 dihydrogen hexachloroplatinate 作用下， 以 乙醚 为溶剂， 反应 38.0h， 生成 (E)-cyclohexyldimethoxy(3-piperidino-1-propen-1-yl)silane
  参考文献：
  名称：

  Unsaturated derivatives of the muscarinic antagonists hexahydro-sila-difenidol (HHSiD) and p-fluoro-hexahydro-sila-difenidol (p-F-HHSiD) with an (E)-SiCHCHCH2rmN moiety: Syntheses and binding affinities at muscarinic receptor subtypes

  摘要：

  The unsaturated HHSiD (1) and p-F-HHSiD (2) derivatives (E)-cyclohexyl(phenyl)(3-piperidino-1-propen-1-yl)silanol (5, isolated as 5 HCl) and (E)-cyclohexyl(4-fluorophenyl)(3-piperidino-1-propen-1-yl)silanol (6, isolated as 6 . HCl) were synthesized in four steps, starting from (CH3O)(3)SiH. Reaction of 5 and 6 with CH3Cl gave the corresponding methochlorides 7 and 8, respectively. All compounds were obtained as racemic mixtures. The binding affinities at muscarinic receptor subtypes (M1-M4) of the silanols 5-8 were determined and compared with those of the selective muscarinic antagonists 1 and 2 and their methiodides 3 and 4. These studies demonstrated that the ammonium compounds 3, 4, 7 and 8 display similar binding affinities at M1-M4 receptors and comparable receptor subtype selectivities. On the other hand, the conformationally restricted amines 5 and 6 ((E)-Si-CH=CH-CH2-N moiety) exhibit higher affinities but lower receptor subtype selectivities than the more flexible parent compounds 1 and 2 (Si-CH2-CH2-CH2-N moiety).

  DOI：

  10.1016/0022-328x(95)05584-7