cyclohexyldimethoxy(3-piperidinopropyl)silane | 137933-42-7

• 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: cyclohexyldimethoxy(3-piperidinopropyl)silane
• 英文别名: cyclohexyl-dimethoxy-(3-piperidin-1-ylpropyl)silane
• CAS: 137933-42-7
• 化学式: C₁₆H₃₃NO₂Si
• 分子量: 299.529
• InChiKey: YZFWKTBEXSSETL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cyclohexyldimethoxy(3-piperidinopropyl)silane 在 氢氧化钾 、 lithium aluminium tetrahydride 、 正丁基锂 作用下， 以 乙醇 、 二丁醚 、 水 为溶剂， 反应 58.0h， 生成 对氟-六氢-硅杂-地芬尼多
  参考文献：
  名称：

  Cyclohexy (4-fluorophenyl)(3-piperidinopropyl)silanol ((itp)-fluoro-hexahydro-sila-difenidol, p-F-HSSiD) and derivatives: synthesis and antimuscarinic properties

  摘要：

  Four different syntheses of the potent and selective muscarinic antagonist cyclohexyl(4-fluorophenyl)(3-piperidinopropyl)silanol (p-fluoro-hexahydro-sila-difenidol, p-F-HHSiD (2b); isolated as hydrochloride 2b.HCl) are described (starting materials: (CH3O)3SiCH2CH2CH2Cl and Si(OCH3)4). In addition, the synthesis of the corresponding carbon analogue p-fluoro-hexahydro-difenidol (p-F-HHD (2a); isolated as 2a.HCl) and the syntheses of three p-F-HHSiD derivatives (3-5), with a modified cyclic amino group, are reported (3: piperidino/pyrrolidino exchange, isolated as 3.HCl; 4: piperidino/hexamethylenimino exchange, isolated as 4.HCl; 5: quaternization of 2b with methyl iodide). The chiral compounds 2a, 2b, 3, 4 and 5 were prepared as racemates. In functional pharmacological studies, 3-5 behaved as simple competitive antagonists at muscarinic M1 receptors in rabbit vas deferens, M2 receptors in guinea-pig atria, and M3 receptors in guinea-pig ileal smooth muscle. The pyrrolidino (3) and hexamethylenimino (4) analogues of the parent drug p-F-HHSiD (2b) displayed the highest affinity for M1 and M3 receptors (pA2 values: 7.0-7.4) but exhibited lower affinity for cardiac M2 receptors (pA2: 5.9 and 6.0). Their affinity profile (M1 approximately M3 > M2) is different from that of p-F-HHSiD (2b) (M3 > M1 > M2), but qualitatively very similar to that of p-F-HHD (2a). The methiodide 5 exhibited the highest affinity for M1 receptors (pA2: 8.5) but lower affinity for M2 and M3 receptors by factors of 5.6 and 3.6, respectively.

  DOI：

  10.1016/0022-328x(91)80194-o
• 作为产物：
  描述：

  哌啶 、 3-氯丙基-环己基-二甲氧基硅烷 以 甲醇 为溶剂， 反应 16.0h， 以88%的产率得到cyclohexyldimethoxy(3-piperidinopropyl)silane
  参考文献：
  名称：

  Cyclohexy (4-fluorophenyl)(3-piperidinopropyl)silanol ((itp)-fluoro-hexahydro-sila-difenidol, p-F-HSSiD) and derivatives: synthesis and antimuscarinic properties

  摘要：

  Four different syntheses of the potent and selective muscarinic antagonist cyclohexyl(4-fluorophenyl)(3-piperidinopropyl)silanol (p-fluoro-hexahydro-sila-difenidol, p-F-HHSiD (2b); isolated as hydrochloride 2b.HCl) are described (starting materials: (CH3O)3SiCH2CH2CH2Cl and Si(OCH3)4). In addition, the synthesis of the corresponding carbon analogue p-fluoro-hexahydro-difenidol (p-F-HHD (2a); isolated as 2a.HCl) and the syntheses of three p-F-HHSiD derivatives (3-5), with a modified cyclic amino group, are reported (3: piperidino/pyrrolidino exchange, isolated as 3.HCl; 4: piperidino/hexamethylenimino exchange, isolated as 4.HCl; 5: quaternization of 2b with methyl iodide). The chiral compounds 2a, 2b, 3, 4 and 5 were prepared as racemates. In functional pharmacological studies, 3-5 behaved as simple competitive antagonists at muscarinic M1 receptors in rabbit vas deferens, M2 receptors in guinea-pig atria, and M3 receptors in guinea-pig ileal smooth muscle. The pyrrolidino (3) and hexamethylenimino (4) analogues of the parent drug p-F-HHSiD (2b) displayed the highest affinity for M1 and M3 receptors (pA2 values: 7.0-7.4) but exhibited lower affinity for cardiac M2 receptors (pA2: 5.9 and 6.0). Their affinity profile (M1 approximately M3 > M2) is different from that of p-F-HHSiD (2b) (M3 > M1 > M2), but qualitatively very similar to that of p-F-HHD (2a). The methiodide 5 exhibited the highest affinity for M1 receptors (pA2: 8.5) but lower affinity for M2 and M3 receptors by factors of 5.6 and 3.6, respectively.

  DOI：

  10.1016/0022-328x(91)80194-o