9S-chloro-9-deoxy-10,11-dihydroquinine | 1007362-85-7

• 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: 9S-chloro-9-deoxy-10,11-dihydroquinine
• 英文别名: (9S)-9-chloro-10,11-dihydroquinine；(8I+/-,9S)-9-Chloro-10,11-dihydro-6a(2)-methoxycinchonan；4-[(S)-chloro-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methyl]-6-methoxyquinoline
• CAS: 1007362-85-7
• 化学式: C₂₀H₂₅ClN₂O
• 分子量: 344.884
• InChiKey: PKVFHIWLSUJSDY-FEBSWUBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  9S-chloro-9-deoxy-10,11-dihydroquinine 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以36%的产率得到bis((8S,9R)-6'-methoxy-10,11-dihydrocinchonan-9-yl)
  参考文献：
  名称：

  Stereoselective C9 Carbon−Carbon Couplings of Quinine: Synthesis and Conformational Analysis of New C₂-Symmetric Dimers

  摘要：

  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.

  DOI：

  10.1021/jo801205n
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氯仿 、 五氯化磷 作用下， 生成 9S-chloro-9-deoxy-10,11-dihydroquinine
  参考文献：
  名称：

  Heidelberger; Jacobs, Journal of the American Chemical Society, 1920, vol. 42, p. 1497

  摘要：

  DOI：

文献信息

• Tricyclic Quaternary Ammonium Salts Derived from <i>Cinchona</i> Alkaloids
  作者：Przemysław J. Boratyński、Rafał Kowalczyk、Anna Kobylańska、Julia Bąkowicz

  DOI：10.1021/acs.joc.6b02348

  日期：2016.12.16

  bridgehead nitrogen atoms are rare but an interesting class of compounds. Chiral quinuclidine derivative salts with fused five and six-membered rings (X-ray) were obtained via modification of Cinchona alkaloids. The ease of ring formation was dependent on its size, while even mild activation sufficed to close the five membered ring. On the other hand the systems with fused benzene and a six-membered ring

  具有四级桥头氮原子的三环系统很少见，但是一类有趣的化合物。通过金鸡纳生物碱的修饰获得具有稠合的五元环和六元环的手性喹核苷衍生物盐（X射线）。形成环的难易程度取决于其大小，而即使轻度激活也足以封闭五元环。另一方面，具有稠合苯和六元环的体系形成阻转异构体，被阻隔ca隔开。15 kcal / mol，其相互转化通过DFT和NMR研究。
• Giemsa; Halberkann, Chemische Berichte, 1921, vol. 54, p. 1186
  作者：Giemsa、Halberkann

  DOI：——

  日期：——
• Stereoselective C9 Arylation and Vinylation of <i>Cinchona</i> Alkaloids
  作者：Przemysław J. Boratyński、Ilona Turowska-Tyrk、Jacek Skarżewski

  DOI：10.1021/ol7026625

  日期：2008.2.1

  A simple and efficient method for the highly stereoselective C-9 arylation and vinylation of Cinchona alkaloids was developed. Both 9s- and 9R-chloroquinine with PhMgBr yielded 9S-phenylquinine (X-ray structure). The reactions with various aryl and vinyl Grignard reagents resulted in the series of 9S-aryl and vinyl alkaloid derivatives. The stereochemical outcome was rationalized by coordination of the magnesium atom to the quinuclidine nitrogen, thus directing the nucleophilic attack at the C-9 stereogenic center.