2,2-dimethyl spiro (1,3-dioxolane-4,3') quinuclidine | 60211-59-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: 2,2-dimethyl spiro (1,3-dioxolane-4,3') quinuclidine
• 英文别名: (+/-)-2,2-Dimethyl-spiro<(1.3)dioxolane-4,3'-quinuclidine>；(+/-)-2,2-Dimethyl-spiro[(1.3)dioxolane-4,3'-quinuclidine]；2',2'-Dimethylspiro[4-azabicyclo[2.2.2]octane-2,4'-[1,3]dioxolane]；2,2-dimethylspiro[1,3-dioxolane-4,3'-1-azabicyclo[2.2.2]octane]
• CAS: 60211-59-8
• 化学式: C₁₁H₁₉NO₂
• 分子量: 197.277
• InChiKey: SKIHOOFFVUKSNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  4.0
• 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

• 作为产物：
  描述：

  3-羟基-1-氮杂双环[2.2.2]辛烷-3-甲醇 、 2,2-二甲氧基丙烷 在 硫酸 作用下， 以 丙酮 为溶剂， 以36%的产率得到2,2-dimethyl spiro (1,3-dioxolane-4,3') quinuclidine
  参考文献：
  名称：

  Analogs of the muscarinic agent 2'-methylspiro[1-azabicyclo[2.2.2]octane-3,4'-[1,3]dioxolane]: synthesis and pharmacology

  摘要：

  A number of tetrahydrofuran analogues of 2'-methylspiro[1-azabicyclo[2.2.2]octane-3,4'-[1,3]dioxolane] (1) have been prepared with the aim to obtain information about the relative importance of each of the oxygens in 1 for efficacy and for selectivity. In addition, the dimethyl and desmethyl analogues of 1 were prepared. The new compounds were compared to cis- and trans-1 with regard to their ability to displace (-)-[H-3]-3-quinuclidinyl benzilate ((-)-[H-3] QNB) from muscarinic receptors in cerebral cortex, heart, parotid gland, and urinary bladder from guinea pigs. Functioinal studies were made on isolated guinea pig bladder and ileum. The new compounds exhibited both lower affinity and efficacy than cis-1. A conformational study was performed, and the effects of steric and electronic factors on the biological activity of the compounds are discussed.

  DOI：

  10.1021/jm00087a007

文献信息

• US4104397A
  申请人：——

  公开号：US4104397A

  公开（公告）日：1978-08-01
• Analogs of the muscarinic agent 2'-methylspiro[1-azabicyclo[2.2.2]octane-3,4'-[1,3]dioxolane]: synthesis and pharmacology
  作者：Gunnar Nordvall、Staffan Sundquist、Gunilla Glas、Adolf Gogoll、Lisbeth Nilvebrant、Uli Hacksell

  DOI：10.1021/jm00087a007

  日期：1992.5

  A number of tetrahydrofuran analogues of 2'-methylspiro[1-azabicyclo[2.2.2]octane-3,4'-[1,3]dioxolane] (1) have been prepared with the aim to obtain information about the relative importance of each of the oxygens in 1 for efficacy and for selectivity. In addition, the dimethyl and desmethyl analogues of 1 were prepared. The new compounds were compared to cis- and trans-1 with regard to their ability to displace (-)-[H-3]-3-quinuclidinyl benzilate ((-)-[H-3] QNB) from muscarinic receptors in cerebral cortex, heart, parotid gland, and urinary bladder from guinea pigs. Functioinal studies were made on isolated guinea pig bladder and ileum. The new compounds exhibited both lower affinity and efficacy than cis-1. A conformational study was performed, and the effects of steric and electronic factors on the biological activity of the compounds are discussed.