9-O-tert-butyldimethylsilyl-10,11-dihydroquinidine-11-carboxylic acid | 247096-90-8

• 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-dihydroquinidine-11-carboxylic acid
• 英文别名: 2-[(3R,4S,6R)-6-[(S)-[tert-butyl(dimethyl)silyl]oxy-(6-methoxyquinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-3-yl]acetic acid
• CAS: 247096-90-8
• 化学式: C₂₆H₃₈N₂O₄Si
• 分子量: 470.684
• InChiKey: GLCTXNPBNXEDDS-RQDMQHKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  71.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-O-tert-butyldimethylsilyl-10,11-dihydroquinidine-11-carboxylic acid 在 盐酸 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 、 2,6-二氯苯甲酰氯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 {(3R,4S,6R)-6-[(S)-(tert-Butyl-dimethyl-silanyloxy)-(6-methoxy-quinolin-4-yl)-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-acetic acid (S)-((2R,4S,5R)-5-methoxycarbonylmethyl-1-aza-bicyclo[2.2.2]oct-2-yl)-(6-methoxy-quinolin-4-yl)-methyl ester
  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-dihydro-11-hydroxyquinidine 在 jones reagent 作用下， 以 丙酮 为溶剂， 以62%的产率得到9-O-tert-butyldimethylsilyl-10,11-dihydroquinidine-11-carboxylic 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

文献信息

• Effects of Shape on Thermodynamic Cyclizations of Cinchona Alkaloids
  作者：Stuart J. Rowan、Dominic J. Reynolds、Jeremy K. M. Sanders

  DOI：10.1021/jo982496x

  日期：1999.8.1

  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.