N-benzylquininium bromide

• 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: N-benzylquininium bromide
• 英文别名: (R)-[(2S,4S,5R)-1-benzyl-5-ethenyl-1-azoniabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;bromide
• 化学式: Br*C₂₇H₃₁N₂O₂
• 分子量: 495.459
• InChiKey: OYFFKUHRLDMNOP-UNGVVQABSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.89
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzylquininium bromide 、 奥美拉唑 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 (R)-omeprazole N-benzylquinine salt 、 (S)-omeprazole N-benzylquinine salt
  参考文献：
  名称：

  Process for the preparation of optically pure omeprazole via salt formation with a chiral amine

  摘要：

  本发明涉及一种制备基本光学纯的奥美拉唑或其药用盐或溶剂的方法。本发明还涉及一种制备含基本光学纯的奥美拉唑或其药用盐或溶剂的制药组合物的方法，以及用于制备光学纯奥美拉唑的中间体。

  公开号：

  EP2048144A1
• 作为产物：
  描述：

  溴甲苯 、 奎宁 以 甲醇 为溶剂， 以85%的产率得到N-benzylquininium bromide
  参考文献：
  名称：

  Highly selective recognition of carbenicillin via concerted interactions in 100% aqueous solution

  摘要：

  我们合成了一种基于含有两个季铵基和一条长疏水链的奎宁的荧光探针（QA），该探针通过协同作用对 100% 水溶液中的羧苄青霉素（一种典型的 beta-内酰胺类抗生素）具有高度选择性识别能力。

  DOI：

  10.1039/b923318k

文献信息

• Preparation and Chiroptical Studies of Dendritic Alkaloid Derivatives
  作者：Uwe Hahn、Astrid Kaufmann、Martin Nieger、Ondřej Julínek、Marie Urbanova、Fritz Vögtle

  DOI：10.1002/ejoc.200500819

  日期：2006.3

  A series of dendritic substituted alkaloids, deriving from quinine or atropine and Frechet-type dendrons up to generation three, have been prepared. Enantioseparation of the dendronized atropine ammonium salts was achieved by HPLC on chiral stationary phases. Investigation of the chiroptical properties of the series of dendrimers by circular dichroism spectroscopy revealed an influence of the chiral

  一系列树突取代的生物碱，从奎宁或阿托品和 Frechet 型树突衍生到第三代，已被制备出来。树枝状阿托品铵盐的对映分离是通过 HPLC 在手性固定相上实现的。通过圆二色光谱对一系列树枝状聚合物的手性光学特性的研究揭示了手性核对树枝状部分的影响，与棉花带的强度有关。发现手性取决于其手性元素和附着在手性核上的正式非手性树突分支的产生（“树突效应”）。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
• Enantioselective α-Arylation of Cyclic Ketones Catalyzed by a Combination of an Unmodified Cinchona Alkaloid and a Palladium Complex
  作者：Christian Richter、Kalluri V. S. Ranganath、Frank Glorius

  DOI：10.1002/adsc.201100669

  日期：2012.2

  A palladium/Cinchona alkaloid-catalyzed α-arylation between cyclic ketones and aryl halides under phosphine-free conditions is presented. The use of a simple, unmodified Cinchona alkaloid results in high levels of activity and selectivity with up to 93% ee. These enantioinduction levels are comparable or even higher than the ones reported using palladium/BINAP complexes. To the best of our knowledge

  提出了在无膦条件下，环酮与芳基卤化物之间钯/金鸡纳生物碱催化的α-芳基化反应。使用简单的未经修饰的金鸡纳生物碱可导致高水平的活性和选择性，ee最高可达93％。这些对映体诱导水平与使用钯/ BINAP复合物所报道的对映体诱导水平相当或什至更高。据我们所知，这代表未修饰的金鸡纳生物碱在不对称过渡金属络合物催化的交叉偶联反应中首次用作配体/催化剂。
• Highly selective recognition of carbenicillin via concerted interactions in 100% aqueous solution
  作者：Lintao Zeng、Weimin Liu、Xiaoqing Zhuang、Jiasheng Wu、Pengfei Wang、Wenjun Zhang

  DOI：10.1039/b923318k

  日期：——

  A fluorescent probe (QA) based on quinine bearing two quaternary ammonium groups and a long hydrophobic chain was synthesized, and it showed highly selective recognition of carbenicillin (a typical beta-lactam antibiotic) in 100% aqueous solution via concerted interactions.

  我们合成了一种基于含有两个季铵基和一条长疏水链的奎宁的荧光探针（QA），该探针通过协同作用对 100% 水溶液中的羧苄青霉素（一种典型的 beta-内酰胺类抗生素）具有高度选择性识别能力。
• Organocatalytic Activity of Cinchona Alkaloids: Which Nitrogen Is More Nucleophilic?
  作者：Mahiuddin Baidya、Markus Horn、Hendrik Zipse、Herbert Mayr

  DOI：10.1021/jo901670w

  日期：2009.9.18

  The cinchona alkaloids 1a-d react selectively at the quinuclidine ring with benzyl bromide it and at the quinoline ring with benzhydrylium ions (diarylcarbenium ions). The kinetics of these reactions have been determined photometrically or conductimetrically and are compared with analogous reactions of quinuclidine and quinoline derivatives. Quantum chemical calculations [MP2/6-31 + G(2d p)// B3LYP/6-31G(d)] show that the products obtained by attack at the quinuclidine ring (N-sp3) of quinine are thermodynamically more stable when small alkylating agents (primary alkyl) are used, while the products arising from attack at the quinoline ring (N-sp2) are more stable for bulkier electrophiles (Ar2CH). In some cases, rate and equilibrium constants for their reactions with berizhydrylium ions could be determined. These data gave access to the Marcus intrinsic barriers, which are approximately 20 U mol(-1) lower for attack at the N-sp3-center than at the N-sp2-center.
• Phase-Transfer Catalysed Enantioselective Epoxidation of Estra-Δ5(10),9(11)-diene Using Chiral Ammonium Salts Derived from Cinchona Alkaloids
  作者：Ya-Xi Yang、Zheng Li、Guo-Rong Chen、Yuan-Chao Li

  DOI：10.2174/157017810790796237

  日期：2010.3.1

  A modified phase-transfer catalysed enantioselective epoxidation of estra-Delta(5(10),9(11))-diene, an important intermediate of anti-early pregnancy drug mifepristone 1, have been determined and investigated. Eight chiral ammonium salts (PTC A-H), used as phase-transfer catalysts, have been synthesized from cinchona alkaloids. Among them, PTC G and PTC H have exhibited satisfying catalytic activity to improve the ratio of alpha/beta epoxide up to 7:1.