(+/-)-5-(2-chloroethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-7-oxo-5,6-dihydropyrrolo[3,4b]pyrazine | 508169-17-3

• 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: (+/-)-5-(2-chloroethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-7-oxo-5,6-dihydropyrrolo[3,4b]pyrazine
• 英文别名: (+/-)-7-(2-chloroethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one；2-chloroethyl [6-(5-chloropyridin-2-yl)-5-oxo-7H-pyrrolo[3,4-b]pyrazin-7-yl] carbonate
• CAS: 508169-17-3
• 化学式: C₁₄H₁₀Cl₂N₄O₄
• 分子量: 369.164
• InChiKey: SFQUAPARFCAVAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 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：

  (+/-)-5-(2-chloroethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-7-oxo-5,6-dihydropyrrolo[3,4b]pyrazine 在 吡啶 、 phosphate buffer 、 Candida antarctica lipase B Novozym 435 作用下， 以 水 、 甲苯 为溶剂， 反应 96.0h， 生成 (+/-)-7-(p-nitrophenyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one
  参考文献：
  名称：

  Enzymatic resolution of new carbonate intermediates for the synthesis of (S)-(+)-zopiclone

  摘要：

  The lipase from Candida antaretica B catalyzes the enantioselective hydrolysis of (+/-)-6-(5-chloropyridin-2-yl)-7-chloromethyloxycarbonyloxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one, a useful intermediate in the synthesis of (S)-(+)-zopiclone. This enzyme also catalyzes the resolution of the corresponding 2-chloroethylcarbonate derivative. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00685-7
• 作为产物：
  描述：

  7-氯甲基氧基-羰基氧基-6-(5-氯吡啶-2-基)-6,7-二氢-5H-吡咯并[3,4-b]吡嗪-5-酮 在 吡啶 、 phosphate buffer 、 Candida antarctica lipase B Chirazyme-L₂ 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 103.0h， 生成 (+/-)-5-(2-chloroethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-7-oxo-5,6-dihydropyrrolo[3,4b]pyrazine
  参考文献：
  名称：

  Enzymatic resolution of new carbonate intermediates for the synthesis of (S)-(+)-zopiclone

  摘要：

  The lipase from Candida antaretica B catalyzes the enantioselective hydrolysis of (+/-)-6-(5-chloropyridin-2-yl)-7-chloromethyloxycarbonyloxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one, a useful intermediate in the synthesis of (S)-(+)-zopiclone. This enzyme also catalyzes the resolution of the corresponding 2-chloroethylcarbonate derivative. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00685-7

文献信息

• Optically active carbonates as precursors of (+)-zopiclone
  申请人：Bayod Jasanada Miguel

  公开号：US06969767B1

  公开（公告）日：2005-11-29

  In the present invention new compounds of formula II, in enantiomerically enriched forms, are described for the first time, where R 1 is chloroalkyl. The present invention also includes several new enzymatic processes for the resolution of the enantiomers of the aforementioned carbonates of formula II from the corresponding racemic mixture. The transformation of these carbonates into zopiclone enantiomerically enriched, constitutes an additional aspect of the invention.

  在本发明中，首次描述了式II的新化合物，其为对映富集形式，其中R1为氯代烷基。本发明还包括几种新的酶法过程，用于从相应的外消旋混合物中分离出式II的上述碳酸酯的对映体。将这些碳酸酯转化为对映富集的左西普克隆，构成了本发明的另一个方面。
• 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.
• Methods and compositions for the treatment of neurodegenerative disorders
  申请人：Jin Xiaowei

  公开号：US20080044390A1

  公开（公告）日：2008-02-21

  The present invention features compositions, kits, and methods for treating, preventing, and ameliorating neurodegenerative disorders, e.g., Huntington's disease.
• US6969767B1
  申请人：——

  公开号：US6969767B1

  公开（公告）日：2005-11-29
• Enzymatic resolution of new carbonate intermediates for the synthesis of (S)-(+)-zopiclone
  作者：Laura F. Solares、Mónica Dı́az、Rosario Brieva、Vı́ctor M. Sánchez、Miguel Bayod、Vicente Gotor

  DOI：10.1016/s0957-4166(02)00685-7

  日期：2002.11

  The lipase from Candida antaretica B catalyzes the enantioselective hydrolysis of (+/-)-6-(5-chloropyridin-2-yl)-7-chloromethyloxycarbonyloxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one, a useful intermediate in the synthesis of (S)-(+)-zopiclone. This enzyme also catalyzes the resolution of the corresponding 2-chloroethylcarbonate derivative. (C) 2002 Elsevier Science Ltd. All rights reserved.