{(1S,3R,4S,6S)-6-[(R)-(2-{(1S,3R,4S,6S)-6-[(R)-Hydroxy-(6-methoxy-quinolin-4-yl)-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-acetoxy)-(6-methoxy-quinolin-4-yl)-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-acetic acid | 182633-21-2

• 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)-(2-{(1S,3R,4S,6S)-6-[(R)-Hydroxy-(6-methoxy-quinolin-4-yl)-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-acetoxy)-(6-methoxy-quinolin-4-yl)-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-acetic acid
• CAS: 182633-21-2
• 化学式: C₄₀H₄₆N₄O₇
• 分子量: 694.828
• InChiKey: BBBKMXPEAXRIPL-HTCCUCTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  51.0
• 可旋转键数：
  11.0
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  134.55
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  {(1S,3R,4S,6S)-6-[(R)-(2-{(1S,3R,4S,6S)-6-[(R)-Hydroxy-(6-methoxy-quinolin-4-yl)-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-acetoxy)-(6-methoxy-quinolin-4-yl)-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-acetic acid 在 4-二甲氨基吡啶 、 三乙胺 、 2,6-二氯苯甲酰氯 作用下， 生成 C₈₀H₈₈N₈O₁₂ 、 C₁₂₀H₁₃₂N₁₂O₁₈
  参考文献：
  名称：

  Macrocycles Derived from Cinchona Alkaloids:  A Thermodynamic vs Kinetic Study

  摘要：

  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).

  DOI：

  10.1021/jo971813h
• 作为产物：
  描述：

  (2S,4S,8R)-2-((R)-(tert-butyldimethylsilyloxy)(6-methoxyquinolin-4-yl)methyl)-8-vinylquinuclidine 在 吗啉 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 jones reagent 、 硼烷四氢呋喃络合物 、 十二/十四烷基二甲基氧化胺 、 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 、 丙酮 为溶剂， 反应 6.5h， 生成 {(1S,3R,4S,6S)-6-[(R)-(2-{(1S,3R,4S,6S)-6-[(R)-Hydroxy-(6-methoxy-quinolin-4-yl)-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-acetoxy)-(6-methoxy-quinolin-4-yl)-methyl]-1-aza-bicyclo[2.2.2]oct-3-yl}-acetic acid
  参考文献：
  名称：

  Macrocycles Derived from Cinchona Alkaloids:  A Thermodynamic vs Kinetic Study

  摘要：

  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).

  DOI：

  10.1021/jo971813h