9-desoxy-9-chloroquinine | 83610-87-1

• 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: 9-desoxy-9-chloroquinine
• 英文别名: (9S)-9-chloroquinine；9-epi-Chloroquinine；9-epichloroquinine；Cinchonan, 9-chloro-6'-methoxy-, (8alpha,9S)-；4-[(S)-chloro-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]methyl]-6-methoxyquinoline
• CAS: 83610-87-1
• 化学式: C₂₀H₂₃ClN₂O
• 分子量: 342.868
• InChiKey: KQRKDUSVAAFOOA-FEBSWUBLSA-N

物化性质

• 沸点：
  482.8±40.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  25.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-desoxy-9-chloroquinine 在 silver benzoate 作用下， 生成 (1S)-6endo-ethyl-3ξ-methoxy-2ξ-(6-methoxy-[4]quinolyl)-1-aza-bicyclo[3.2.2]nonane
  参考文献：
  名称：

  Rabe, Justus Liebigs Annalen der Chemie, 1949, vol. 561, p. 154 Anm. 75

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氯化亚砜 作用下， 生成 9-desoxy-9-chloroquinine
  参考文献：
  名称：

  Pouwels; Veldstra, Recueil des Travaux Chimiques des Pays-Bas, 1955, vol. 74, p. 795,801

  摘要：

  DOI：

文献信息

• Highly tunable arylated cinchona alkaloids as bifunctional catalysts
  作者：Cormac Quigley、Zaida Rodríguez-Docampo、Stephen J. Connon

  DOI：10.1039/c1cc14684j

  日期：——

  We report the design and evaluation of a library of chiral bifunctional organocatalysts in which the distance between the catalytically active units can be systematically varied.

  我们报道了一种手性双功能有机催化剂库的设计与评估，其中催化活性单元之间的距离可以系统地变化。
• Structure and Mechanism in Cinchona Alkaloid Chemistry: Overturning a 50-Year-Old Misconception
  作者：Wilfried M. Braje、Rudolf Wartchow、H. Martin R. Hoffmann

  DOI：10.1002/(sici)1521-3773(19990903)38:17<2539::aid-anie2539>3.0.co;2-c

  日期：1999.9.3

  Long-standing errors of the supposedly established literature, including textbooks and data bases have been corrected: The structure of the hetero-cinchona bases in the crystal and in solution (see scheme) and the mechanism of their formation from quinine and quinidine have been elucidated.

  纠正了公认的长期存在的错误，包括教科书和数据库：晶体和溶液中异金鸡纳碱的结构（见方案）以及由奎宁和奎尼丁形成的机理已得到阐明。 。
• New Functional Derivatives of 9-Phenylquinine
  作者：Jacek Skarżewski、Przemysaw Boratyński

  DOI：10.1055/s-0029-1216933

  日期：2009.9

  A rapid synthesis of various 9-aryl derivatives of quinine is presented. They are obtained via coupling reactions of functionalized arylmagnesium halides and 9-chloroquinine.

  本文介绍了奎宁的各种 9-芳基衍生物的快速合成方法。它们是通过官能化芳基卤化镁和 9-氯奎宁的偶联反应获得的。
• Stereoselective C9 Carbon−Carbon Couplings of Quinine: Synthesis and Conformational Analysis of New <i>C</i>₂-Symmetric Dimers
  作者：Przemysław J. Boratyński、Ilona Turowska-Tyrk、Jacek Skarżewski

  DOI：10.1021/jo801205n

  日期：2008.9.19

  An unexpected stereoselective direct dimerization Occurred when 9-quinine halide was treated with butyllithium. The reaction of either (9S)- or (9R)-chloroquinine gave the same C-2-symmetric dimer with 9R configuration (X-ray structure). A tentative mechanism involving radical recombination is discussed. This highly congested dimer forms two atropisomers, and their reversible interconversion was studied by NMR. Another C-2-symmetric (9S)-quinine dinner connected solely by carbon-carbon bonds was obtained by the stereoselective coupling of bis(arylbromomagnesium) derivative with (9S)-chloroquinine.
• Chiral benzisoselenazolones: conformational analysis based on experimental and DFT calculated 77Se NMR
  作者：Mariola Zielińska-Błajet、Przemysław J. Boratyński、Jerzy Palus、Jacek Skarżewski

  DOI：10.1016/j.tet.2013.10.049

  日期：2013.12

  A series of new enantiomeric N-substituted benzisoselenazol-3(2H)-ones were prepared from 2-(chloroseleno)benzoyl chloride and 9-amino-deoxyquinine (both 9-native and 9-epi) as well as the other chiral primary amines. The Se-77 NMR parameters for the obtained benzisoselenazolones were measured and theoretically calculated at the DFT level of theory using B97-2 hybrid functional and ccpVTZ basis set. The DFT Se-77 chemical shifts for the lowest energy conformers were in agreement with the experimental data, while the conformers of higher energy showed markedly worse fit. Interestingly, the preferred conformation for 2-(1-arylalkyl)-benzisoselenazolones is the gauche type (Se-N-C-H approximate to +/- 180 degrees), and it is in agreement with those observed in crystals (X-ray). The calculation predicts a much higher sensitivity for the Se-77 chemical shift of the conformation than for the corresponding C-13 data. In the Se-77 NMR spectra of chiral benzisoselenazolones with added racemic or L-N-Boc-phenylglycine, chiral discrimination could not be observed mostly due to signal broadening. In the H-1 NMR spectra, the benzisoselenazole derived from epi-9-amino-deoxyquinine induced splittings of the amino acid signals, thus allowing for discrimination of the enantiomers. (C) 2013 Elsevier Ltd. All rights reserved.