10-oxa-4-aza-tricyclo[5.2.1.0(2,6)]decane | 73611-42-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 10-oxa-4-aza-tricyclo[5.2.1.0(2,6)]decane
• 英文别名: 10-oxa-4-aza-tricyclo[5.2.1.0^2,6]decane；rac-(1R,2R,6S,7S)-10-oxa-4-azatricyclo[5.2.1.0~2,6~]decane；(3aR,4R,7S,7aS)-2,3,3a,4,5,6,7,7a-octahydro-1H-4,7-epoxyisoindole
• CAS: 73611-42-4
• 化学式: C₈H₁₃NO
• 分子量: 139.197
• InChiKey: GPLRZNABQAUBOS-SOSBWXJGSA-N

物化性质

• 沸点：
  223.7±33.0 °C(Predicted)
• 密度：
  1.100±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10-oxa-4-aza-tricyclo[5.2.1.0(2,6)]decane 在 2-碘酰基苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以71%的产率得到
  参考文献：
  名称：

  IBX-mediated oxidation of unactivated cyclic amines: application in highly diastereoselective oxidative Ugi-type and aza-Friedel–Crafts reactions

  摘要：

  第一个由o-碘代苯甲酸（IBX）介导的对未活化胺氧化生成亚胺的方法被描述。

  DOI：

  10.1039/c5ob01519g
• 作为产物：
  描述：

  7-oxabicyclo[2.2.1]heptane-2,3-dicarboximide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 以75%的产率得到10-oxa-4-aza-tricyclo[5.2.1.0(2,6)]decane
  参考文献：
  名称：

  IBX-mediated oxidation of unactivated cyclic amines: application in highly diastereoselective oxidative Ugi-type and aza-Friedel–Crafts reactions

  摘要：

  第一个由o-碘代苯甲酸（IBX）介导的对未活化胺氧化生成亚胺的方法被描述。

  DOI：

  10.1039/c5ob01519g

文献信息

• [EN] [C]-FUSED BICYCLIC PROLINE DERIVATIVES AND THEIR USE FOR TREATING ARTHRITIC CONDITIONS<br/>[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
  申请人：WARNER LAMBERT CO

  公开号：WO2004092134A1

  公开（公告）日：2004-10-28

  This invention relates to a compound which is [c]-fused bicyclic proline derivative, or a pharmaceutically acceptable salt thereof; a pharmaceutical composition comprising the compound or the salt thereof, and methods of treating diseases, including, but not limited to, methods of preventing or inhibiting joint cartilage damage and preventing or treating diseases characterized by joint cartilage damage, joint inflammation, or joint pain. The [c]-fused bicyclic proline derivatives are compounds of Formula I as described above. Diseases characterized by joint cartilage damage or joint pain include, for example, osteoarthritis and rheumatoid arthritis. Rheumatoid arthritis is also characterized by joint inflammation. This invention also relates to methods of synthesizing and preparing the [c]-fused bicyclic proline derivatives, or a pharmaceutically acceptable salt thereof.

  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。
• Stereoselective Monoamine Oxidase-Catalyzed Oxidative Aza-Friedel-Crafts Reactions of<i>meso</i>-Pyrrolidines in Aqueous Buffer
  作者：Corien de Graaff、Barry Oppelaar、Olivier Péruch、Christophe M. L. Vande Velde、Beatrice Bechi、Nicholas J. Turner、Eelco Ruijter、Romano V. A. Orru

  DOI：10.1002/adsc.201600038

  日期：2016.5.19

  We disclose the highly diastereoselective combination of monoamine oxidase‐catalyzed oxidation of meso‐pyrrolidines and aza‐Friedel–Crafts reactions in aqueous buffer to give valuable enantioenriched 2‐substituted pyrrolidines in a formal double CH activation process. A range of secondary as well as tertiary amines were shown to be suitable substrates for the biocatalytic oxidation and subsequent

  我们公开的单胺氧化酶催化的氧化的高度非对映组合内消旋氮杂Friedel-Crafts反应和-pyrrolidines在水性缓冲液中，得到对映体富集有价值2-取代的吡咯烷在正式双C  ħ激活过程。一系列仲胺和叔胺被证明是生物催化氧化和随后添加各种C-亲核试剂的合适底物。
• Synthesis and Characterization of Novel Bi- and Tricyclic α-Amino Acids
  作者：Matthew R. Johnson、Jolicia F. Gauuan、Cheng Guo、Peter R. Guzzo、Van-Duc Le、Rajesh A. Shenoy、James Hamby、Howard Roark、Michael Stier、John E. Mangette

  DOI：10.1080/00397911.2010.515354

  日期：2011.9.15

  As part of a medicinal chemistry collaboration, a number of novel bi- and tricyclic alpha-amino acids were prepared through various routes and characterized by H-1 nuclear Overhauser effect difference experiments. The syntheses provide a number of routes to access some highly substituted amino acid derivatives that have not been reported previously. It is envisaged that the chemistry described here could be applied to the synthesis of other unique substrates.
• IBX-mediated oxidation of unactivated cyclic amines: application in highly diastereoselective oxidative Ugi-type and aza-Friedel–Crafts reactions
  作者：C. de Graaff、L. Bensch、Matthijs J. van Lint、E. Ruijter、R. V. A. Orru

  DOI：10.1039/c5ob01519g

  日期：——

  The firsto-iodoxybenzoic acid (IBX) mediated oxidation of unactivated amines to imines is described.

  第一个由o-碘代苯甲酸（IBX）介导的对未活化胺氧化生成亚胺的方法被描述。