ethyl N-(benzyloxycarbonyl)-3-aza-6-oxobicyclo[3.3.0]octane-2-carboxylate | 783326-26-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl N-(benzyloxycarbonyl)-3-aza-6-oxobicyclo[3.3.0]octane-2-carboxylate
• 英文别名: (3AR,6aS)-2-benzyl 1-ethyl 4-oxohexahydrocyclopenta[c]pyrrole-1,2(1H)-dicarboxylate；2-O-benzyl 3-O-ethyl 6-oxo-1,3,3a,4,5,6a-hexahydrocyclopenta[c]pyrrole-2,3-dicarboxylate
• CAS: 783326-26-1
• 化学式: C₁₈H₂₁NO₅
• 分子量: 331.368
• InChiKey: VFGHIBHHMQQACC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl N-(benzyloxycarbonyl)-3-aza-6-oxobicyclo[3.3.0]octane-2-carboxylate 在 [双(2-甲氧基乙基)胺]三氟化硫 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 72.0h， 以66%的产率得到ethyl N-(benzyloxycarbonyl)-3-aza-6,6-difluorobicyclo[3.3.0]octane-2-carboxylate
  参考文献：
  名称：

  [EN] [C]-FUSED BICYCLIC PROLINE DERIVATIVES AND THEIR USE FOR TREATING ARTHRITIC CONDITIONS
  [FR] DERIVES DE PROLINE BICYCLIQUES 20041028US2003008861A1LIN LINUS S [US], et al20030109example 10, step C example 11, step A example 29, step c (starting material)X2,8XBERGMEIER S C ET AL: "Synthesis of Bicyclic Proline Analogs Using a Formal [3 + 2] Intramolecular Aziridine-Allylsilane Cycloaddition Reaction", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 55, no. 26, 25 June 1999 (1999-06-25), pages 8025 - 8038, XP004168571, ISSN: 0040-4020BERGMEIER S C ET ALSynthesis of Bicyclic Proline Analogs Using a Formal [3 + 2] Intramolecular Aziridine-Allylsilane Cycloaddition ReactionTETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL1999062555260040-40208025803845Scheme 7X2XDATABASE BEILSTEIN BEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DE; XP002288925, Database accession no. BRN:388906BEILSTEINBEILSTEIN INSTITUTE FOR ORGANIC CHEMISTRY, FRANKFURT-MAIN, DEBRN:388906AX4XMURAYAMA ET AL, YAKUGAKU ZASSHI, vol. 85, 1965, pages 765 - 769MURAYAMA ET ALYAKUGAKU ZASSHI196585765769WO0027808A1AVENTIS PHARMA GMBH [DE]20000518214814211517A1-9AWO03074048A1WARNER LAMBERT CO [US], et al2003091235253626PX1-9PXOTHMAN M ET AL: "New Fused Lactones from Indolizinediones via N-Acyliminium Ions", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 54, no. 30, 23 July 1998 (1998-07-23), pages 8737 - 8744, XP004124041, ISSN: 0040-4020OTHMAN M ET ALNew Fused Lactones from Indolizinediones via N-Acyliminium IonsTETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL1998072354300040-4020873787443A-EScheme 1X1XGUILLERM G ET AL: "Synthesis of Hydroxylated Pyrrolidines Derivatives as Potential Inhibitors of SAH/MTA Nucleosidase", TETRAHEDRON LETTERS, vol. 28, no. 5, 1987, pages 535 - 538, XP002288924GUILLERM G ET ALSynthesis of Hydroxylated Pyrrolidines Derivatives as Potential Inhibitors of SAH/MTA NucleosidaseTETRAHEDRON LETTERS19872855355384AScheme 2X1X

  摘要：

  本发明涉及一种[c]-融合的双环脯氨酸衍生物，或其药用可接受的盐；包括该化合物或其盐的药物组合物；以及治疗疾病的方法，包括但不限于预防或抑制关节软骨损伤，以及预防或治疗以关节软骨损伤、关节炎或关节疼痛为特征的疾病的方法。[c]-融合的双环脯氨酸衍生物是如上所述的I式化合物。以关节软骨损伤或关节疼痛为特征的疾病包括，例如，骨关节炎和类风湿性关节炎。类风湿性关节炎还以关节炎为特征。本发明还涉及合成和制备[c]-融合的双环脯氨酸衍生物或其药用可接受的盐的方法。

  公开号：

  WO2004092134A1

文献信息

• Bicyclic compounds and their use as excitatory amino acid receptor
  申请人：Eli Lilly and Company

  公开号：US05641798A1

  公开（公告）日：1997-06-24

  This invention provides novel bicyclic compounds which are useful as excitatory amino acid receptor antagonists and in the treatment of neurological disorders. This invention also provides intermediates useful in the synthesis of excitatory amino acid antagonists.

  本发明提供了一种新型双环化合物，可用作兴奋性氨基酸受体拮抗剂，并用于治疗神经系统疾病。本发明还提供了在合成兴奋性氨基酸拮抗剂时有用的中间体。
• Bicyclic intermediates for excitatory amino acid receptor antagonists
  申请人：Eli Lilly and Company

  公开号：US05491241A1

  公开（公告）日：1996-02-13

  This invention provides novel bicyclic compounds which are useful as excitatory amino acid receptor antagonists and in the treatment of neurological disorders. This invention also provides intermediates useful in the synthesis of excitatory amino acid antagonists.

  本发明提供了新型双环化合物，可用作兴奋性氨基酸受体拮抗剂，并用于治疗神经系统疾病。本发明还提供了在合成兴奋性氨基酸拮抗剂方面有用的中间体。