methyl 10,11-dihydroquinidine-11-carboxylate | 219596-34-6

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 金鸡纳生物碱
• 英文名称: methyl 10,11-dihydroquinidine-11-carboxylate
• 英文别名: methyl 2-[(3R,4S,6R)-6-[(S)-hydroxy-(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-yl]acetate
• CAS: 219596-34-6
• 化学式: C₂₁H₂₆N₂O₄
• 分子量: 370.448
• InChiKey: ZTDCRNJNTQFUJL-YEEBJNCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  71.89
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 10,11-dihydroquinidine-11-carboxylate 在 18-冠醚-6 、 potassium methanolate 作用下， 以 甲苯 为溶剂， 生成 (3R,7S,8R,10S,15R,19S,20R,22S)-7,19-bis(6-methoxyquinolin-4-yl)-6,18-dioxa-1,13-diazapentacyclo[18.4.0.03,22.08,13.010,15]tetracosane-5,17-dione
  参考文献：
  名称：

  Effects of Shape on Thermodynamic Cyclizations of Cinchona Alkaloids

  摘要：

  Thermodynamic cyclizations of a series of cinchona alkaloid derivatives are investigated. An extended quinine monomer 2:HO-Ce-OMe is prepared and cyclized to produce a mixture of cyclic oligomers. Combining the extended monomer 2:HO-Ce-OMe with the previously reported cinchonidine monomer 1b:HO-Cc-OMe under thermodynamic control produces a library of quinine-derived macrocycles. Two quinidine-derived methyl ester monomers 10:HO-Cd-OMe and 16:HO-Ca-OMe are also reported. Both are preorganized to form cyclic dimers; upon carrying out the thermodynamic cyclization on a mixture of both monomers only a small percentage (5%) of the hetero-dimer is obtained. Thermodynamic cyclization of the corresponding cinchonidine derived methyl ester 1b:HO-Cc-OMe with 10:HO-Cd-OMe results in the self-sorting of the two diastereoisomers.

  DOI：

  10.1021/jo982496x
• 作为产物：
  描述：

  9-O-tert-butyldimethylsilyl-10,11-dihydroquinidine-11-carboxylic acid 在 盐酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 methyl 10,11-dihydroquinidine-11-carboxylate
  参考文献：
  名称：

  Effects of Shape on Thermodynamic Cyclizations of Cinchona Alkaloids

  摘要：

  Thermodynamic cyclizations of a series of cinchona alkaloid derivatives are investigated. An extended quinine monomer 2:HO-Ce-OMe is prepared and cyclized to produce a mixture of cyclic oligomers. Combining the extended monomer 2:HO-Ce-OMe with the previously reported cinchonidine monomer 1b:HO-Cc-OMe under thermodynamic control produces a library of quinine-derived macrocycles. Two quinidine-derived methyl ester monomers 10:HO-Cd-OMe and 16:HO-Ca-OMe are also reported. Both are preorganized to form cyclic dimers; upon carrying out the thermodynamic cyclization on a mixture of both monomers only a small percentage (5%) of the hetero-dimer is obtained. Thermodynamic cyclization of the corresponding cinchonidine derived methyl ester 1b:HO-Cc-OMe with 10:HO-Cd-OMe results in the self-sorting of the two diastereoisomers.

  DOI：

  10.1021/jo982496x