(+/-)-6-(5-chloropyridin-2-yl)-7-oxo-5-(vinyloxycarbonyloxy)-5,6-dihydropyrrolo[3,4b]pyrazine | 190369-20-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡嗪类
• 英文名称: (+/-)-6-(5-chloropyridin-2-yl)-7-oxo-5-(vinyloxycarbonyloxy)-5,6-dihydropyrrolo[3,4b]pyrazine
• 英文别名: [6-(5-chloropyridin-2-yl)-5-oxo-7H-pyrrolo[3,4-b]pyrazin-7-yl] ethenyl carbonate
• CAS: 190369-20-1
• 化学式: C₁₄H₉ClN₄O₄
• 分子量: 332.703
• InChiKey: FSLYFZQIONWLKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  94.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (+/-)-6-(5-chloropyridin-2-yl)-7-oxo-5-(vinyloxycarbonyloxy)-5,6-dihydropyrrolo[3,4b]pyrazine 生成 (S)-6-(5-chloropyridin-2-yl)-7-oxo-5-(vinyloxycarbonyloxy)-5,6-dihydropyrrolo[3,4b]pyrazine
  参考文献：
  名称：

  Tetrahedron Asymmetry 1997, 8, 995-997

  摘要：

  DOI：
• 作为产物：
  描述：

  氯甲酸乙烯酯 、 6-(5-氯-2-吡啶基)-6,7-二氢-7-羟基-5H-吡咯并[3,4-b]吡嗪-5-酮 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以75%的产率得到(+/-)-6-(5-chloropyridin-2-yl)-7-oxo-5-(vinyloxycarbonyloxy)-5,6-dihydropyrrolo[3,4b]pyrazine
  参考文献：
  名称：

  Resolution of (±)-5-substituted-6-(5-chloropyridin-2-yl)-7-oxo-5,6-dihydropyrrolo[3,4b]pyrazine derivatives-precursors of (S)-(+)-Zopiclone, catalyzed by immobilized Candida antarctica B lipase in aqueous media

  摘要：

  The enzymatic resolution of different cyclopyrrolone compounds has been performed in aqueous systems using different immobilized preparations of lipase from Candida antarctica (fraction B). The relevance of the immobilizaition protocol in the results has been shown: lipase immobilized on octadecyl-Sepabeads gave the highest stability and enantioselectivity. Commercial Novozym 435 was scarcely enantioselective in the hydrolytic process. On the other hand, the structure of the cyclopyrrolone was also found to be very important to the outcome of the reaction, the best results being achieved with compounds (+/-)-l and (+/-)-2. Thus. using compound (+/-)-2. a ee(s) of < 95% can be achieved under conditions in which the enzyme preparation can be utilized in 10 recycles without any significant detriment to the enzymatic properties (activity, enantioselectivity). Moreover, this enzyme catalyzes the hydrolytic resolution of chloromethyl carbonate (+/-)-5, a useful intermediate for the synthesis of the hypnotic agent (S)-(+)-Zopiclone. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00867-4

文献信息

• Tetrahedron Asymmetry 1997, 8, 995-997
  作者：

  DOI：——

  日期：——
• Enzymatic resolution of (±)-6-(5-chloropyridin-2-yl)-6-vinyloxy-carbonyloxy-6,7-dihydro[5H]pyrrolo[3,4-b]pyrazin-5-one. Synthesis of (+)-zopiclone
  作者：Vicente Gotor、Fernando Limeres、Roberto García、Miguel Bayod、Rosario Brieva

  DOI：10.1016/s0957-4166(97)00090-6

  日期：1997.4

  The lipase from Candida antarctica (CAL) catalyzes the resolution of a precursor of zopiclone through hydrolysis and transcarbonatation processes. (C) 1997 Elsevier Science Ltd.
• DEUTERIUM-ENRICHED ESZOPICLONE
  申请人：Czarnik Anthony W.

  公开号：US20080318964A1

  公开（公告）日：2008-12-25

  The present application describes deuterium-enriched eszopiclone, pharmaceutically acceptable salt forms thereof, and methods of treating using the same.
• [EN] DEUTERIUM-ENRICHED ESZOPICLONE<br/>[FR] ESZOPICLONE ENRICHIE EN DEUTÉRIUM
  申请人：PROTIA LLC

  公开号：WO2008157564A1

  公开（公告）日：2008-12-24

  [EN] The present application describes deuterium-enriched eszopiclone, pharmaceutically acceptable salt forms thereof, and methods of treating using the same. Deuterium-enriched can be achieved by either exchanging protons with deuterium or by synthesizing the molecule with enriched starting materials. Another object of the present invention to provide the use of a novel deuterium-enriched eszopiclone or a pharmaceutically acceptable salt thereof for the manufacture of a medicament (e g, for the treatment of insomnia).
  [FR] La présente invention concerne une eszopiclone enrichie en deutérium, ses formes salines de qualité pharmaceutique, ainsi que des méthodes de traitement dans lesquelles sont utilisées cette eszopiclone enrichie en deutérium et ses formes salines. L'enrichissement en deutérium peut être obtenu soit par échange de protons avec du deutérium ou par synthèse de la molécule avec des produits de départ enrichis. Un autre objet de la présente invention concerne l'utilisation d'une nouvelle eszopiclone enrichie en deutérium ou d'un de ses sels de qualité pharmaceutique pour la fabrication d'un médicament (pour le traitement de l'insomnie, par exemple).
• Resolution of (±)-5-substituted-6-(5-chloropyridin-2-yl)-7-oxo-5,6-dihydropyrrolo[3,4b]pyrazine derivatives-precursors of (S)-(+)-Zopiclone, catalyzed by immobilized Candida antarctica B lipase in aqueous media
  作者：Jose M Palomo、Cesar Mateo、Gloria Fernández-Lorente、Laura F Solares、Monica Diaz、Vı́ctor M Sánchez、Miguel Bayod、Vicente Gotor、Jose M Guisan、Roberto Fernandez-Lafuente

  DOI：10.1016/s0957-4166(02)00867-4

  日期：2003.2

  The enzymatic resolution of different cyclopyrrolone compounds has been performed in aqueous systems using different immobilized preparations of lipase from Candida antarctica (fraction B). The relevance of the immobilizaition protocol in the results has been shown: lipase immobilized on octadecyl-Sepabeads gave the highest stability and enantioselectivity. Commercial Novozym 435 was scarcely enantioselective in the hydrolytic process. On the other hand, the structure of the cyclopyrrolone was also found to be very important to the outcome of the reaction, the best results being achieved with compounds (+/-)-l and (+/-)-2. Thus. using compound (+/-)-2. a ee(s) of < 95% can be achieved under conditions in which the enzyme preparation can be utilized in 10 recycles without any significant detriment to the enzymatic properties (activity, enantioselectivity). Moreover, this enzyme catalyzes the hydrolytic resolution of chloromethyl carbonate (+/-)-5, a useful intermediate for the synthesis of the hypnotic agent (S)-(+)-Zopiclone. (C) 2003 Elsevier Science Ltd. All rights reserved.