9-O-tert-butyldimethylsilyl-10,11-dihydro-11-iodo-quinidine | 247096-93-1

• 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-iodo-quinidine
• 英文别名: tert-butyl-[(S)-[(2R,4S,5R)-5-(2-iodoethyl)-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methoxy]-dimethylsilane
• CAS: 247096-93-1
• 化学式: C₂₆H₃₉IN₂O₂Si
• 分子量: 566.598
• InChiKey: BSYWQCFGEIYSMY-XDESJKQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.84
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  34.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-O-tert-butyldimethylsilyl-10,11-dihydro-11-iodo-quinidine 在 18-冠醚-6 、 potassium methanolate 、 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 、 甲苯 为溶剂， 生成
  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-tosyloxy-quinidine 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以79%的产率得到9-O-tert-butyldimethylsilyl-10,11-dihydro-11-iodo-quinidine
  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