9-O-tert-butyldimethylsilyl-10,11-dihydro-11-tosyl-quinine | 194983-29-4

• 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: 9-O-tert-butyldimethylsilyl-10,11-dihydro-11-tosyl-quinine
• 英文别名: Cinchonan-11-ol, 9-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-10,11-dihydro-6a(2)-methoxy-, 4-methylbenzenesulfonate (ester), (8I+/-,9R)-；2-[(3R,4S,6S)-6-[(R)-[tert-butyl(dimethyl)silyl]oxy-(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-yl]ethyl 4-methylbenzenesulfonate
• CAS: 194983-29-4
• 化学式: C₃₃H₄₆N₂O₅SSi
• 分子量: 610.89
• InChiKey: FJUBHXFDXHJZNP-PJKYEMGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.12
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  77.96
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  9-O-tert-butyldimethylsilyl-10,11-dihydro-11-tosyl-quinine 在 lithium hydroxide 、 18-冠醚-6 、 potassium carbonate 、 sodium iodide 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 27.0h， 生成 4-(2-{(3R,4S,6S)-6-[(R)-(tert-Butyl-dimethyl-silanyloxy)-(6-methoxy-quinolin-4-yl)-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-ethoxy)-benzoic acid
  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：

  对甲苯磺酰氯 、 2-{(1S,3R,4S,6S)-6-[(R)-(tert-Butyl-dimethyl-silanyloxy)-(6-methoxy-quinolin-4-yl)-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-ethanol 在 三乙胺 作用下， 反应 4.0h， 以77%的产率得到9-O-tert-butyldimethylsilyl-10,11-dihydro-11-tosyl-quinine
  参考文献：
  名称：

  Building thermodynamic combinatorial libraries of quinine macrocycles

  摘要：

  通过热力学控制，预先设定的金鸡纳啶结构单元与更灵活的扩展奎宁单体发生酯交换反应，产生了 11 种大环受体的组合混合物，并通过电喷雾质谱法对其进行了分析；生物碱-胆酸盐混合物的类似结果表明了这种方法的通用性。

  DOI：

  10.1039/a703291i