(Z)-Δ^3,10-isoquinidine | 60801-73-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (Z)-Δ^3,10-isoquinidine
• 英文别名: (Z)-(S)-[(2R,4S)-5-ethylidenequinuclidin-2-yl](6-methoxyquinolin-4-yl)methanol；(S)-[(2R,5Z)-5-ethylidene-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol
• CAS: 60801-73-2
• 化学式: C₂₀H₂₄N₂O₂
• 分子量: 324.423
• InChiKey: DTEXULLZKFAGHZ-KEMZMDAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  45.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  quinidine 在 Rh/Al₂O₃ 盐酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以64%的产率得到(E)-Δ^3,10-isoquinidine
  参考文献：
  名称：

  Positional isomerization of quinine and quinidine via rhodium on alumina catalysis: practical one-step synthesis of Δ3,10-isoquinine and Δ3,10-isoquinidine

  摘要：

  The synthesis of Delta(3,10)-isoquinine (5Z,5E) and Delta(3,10)-isoquinidine (6Z,6E) was achieved in one-step through positional isomerization of the terminal alkene in the parent cinchona alkaloids using catalytic amounts of 5% Rh/Al2O3 and excess hydrochloric acid in refluxing 50% aqueous EtOH. The products were obtained in good yields as a mixture of E and Z geometric isomers and fully characterized using spectroscopic methods. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01180-8

文献信息

• Effect of Microwave Irradiation on the Catalytic Activity of Palladium Supported Catalysts in the One-Step Isomerisation of Cinchona Alkaloids to Δ3,10-Isobases
  作者：Teodozja M. Lipińska、Dominika Borowska、Natalia Swędra、Katarzyna Trochim

  DOI：10.1007/s10562-017-2169-3

  日期：2017.11

  (Al2O3, C or BaSO4), reaction time and temperature. Very good results: high yields and purity of (Z/E) Δ3,10-isomers were obtained from quinine and quinidine with 10% Pd/BaSO4 as the catalyst, which is less effective for isomerisation of cinchonine and cinchonidine. Enhancing energy efficiency can be possible when the responsive support selective absorbs of microwave energy, which is translated to the

  已在绿色介质（50% 乙醇水溶液或乙二醇与 HCl）中在受控微波加热下探索了钯固体负载 (Pd/SS) 催化剂对四种天然金鸡纳生物碱侧链一步异构化的效率。通过TLC和1H NMR光谱法监测转化进程和产物纯度。最终转化率取决于载体（Al2O3、C 或 BaSO4）、反应时间和温度。非常好的结果：以 10% Pd/BaSO4 作为催化剂，从奎宁和奎尼丁中获得高产率和纯度的 (Z/E) Δ3,10-异构体，这对辛可宁和辛可尼丁的异构化效果较差。当响应支持选择性吸收微波能量时，可以提高能量效率，
• Positional isomerization of quinine and quinidine via rhodium on alumina catalysis: practical one-step synthesis of Δ3,10-isoquinine and Δ3,10-isoquinidine
  作者：David E Portlock、Dinabandhu Naskar、Laura West、William L Seibel、Titan Gu、Howard J Krauss、X.Sean Peng、Paul M Dybas、Edward G Soyke、Stephen B Ashton、Jonathan Burton

  DOI：10.1016/s0040-4039(03)01180-8

  日期：2003.7

  The synthesis of Delta(3,10)-isoquinine (5Z,5E) and Delta(3,10)-isoquinidine (6Z,6E) was achieved in one-step through positional isomerization of the terminal alkene in the parent cinchona alkaloids using catalytic amounts of 5% Rh/Al2O3 and excess hydrochloric acid in refluxing 50% aqueous EtOH. The products were obtained in good yields as a mixture of E and Z geometric isomers and fully characterized using spectroscopic methods. (C) 2003 Elsevier Science Ltd. All rights reserved.