N-[(8Α,9S)-6'-甲氧基奎宁-9-基]-3,5-双(三氟甲基)苯亚磺酰胺 | 1092116-26-1

• 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
• 中文名称: N-[(8Α,9S)-6'-甲氧基奎宁-9-基]-3,5-双(三氟甲基)苯亚磺酰胺
• 英文名称: N-((1S)-(6-methoxyquinolin-4-yl)((2S,4S,5R)-5-vinylquinuclidin-2-yl)methyl)-3,5-bis(trifluoromethyl)benzenesulfonamide
• 英文别名: Song's catalyst；N-((1S)-(6-Methoxyquinolin-4-yl)((8R)-8-vinylquinuclidin-2-yl)methyl)-3,5-bis(trifluoromethyl)benzenesulfonamide；N-[(S)-[(2S,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl]-3,5-bis(trifluoromethyl)benzenesulfonamide
• CAS: 1092116-26-1
• 化学式: C₂₈H₂₇F₆N₃O₃S
• 分子量: 599.597
• InChiKey: NOTPKKPGQYSWQQ-FRSFCCSCSA-N

物化性质

• 熔点：
  155.5 °C
• 沸点：
  629.5±65.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  79.9
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-[(8Α,9S)-6'-甲氧基奎宁-9-基]-3,5-双(三氟甲基)苯亚磺酰胺 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以89%的产率得到
  参考文献：
  名称：

  奎宁为基础的串联氮杂-亨利反应环化的三官能有机催化剂：吡咯并吲哚-吡咯烷/哌啶的不对称合成。

  摘要：

  已开发出奎宁衍生的三官能磺酰胺催化剂，用于伊斯兰衍生的酮亚胺和硝基烷-甲磺酸酯的有效不对称有机催化串联aza-Henry反应-环化反应，以合成螺吡咯烷/哌啶-吲哚。传统双功能催化剂的脱甲基结合一个额外的氢键C6'-OH基团对显着的对映选择性起着关键作用。

  DOI：

  10.1021/acs.orglett.7b02150
• 作为产物：
  描述：

  在 ammonium hydroxide 、 水 作用下， 以100%的产率得到N-[(8Α,9S)-6'-甲氧基奎宁-9-基]-3,5-双(三氟甲基)苯亚磺酰胺
  参考文献：
  名称：

  An improved asymmetric total synthesis of (+)-biotin via the enantioselective desymmetrization of a meso-cyclic anhydride mediated by cinchona alkaloid-based sulfonamide

  摘要：

  The highly enantioselective total synthesis of (+)-biotin 1 via the Hoffmann-Roche lactone-thiolactone strategy has been achieved starting from cis-1,3-dibenzyl-2-imidazolidone-4,5-dicarboxylic acid 2 with an overall yield of 35%. Two contiguous stereogenic centers at C-3a and C-6a were established through a rapid cinchona alkaloid-based sulfonamide-mediated enantioselective alcoholysis of meso-cyclic anhydride 3 to afford (4S,5R)-cinnamyl hemiester 4h, the direct precursor to (3aS,6aR)-lactone 5 with high enantioselectivity. A one-pot installation of the 4-carboxybutyl side chain was accomplished by a Fukuyama coupling reaction of (3aS,6aR)-thiolactone 6 with the organozinc reagent prepared from ethyl 5-bromopentanoate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.03.041
• 作为试剂：
  描述：

  甲醇 、 3,6-endomethylene-1,2,3,6-tetrahydrophthalic anhydride 在 N-[(8Α,9S)-6'-甲氧基奎宁-9-基]-3,5-双(三氟甲基)苯亚磺酰胺 作用下， 以 乙醚 为溶剂， 反应 5.0h， 以90%的产率得到(1R,2S,3R,4S)-3-(methoxycarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid
  参考文献：
  名称：

  高活性和对映选择性的双功能有机催化剂，可用于环酐的甲醇脱对称反应：防止催化剂聚集。

  摘要：

  DOI：

  10.1002/anie.200801636

文献信息

• Enantioselective Alcoholysis of meso-Glutaric Anhydrides Catalyzed by Cinchona-Based Sulfonamide Catalysts
  作者：Sang Eun Park、Eun Hye Nam、Hyeong Bin Jang、Joong Suk Oh、Surajit Some、Yong Seop Lee、Choong Eui Song

  DOI：10.1002/adsc.201000289

  日期：2010.9.10

  The bifunctional Cinchona‐based sulfonamide catalysts showed the highest levels of enantioselectivity reported to date in the alcoholytic desymmetrization of meso‐glutaric anhydrides. Density functional theory (DFT) computational studies provide detailed insight into the observed sense of enantioselectivity. Moreover, detailed experimental studies and single crystal X‐ray analysis confirmed that these

