(8S,9R)-9-azido-(9-deoxy)quinine | 1071476-92-0

• 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: (8S,9R)-9-azido-(9-deoxy)quinine
• 英文别名: 9-azido(9-deoxy)quinine；(8I+/-,9R)-9-Azido-6a(2)-methoxycinchonan；4-[(R)-azido-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]methyl]-6-methoxyquinoline
• CAS: 1071476-92-0
• 化学式: C₂₀H₂₃N₅O
• 分子量: 349.436
• InChiKey: OUXQZBYQVPSMLR-WZBLMQSHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  39.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (8S,9R)-9-azido-(9-deoxy)quinine 在 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  An easy route to exotic 9-epimers of 9-amino-(9-deoxy) cinchona alkaloids with (8S, 9R) and (8R, 9S)-configurations through two inversions of configuration

  摘要：

  Four exotic chiral organocatalysts, 9-amino-(9-deoxy) cinchona alkaloids with (8S, 9R) and (8R, 9S)-configurations, were conveniently synthesized for the first time in 27-72% total yields through two conversions of configuration at the 9-stereogenic centers of commercially available cinchona alkaloids. (C) 2013 Xue-Bing Ma and Ming Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.12.008
• 作为产物：
  描述：

  quinine 4-nitrobenzoic acid ester 在 偶氮二甲酸二异丙酯 、 叠氮磷酸二苯酯 、 三苯基膦 、 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 14.0h， 生成 (8S,9R)-9-azido-(9-deoxy)quinine
  参考文献：
  名称：

  An easy route to exotic 9-epimers of 9-amino-(9-deoxy) cinchona alkaloids with (8S, 9R) and (8R, 9S)-configurations through two inversions of configuration

  摘要：

  Four exotic chiral organocatalysts, 9-amino-(9-deoxy) cinchona alkaloids with (8S, 9R) and (8R, 9S)-configurations, were conveniently synthesized for the first time in 27-72% total yields through two conversions of configuration at the 9-stereogenic centers of commercially available cinchona alkaloids. (C) 2013 Xue-Bing Ma and Ming Li. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2013.12.008

文献信息

• Synthesis of Novel C 2-Symmetric Sulfur-Based Catalysts: Asymmetric Formation of Halo- and Seleno-Functionalized Normal- and Medium-Sized Rings
  作者：Sadhan Jana、Ajay Verma、Vandana Rathore、Sangit Kumar

  DOI：10.1055/s-0037-1610715

  日期：2019.9

  The synthesis of novel, highly functionalized, C 2-symmetric sulfur-based catalysts is developed and their catalytic applications are explored in asymmetric bromo-, iodo- and seleno-functionalizations of alkenoic acids. This protocol provides the corresponding normal- and medium-sized bromo, iodo and selenolactones in up to 98% yield and 83% stereoselectivity.

  开发了新型、高度官能化的 C 2 对称硫基催化剂的合成，并探索了它们在烯酸的不对称溴、碘和硒官能化中的催化应用。该方案以高达 98% 的产率和 83% 的立体选择性提供相应的正常和中等大小的溴、碘和硒内酯。
• An eccentric rod-like linear connection of two heterocycles: synthesis of pyridine <i>trans</i>-tetrafluoro-λ⁶-sulfanyl triazoles
  作者：Prajwalita Das、Kiyoteru Niina、Tomoya Hiromura、Etsuko Tokunaga、Norimichi Saito、Norio Shibata

  DOI：10.1039/c8sc01216d

  日期：——

  The trans-tetrafluoro-λ6-sulfane (SF4) group has been utilized as a unique three-dimensional building block for the linear connection of two independent N-heterocycles, pyridines and triazoles. The linearly connected heterocyclic compounds were synthesized by thermal Huisgen 1,3-dipolar cycloaddition between previously unknown pyridine SF4-alkynes and readily available azides, providing a series of

  的反式-四氟λ 6 -sulfane（SF 4）基团已被用作一种独特的三维构造块的两个独立的N杂环，吡啶和三唑的线性连接。线性连接的杂环化合物是通过在先前未知的吡啶SF 4-炔烃和易于获得的叠氮化物之间进行热Huisgen 1,3-偶极环加成反应合成的，从而提供了一系列棒状SF 4连接的N-杂环，收率良好。目标产品的X射线晶体学分析显示SF 4的反式几何结构基团，其线性连接两个独立的N杂环。这项研究将打开SF 4连接的杂环化合物的化学领域。
• Kinetic resolution of phosphoric diester by Cinchona alkaloid derivatives provided with a guanidinium unit
  作者：Riccardo Salvio、Mauro Moliterno、Dario Caramelli、Luca Pisciottani、Achille Antenucci、Melania D'Amico、Marco Bella

  DOI：10.1039/c5cy01208b

  日期：——

  Cinchona alkaloid derivatives featuring a guanidinium group in diverse positions efficiently catalyze the cleavage of the RNA model compound 2-hydroxypropyl p-nitrophenyl phosphate (HPNP). Their high catalytic efficiency as phosphodiesterases and the potentiometric and kinetic investigations indicate the existence of a high degree of cooperation between the guanidinium group and the quinuclidine moiety

  在不同位置具有胍基的金鸡纳生物碱衍生物可有效催化RNA模型化合物2-羟丙基对硝基苯基磷酸酯（HPNP）的裂解。它们作为磷酸二酯酶的高催化效率以及电位和动力学研究表明，在一般的酸/一般碱机制的作用下，胍鎓基团和喹核苷部分之间存在高度的协同作用。研究了这些化合物的性能，并在HPNP的动力学拆分中进行了比较。这些数据还与酯交换反应过渡态的DFT计算结果进行了比较，该结果部分预测和合理化了实验数据。
• <i>Click</i>-Dimerized <i>Cinchona</i> Alkaloids
  作者：Przemysław J. Boratyński、Rafał Kowalczyk

  DOI：10.1021/acs.joc.6b01403

  日期：2016.9.2

  A series of Cinchona alkaloid-derived dimers were obtained in high yields in copper-catalyzed 1,3-dipolar “click” cycloaddition using bis(TMS)butadiyne and other bivalent alkynes. The products with bitriazole linkers were effective ligands for asymmetric copper-catalyzed Michael addition. It was shown that the presence of such linker was responsible for effective chirality transfer.

  使用bis（TMS）丁二炔和其他二价炔烃，在铜催化的1,3-偶极“点击”环加成中以高收率获得了一系列Cinchona生物碱衍生的二聚体。具有三氮唑连接基的产物是不对称铜催化的迈克尔加成反应的有效配体。结果表明，这种连接基的存在是有效手性转移的原因。
• Accessing Chiral Pyrrolodiketopiperazines under Organocatalytic Conditions
  作者：Eider Duñabeitia、Aitor Landa、Rosa López、Claudio Palomo

  DOI：10.1021/acs.orglett.2c03924

  日期：2023.1.13

  The production of chiral pyrrolodiketopiperazines under organocatalytic conditions demonstrates the capacity of bicyclic acylpyrrol lactims to perform as pronucleophiles in direct carbon–carbon bond forming reactions. The good performance of ureidoaminal-derived Brønsted bases in the Michael addition to nitroolefins affords these heterocyclic scaffolds with high skeleton diversity.

  在有机催化条件下生产手性吡咯二酮哌嗪证明了双环酰基吡咯内酰亚胺在直接碳-碳键形成反应中作为亲核试剂的能力。脲醛衍生的布朗斯台德碱在硝基烯烃的迈克尔加成中的良好性能为这些杂环支架提供了高骨架多样性。