(3S,5R)-cis-2,2-dicyclohexyl-5-<(dimethylamino)methyl>-1,3-oxathiolane 3-oxide methiodide | 114882-87-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: (3S,5R)-cis-2,2-dicyclohexyl-5-<(dimethylamino)methyl>-1,3-oxathiolane 3-oxide methiodide
• 英文别名: [(3S,5R)-2,2-dicyclohexyl-3-oxo-1,3-oxathiolan-5-yl]methyl-trimethylazanium;iodide
• CAS: 114882-87-0
• 化学式: C₁₉H₃₆NO₂S*I
• 分子量: 469.471
• InChiKey: QTNMNMYCLZOFFQ-IMIWJGOWSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二环己基甲酮 在 dimethyl sulfide borane 、 双氧水 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醚 、 xylene 为溶剂， 反应 76.0h， 生成 (3S,5R)-cis-2,2-dicyclohexyl-5-<(dimethylamino)methyl>-1,3-oxathiolane 3-oxide methiodide
  参考文献：
  名称：

  Molecular requirements of the recognition site of cholinergic receptors. 27. Enantioselectivity of muscarinic antagonists. 2,2-Dicyclohexyl-5-[(dimethylamino)methyl]-1,3-oxathiolane methiodides and related 3-oxides

  摘要：

  The enantiomers of three chiral muscarinic antagonists carrying a 1,3-oxathiolane nucleus were prepared and their absolute configuration established. The enantioselectivity and tissue selectivity of such compounds were studied on rat bladder and guinea pig ileum and heart. The results show that introduction of a sulfoxide function brings about a small but definite enantioselectivity in the 1,3-oxathiolane compound (2), which in itself does not show enantioselectivity among the tissues studied. The results obtained point to differences among cardiac and ileal muscarinic receptors. Comparison of the absolute configuration related agonists shows that the most potent isomers of both series share the same absolute stereochemistry.

  DOI：

  10.1021/jm00117a006

文献信息

• ROMANELLI, M. NOVELLA;TEODORI, ELISABETTA;GUALTIERI, FULVIO;ANGELI, PIERO+, J. MED. CHEM., 31,(1988) N 9, C. 1698-1702
  作者：ROMANELLI, M. NOVELLA、TEODORI, ELISABETTA、GUALTIERI, FULVIO、ANGELI, PIERO+

  DOI：——

  日期：——
• Molecular requirements of the recognition site of cholinergic receptors. 27. Enantioselectivity of muscarinic antagonists. 2,2-Dicyclohexyl-5-[(dimethylamino)methyl]-1,3-oxathiolane methiodides and related 3-oxides
  作者：M. Novella Romanelli、Elisabetta Teodori、Fulvio Gualtieri、Piero Angeli、Livio Brasili

  DOI：10.1021/jm00117a006

  日期：1988.9

  The enantiomers of three chiral muscarinic antagonists carrying a 1,3-oxathiolane nucleus were prepared and their absolute configuration established. The enantioselectivity and tissue selectivity of such compounds were studied on rat bladder and guinea pig ileum and heart. The results show that introduction of a sulfoxide function brings about a small but definite enantioselectivity in the 1,3-oxathiolane compound (2), which in itself does not show enantioselectivity among the tissues studied. The results obtained point to differences among cardiac and ileal muscarinic receptors. Comparison of the absolute configuration related agonists shows that the most potent isomers of both series share the same absolute stereochemistry.