(2R,5R)-cis-2-methyl-5-<(dimethylamino)methyl>-1,3-oxathiolane | 103066-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧硫杂环戊烷
• 英文名称: (2R,5R)-cis-2-methyl-5-<(dimethylamino)methyl>-1,3-oxathiolane
• 英文别名: N,N-dimethyl-1-[(2R,5R)-2-methyl-1,3-oxathiolan-5-yl]methanamine
• CAS: 103066-62-2
• 化学式: C₇H₁₅NOS
• 分子量: 161.268
• InChiKey: KYQBXVDMPLOGBC-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  37.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,5R)-cis-2-methyl-5-<(dimethylamino)methyl>-1,3-oxathiolane 在 双氧水 、 溶剂黄146 作用下， 反应 24.5h， 生成 2c-methyl-5-dimethylaminomethyl-1,3-oxathiolane sulfone
  参考文献：
  名称：

  （-）-和（+）-c-2-甲基-r-5-[（二甲基氨基）甲基] -1,3-氧杂硫杂环戊酸酯t-3-氧化物甲硫醚和相关砜的拆分，绝对构型和胆碱能对映选择性。

  摘要：

  作为先前对带有1,3-氧杂硫杂环戊烷核的手性胆碱能激动剂的研究的继续，c-2-甲基-r-5-[（二甲基氨基）甲基] -1,3-氧杂硫杂环戊烷t-3-氧化物甲硫醇的对映体（（+）-和（-）-1）和顺式-2-甲基-5-[（二甲基氨基）甲基] -1,3-氧杂硫杂环戊烷3,3-二氧化物（（+）-和（-）-2获得），并通过合成建立它们的绝对构型。在豚鼠回肠和青蛙直肌腹部模型上对四种异构体的胆碱能效价进行了体外评估，结果表明，具有与L-（+）-毒蕈碱相同的绝对构型的（-）-1是选择性的和有效的毒蕈碱剂。（+）-1对映异构体在毒蕈碱性豚鼠回肠上的效价比（-）-1低数百倍，而在同一组织上，相应的砜衍生物（（+）-和（-）-2）没有对映选择性。

  DOI：

  10.1021/jm00393a042
• 作为产物：
  描述：

  methyl (2S,5R)-trans-2-methyl-1,3-oxathiolane-5-carboxylate 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 28.0h， 生成 (2R,5R)-cis-2-methyl-5-<(dimethylamino)methyl>-1,3-oxathiolane
  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

文献信息

• PIGINI M.; GIANNELLA M.; GUALTIERI F., SYNTH. COMMUN., 1980, 10, NO 10, 725-732
  作者：PIGINI M.、 GIANNELLA M.、 GUALTIERI F.

  DOI：——

  日期：——
• TEODORI E.; GUALTIERI F.; ANGELI P.; BRASILI L.; GIANNELLA M.; PIGINI M., J. MED. CHEM., 29,(1986) N 9, 1610-1615
  作者：TEODORI E.、 GUALTIERI F.、 ANGELI P.、 BRASILI L.、 GIANNELLA M.、 PIGINI M.

  DOI：——

  日期：——
• TEODORI, E.;GUALTIERI, F.;ANGELI, P.;BRASILI, L.;GIANNELLA, M., J. MED. CHEM., 30,(1987) N 10, 1934-1938
  作者：TEODORI, E.、GUALTIERI, F.、ANGELI, P.、BRASILI, L.、GIANNELLA, M.

  DOI：——

  日期：——
• 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
  作者：Elisabetta Teodori、Fulvio Gualtieri、Piero Angeli、Livio Brasili、Mario Giannella、Maria Pigini

  DOI：10.1021/jm00159a009

  日期：1986.9

  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.
• Molecular requirements of the recognition site of the cholinergic receptor. 24. Resolution, absolute configuration, and cholinergic enantioselectivity of (-)- and (+)-c-2-methyl-r-5-[(dimethylamino)methyl]-1,3-oxathiolane t-3-oxide methiodide and related sulfones
  作者：E. Teodori、F. Gualtieri、P. Angeli、L. Brasili、M. Giannella

  DOI：10.1021/jm00393a042

  日期：1987.10

  the four isomers was evaluated in vitro on guinea pig ileum and frog rectus abdominis models, and the results show that (-)-1, which has the same absolute configuration as L-(+)-muscarine, is a selective and potent muscarinic agent. The (+)-1 enantiomer is some hundred times less potent than (-)-1 on the muscarinic guinea pig ileum while, on the same tissue, the corresponding sulfone derivatives ((+)-

  作为先前对带有1,3-氧杂硫杂环戊烷核的手性胆碱能激动剂的研究的继续，c-2-甲基-r-5-[（二甲基氨基）甲基] -1,3-氧杂硫杂环戊烷t-3-氧化物甲硫醇的对映体（（+）-和（-）-1）和顺式-2-甲基-5-[（二甲基氨基）甲基] -1,3-氧杂硫杂环戊烷3,3-二氧化物（（+）-和（-）-2获得），并通过合成建立它们的绝对构型。在豚鼠回肠和青蛙直肌腹部模型上对四种异构体的胆碱能效价进行了体外评估，结果表明，具有与L-（+）-毒蕈碱相同的绝对构型的（-）-1是选择性的和有效的毒蕈碱剂。（+）-1对映异构体在毒蕈碱性豚鼠回肠上的效价比（-）-1低数百倍，而在同一组织上，相应的砜衍生物（（+）-和（-）-2）没有对映选择性。

表征谱图