(2S,5S)-2-甲基-1,3-恶噻戊环-5-羧酸 | 103004-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧硫杂环戊烷
• 中文名称: (2S,5S)-2-甲基-1,3-恶噻戊环-5-羧酸
• 英文名称: cis-2-methyl-1,3-oxathiolane-5-carboxylic acid
• 英文别名: (2R,5R)-2-methyl-1,3-oxathiolane-5-carboxylic acid
• CAS: 103004-14-4
• 化学式: C₅H₈O₃S
• 分子量: 148.183
• InChiKey: HQLOYTAODDGJRH-DMTCNVIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  71.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  methyl (+/-)-cis-2-methyl-1,3-oxathiolane-5-carboxylate 在 sodium hydroxide 作用下， 反应 2.0h， 生成 (2S,5R)-2-甲基-1,3-恶噻戊环-5-羧酸 、 (2S,5S)-2-甲基-1,3-恶噻戊环-5-羧酸
  参考文献：
  名称：

  Molecular requirements of the recognition site of cholinergic receptors. 22. Resolution, absolute configuration, and cholinergic enantioselectivity of (+)- and (-)-cis-2-methyl-5-[(dimethylamino)methyl]-1,3-oxathiolane methiodide

  摘要：

  The potent cholinergic agonist (+/-)-cis-2-methyl-5-[(dimethylamino)methyl]-1,3-oxathiolane methiodide (+/-)-1] was resolved into enantiomeric forms. Their absolute configurations were established by a synthetic pathway that also allowed the synthesis of the corresponding diastereomeric (+)- and (-)-trans-2-methyl-5-[(dimethylamino)-methyl]-1,3-oxathiolane methiodide [(+)- and (-)-10]. Compound (+)-1, which is the most potent of the four isomers, showed the same absolute configuration as L-(+)-muscarine and (+)-cis-dioxolane. The four isomers were tested on guinea pig ileum and frog rectus abdominis, and their muscarinic and nicotinic potency (EPMR) and selectivity were determined. The relationships between stereoisomerism and potency are discussed.

  DOI：

  10.1021/jm00159a009