  双功能金鸡纳为基础的磺胺催化剂表现出的对映选择性的最高水平的alcoholytic desymmetrization报告的日期观戊二酸酐。密度泛函理论（DFT）计算研究为观察到的对映选择性提供了详细的见识。此外，详细的实验研究和单晶X射线分析证实，这些双功能有机催化剂3在溶液和固态均不会形成H键结合的自聚集体。这种方法的合成效用还在合成重要的γ-氨基酸（例如（S）-普瑞巴林）中得到了证明。对映体纯（S的许多不对称合成）-迄今为止报道的普瑞巴林，我们的合成需要最少的步骤和最简单的步骤。
• [EN] CINCHONA-BASED BIFUCNTIONAL ORGANOCATALYSTS AND METHOD FOR PREPARING CHIRAL HEMIESTERS USING THE SAME<br/>[FR] CATALYSEURS ORGANIQUES BIFONCTIONNELS À BASE DE QUINQUINA ET PROCÉDÉ POUR LA FABRICATION D'HÉMIESTERS CHIRAUX LES UTILISANT
  申请人：UNIV SUNGKYUNKWAN FOUND

  公开号：WO2010008117A1

  公开（公告）日：2010-01-21

  The present invention relates to cinchona-based bifunctional organocatalysts and methods for preparing chiral hemiesters using the same. More specifically, the present invention relates to methods for preparing chiral hemiesters from prochiral or meso cyclic acid anhydrides via desymmetrization, using birunctional cinchona alkaloid catalysts comprising sulfonamide functional groups.

  本发明涉及基于金鸡纳碱的双功能有机催化剂以及利用其制备手性半酯的方法。更具体地，本发明涉及利用含有磺酰胺功能基团的双功能金鸡纳碱生催化剂，通过非对称化从原消旋或中性环酸酐制备手性半酯的方法。
• Quinine-Based Trifunctional Organocatalyst for Tandem Aza-Henry Reaction-Cyclization: Asymmetric Synthesis of Spiroxindole-Pyrrolidine/Piperidines
  作者：Saumen Hajra、Bibekananda Jana

  DOI：10.1021/acs.orglett.7b02150

  日期：2017.9.15

  A quinine-derived trifunctional sulphonamide catalyst has been developed for the effective asymmetric organocatalytic tandem aza-Henry reaction-cyclization of isatin-derived ketimines and nitroalkane-mesylates for the synthesis of spiro-pyrrolidine/piperidine-oxindoles. Demethylation of traditional bifunctional catalyst to incorporate an additional hydrogen bonding C6′–OH group plays the key role toward

  已开发出奎宁衍生的三官能磺酰胺催化剂，用于伊斯兰衍生的酮亚胺和硝基烷-甲磺酸酯的有效不对称有机催化串联aza-Henry反应-环化反应，以合成螺吡咯烷/哌啶-吲哚。传统双功能催化剂的脱甲基结合一个额外的氢键C6'-OH基团对显着的对映选择性起着关键作用。
• A Highly Reactive and Enantioselective Bifunctional Organocatalyst for the Methanolytic Desymmetrization of Cyclic Anhydrides: Prevention of Catalyst Aggregation
  作者：Sang Ho Oh、Ho Sik Rho、Ji Woong Lee、Je Eun Lee、Sung Hoon Youk、Jik Chin、Choong Eui Song

  DOI：10.1002/anie.200801636

  日期：2008.9.29
• An improved asymmetric total synthesis of (+)-biotin via the enantioselective desymmetrization of a meso-cyclic anhydride mediated by cinchona alkaloid-based sulfonamide
  作者：Fei Xiong、Xu-Xiang Chen、Fen-Er Chen

  DOI：10.1016/j.tetasy.2010.03.041

  日期：2010.4

  The highly enantioselective total synthesis of (+)-biotin 1 via the Hoffmann-Roche lactone-thiolactone strategy has been achieved starting from cis-1,3-dibenzyl-2-imidazolidone-4,5-dicarboxylic acid 2 with an overall yield of 35%. Two contiguous stereogenic centers at C-3a and C-6a were established through a rapid cinchona alkaloid-based sulfonamide-mediated enantioselective alcoholysis of meso-cyclic anhydride 3 to afford (4S,5R)-cinnamyl hemiester 4h, the direct precursor to (3aS,6aR)-lactone 5 with high enantioselectivity. A one-pot installation of the 4-carboxybutyl side chain was accomplished by a Fukuyama coupling reaction of (3aS,6aR)-thiolactone 6 with the organozinc reagent prepared from ethyl 5-bromopentanoate. (C) 2010 Elsevier Ltd. All rights reserved.