{(1S,3R,4S,6S)-6-[(R)-(tert-Butyl-dimethyl-silanyloxy)-quinolin-4-yl-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-acetic acid methyl ester | 183994-29-8

• 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: {(1S,3R,4S,6S)-6-[(R)-(tert-Butyl-dimethyl-silanyloxy)-quinolin-4-yl-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-acetic acid methyl ester
• CAS: 183994-29-8
• 化学式: C₂₆H₃₈N₂O₃Si
• 分子量: 454.685
• InChiKey: TZSDPOLAXABTNB-HUFIRRDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.57
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  51.66
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  {(1S,3R,4S,6S)-6-[(R)-(tert-Butyl-dimethyl-silanyloxy)-quinolin-4-yl-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-acetic acid methyl ester 在 KOMe*18-crown-6 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (3R,7R,8S,10S,15R,19R,20S,22S,27R,31R,32S,34S)-7,19,31-tri(quinolin-4-yl)-6,18,30-trioxa-1,13,25-triazaheptacyclo[30.4.0.03,34.08,13.010,15.020,25.022,27]hexatriacontane-5,17,29-trione
  参考文献：
  名称：

  Rowan, Stuart J.; Brady, Paul A.; Sanders, Jeremy K. M., Angewandte Chemie, 1996, vol. 108, # 18, p. 2283 - 2285

  摘要：

  DOI：
• 作为产物：
  描述：

  4-[(R)-(tert-Butyl-dimethyl-silanyloxy)-((1S,2S,4S,5R)-5-vinyl-1-aza-bicyclo[2.2.2]oct-2-yl)-methyl]-quinoline 在 盐酸 、 jones' reagent 、 硼烷四氢呋喃络合物 、 十二/十四烷基二甲基氧化胺 作用下， 以 丙酮 为溶剂， 反应 2.0h， 生成 {(1S,3R,4S,6S)-6-[(R)-(tert-Butyl-dimethyl-silanyloxy)-quinolin-4-yl-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-acetic acid methyl ester
  参考文献：
  名称：

  Rowan, Stuart J.; Brady, Paul A.; Sanders, Jeremy K. M., Angewandte Chemie, 1996, vol. 108, # 18, p. 2283 - 2285

  摘要：

  DOI：

文献信息

• Macrocycles Derived from Cinchona Alkaloids:  A Thermodynamic vs Kinetic Study
  作者：Stuart J. Rowan、Jeremy K. M. Sanders

  DOI：10.1021/jo971813h

  日期：1998.3.1

  Cyclization of the quiuine-derived monomer (2a): HO-Cq-OMe, under thermodynamic control, gives mainly cyclic trimer Cq(3) (7a), whereas kinetic cyclization of the similar monomer HO-Cq-OH (8) gives a mixture of cyclic products. This difference in product distribution is attributed to predisposition of the monomer unit, which means the building block adopts a more stable conformation in cyclic trimer than it can in cyclic tetramer. The reversibility of the thermodynamic reaction was demonstrated using electrospray mass spectrometry to monitor the catalyzed mixing of the two cyclic trimers Cq(3) (7a) and Cc(3) (7b), which results in the statistically expected 1:3:3:1 ratio of all possible cyclic trimers Cc(3):Cc(2)Cq:CeCq(2):Cq(3).