(5-乙基-1-氮杂双环[2.2.2]辛-2-基)甲醇 | 219794-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 奎宁环
• 中文名称: (5-乙基-1-氮杂双环[2.2.2]辛-2-基)甲醇
• 中文别名: (2R,4S,5R)-5-乙基-2-奎宁环基甲醇；(2R,4S,5R)-2-羟甲基-5-乙基奎宁环
• 英文名称: dihydroquincoridine
• 英文别名: (1S,2R,4S,5R)-2-(hydroxymethyl)-5-ethyl-1-azabicyclo[2.2.2]octane；[(2R,4S,5R)-5-Ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol
• CAS: 219794-81-7
• 化学式: C₁₀H₁₉NO
• 分子量: 169.267
• InChiKey: CWZWBZXPEJJRSS-LPEHRKFASA-N

物化性质

• 沸点：
  252.6±13.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5-乙基-1-氮杂双环[2.2.2]辛-2-基)甲醇 在 palladium on activated charcoal 三(2-氯乙基)胺 、 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 反应 8.5h， 生成 1-[(2R,4S,5R)-5-乙基-1-氮杂双环[2.2.2]辛-2-基]甲胺
  参考文献：
  名称：

  New hydrogenated and didehydrogenated 1,2-diamines of quincorine and quincoridine

  摘要：

  Four new members of the family of 1,2-diamines of quincorine and quincoridine have been synthesized, being hydrogenated and didehydrogenated at the C10-C11 fragment. The alkynes, containing an additional amino group at C9, are potentially useful building blocks for cross-coupling reactions. Additional investigations concerning the chemical properties of the molecules point to a significant impact of the remote C5 substituent on the basicity of the bridgehead nitrogen. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00320-8
• 作为产物：
  描述：

  quincoridine 在 10percent Pd/C 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以98%的产率得到(5-乙基-1-氮杂双环[2.2.2]辛-2-基)甲醇
  参考文献：
  名称：

  金鸡纳生物碱衍生的配体在催化不对称转移加氢中。

  摘要：

  衍生自金鸡纳生物碱奎宁和奎尼丁的手性奎宁环配体的集合已在芳族酮的催化不对称转移氢化中得到了评估。令人高兴的是，二胺QCI-胺和QCD-胺的[IrCl（COD）] 2络合物提供了最具活性的催化剂，能够还原一系列芳族酮，并具有出色的转化率和良好的对映选择性（最高95％ee）。这些是报道的基于喹uc啶核不对称转化的配体的最佳选择性，并提倡以假对映体形式商购的这些配体将在该催化方法和其他催化方法中得到实际应用。

  DOI：

  10.1039/b304060g

文献信息

• [EN] PROCESS FOR PREPARING DIASTEREOMERICALLY ENRICHED PHOSPHORAMIDATE DERIVATIVES OF NUCLEOSIDE COMPOUNDS FOR TREATMENT OF VIRAL INFECTIONS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE DÉRIVÉS DE PHOSPHORAMIDATES ENRICHIS EN DIASTÉRÉO-ISOMÈRES DE COMPOSÉS DE NUCLÉOSIDES, DESTINÉS AU TRAITEMENT D'INFECTIONS VIRALES
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2014008236A1

  公开（公告）日：2014-01-09

  The present invention is directed to a process for preparing diastereomerically enriched nucleoside phosphoramidates having the formula I:

  本发明涉及一种制备具有化学式I的对映异构体富集的核苷磷酰胺酯的方法。
• PROCESS FOR PREPARING DIASTEREOMERICALLY ENRICHED PHOSPHORAMIDATE DERIVATIVES OF NUCLEOSIDE COMPOUNDS FOR TREATMENT OF VIRAL INFECTIONS
  申请人：BRISTOL-MYERS SQUIBB COMPANY

  公开号：US20150183818A1

  公开（公告）日：2015-07-02

  The present invention is directed to a process for preparing diastereomerically enriched nucleoside phosphoramidates having the formula I:

  本发明涉及一种制备式I的对映体富集核苷酸磷酰胺酯的方法：
• [EN] STEREOSELECTIVE MANUFACTURE OF SELECTED PURINE PHOSPHORAMIDATES<br/>[FR] PRODUCTION STÉRÉOSÉLECTIVE DE PHOSPHORAMIDATES DE PURINE SÉLECTIONNÉS
  申请人：ATEA PHARMACEUTICALS INC

  公开号：WO2022040473A1

  公开（公告）日：2022-02-24

  The present invention provides stereoselective processes of manufacture for the phosphoramidate nucleotide Compound 1 or a pharmaceutically acceptable salt thereof.

  本发明提供了制造磷酰胺酰核苷化合物1或其药学上可接受的盐的立体选择性过程。
• Synthesis of 10,11-didehydro- and 10,11-dihydro-Quincorine and of the Quincoridine analogs: functionalized and enantiopure 1-azabicyclo[2.2.2]-octanes with four stereogenic centers
  作者：Olaf Schrake、Wilfried Braje、H.M.R. Hoffmann、R. Wartchow

  DOI：10.1016/s0957-4166(98)00364-4

  日期：1998.10

  The convenient synthesis of 10,11-didehydro-QCI (2) and of 10,11-didehydro-QCD (4) as well as 10,11-dihydro-QCI (5) and 10,11-dihydro-QCD (6) is described. Conversion of the olefinic double bond of Quincorine®1 and Quincoridine®3 into the corresponding alkynes 2 and 4 involves twofold dehydrobromination, and an important application of the solid KOH/aliquat 336 system in the key step. The structure

  方便合成10,11-二氢-QCI（2）和10,11-二氢-QCD（4）以及10,11-二氢-QCI（5）和10,11-二氢-QCD（6）描述。Quincorine的烯属双键的转化率® 1和Quincoridine ® 3为相应的炔烃2和4涉及双重脱溴化氢，并将固体KOH的一个重要应用/ ALIQUAT在关键步骤336系统。X射线晶体衍射已阐明了二氢-QCI（2）的结构。新炔烃2和4 分别比QCI和QCD更具极性和更基础。
• Synthesis of Enantiopure 1-Azabicyclo[3.2.2]nonanes via Stereoselective Capture of Chiral Carbocations
  作者：Stefanie Röper、Jens Frackenpohl、Olaf Schrake、Rudolf Wartchow、H. M. R. Hoffmann

  DOI：10.1021/ol0057378

  日期：2000.6.1

  [GRAPHICS]A new class of doubly functionalized and enantiomerically pure 1-azabicyclo[3.2.2]nonanes derived from quincorine and quincoridine is described. 2,5-Disubstituted quinuclidines with a C9-mesyloxy group were easily transformed into the corresponding halides upon treatment with lithium salts. Subsequent silver salt-mediated ring expansion stereoselectively furnished the title azabicyclics. Chiral carbocations which are configurationally stable and nonplanar are postulated to account for the striking stereoselectivity of the capture of external nucleophile. 5-Ethynyl-2-iodomethylquinuclidines afford the alpha-benzoyloxy amines rather than alpha-methoxy amines, even in MeOH.