O-[(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethyl] N-(2,4-dimethoxyphenyl)carbamothioate | 1254701-61-5

• 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: O-[(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethyl] N-(2,4-dimethoxyphenyl)carbamothioate
• CAS: 1254701-61-5
• 化学式: C₂₈H₃₁N₃O₃S
• 分子量: 489.638
• InChiKey: BCXCCNCORRMUSS-PQJUQTFQSA-N

物化性质

• 沸点：
  628.4±65.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  87.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  辛可宁 、 2,4-二甲氧基苯基异硫氰酸酯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 12.0h， 以74%的产率得到O-[(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethyl] N-(2,4-dimethoxyphenyl)carbamothioate
  参考文献：
  名称：

  Asymmetric Bromolactonization Using Amino-thiocarbamate Catalyst

  摘要：

  A novel amino-thiocarbamate-catalyzed bromolactonization of unsaturated carboxylic acids has been developed. The scope of the reaction is evidenced by 22 examples of gamma-lactones with up to 99% yield and 93% ee. The protocol was applied in the enantioselective synthesis of the key intermediates of VLA-4 antagonists.

  DOI：

  10.1021/ja1048972
• 作为试剂：
  描述：

  4-甲基-4-戊酸 在 N-溴代丁二酰亚胺(NBS) 、 O-[(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-quinolin-4-ylmethyl] N-(2,4-dimethoxyphenyl)carbamothioate 、 4-硝基苯磺酰胺 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 126.0h， 生成 5-(bromomethyl)-5-(methyl)dihydrofuran-2(3H)-one 、 5-(bromomethyl)-5-(methyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Asymmetric Bromolactonization Using Amino-thiocarbamate Catalyst

  摘要：

  A novel amino-thiocarbamate-catalyzed bromolactonization of unsaturated carboxylic acids has been developed. The scope of the reaction is evidenced by 22 examples of gamma-lactones with up to 99% yield and 93% ee. The protocol was applied in the enantioselective synthesis of the key intermediates of VLA-4 antagonists.

  DOI：

  10.1021/ja1048972

文献信息

• Asymmetric Bromolactonization Using Amino-thiocarbamate Catalyst
  作者：Ling Zhou、Chong Kiat Tan、Xiaojian Jiang、Feng Chen、Ying-Yeung Yeung

  DOI：10.1021/ja1048972

  日期：2010.11.10

  A novel amino-thiocarbamate-catalyzed bromolactonization of unsaturated carboxylic acids has been developed. The scope of the reaction is evidenced by 22 examples of gamma-lactones with up to 99% yield and 93% ee. The protocol was applied in the enantioselective synthesis of the key intermediates of VLA-4 antagonists.