2-甲基-1,4,5,6-四氢环戊烯并[b]吡咯 | 92705-53-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2-甲基-1,4,5,6-四氢环戊烯并[b]吡咯
• 英文名称: 2-methyl 1,4,5,6-tetrahydrocyclopenta[b]pyrrole
• 英文别名: 4,5-dihydro-2-methyl-cyclopentapyrrole；2-Methyl-1,4,5,6-tetrahydrocyclopenta[b]pyrrole
• CAS: 92705-53-8
• 化学式: C₈H₁₁N
• 分子量: 121.182
• InChiKey: FPTVEBZXBUYUOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  2-azidocyclopentanone 在 四氯化钛 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 2-甲基-1,4,5,6-四氢环戊烯并[b]吡咯
  参考文献：
  名称：

  Domino “Staudinger/Semi-Aza-Wittig/Fragmentation” Reactions of γ-Azido-β-hydroxyketones

  摘要：

  Treatment of gamma-azido-beta-hydroxyketones with triphenylphosphine resulted, depending on the structural features of the starting materials, in a domino "Staudinger/semi-aza-Wittig/fragmentation" reaction rather than a normal aza-Wittig reaction. 2-Azido-1-hydroxy-1-(2,4-dioxoalkyl)cyclopentanes, readily available by condensation of 1,3-dicarbonyl dianions with 2-azidocyclopentanone, proved to be optimal starting materials for these reactions which afforded 1-(1,3-dioxoalkyl)amino-2-(alkylidene)cyclopentanes.

  DOI：

  10.1021/jo060891e

文献信息

• Nitrogen Fixation: Synthesis of Heterocycles Using Molecular Nitrogen as a Nitrogen Source
  作者：Miwako Mori、Masaya Akashi、Masanori Hori、Katsutoshi Hori、Mayumi Nishida、Yoshihiro Sato

  DOI：10.1246/bcsj.77.1655

  日期：2004.9

  Nitrogen fixation using transition metals is a fascinating process. We have already reported on the incorporation of molecular nitrogen into organic compounds using a titanium–nitrogen complex reported by Yamamoto. We developed a novel titanium-catalyzed nitrogenation procedure using TiCl4 in the presence of an excess amount of Li and TMSCl. In this reaction, a 1 atm pressure of nitrogen gas can be used and the reaction proceeds at room temperature. The procedure is very simple. A THF solution of TiCl4 or Ti(OiPr)4 (1 equiv.), Li (10 equiv.), and TMSCl (10 equiv.) was stirred under an atmosphere of nitrogen at room temperature overnight to give titanium–nitrogen complexes. Although the structures of the titanium–nitrogen complexes have not yet been determined, they would consist of N(TMS)3, X2TiN(TMS)2, and XTi=NTMS. Using this procedure, various heterocycles, such as indole, quinoline, pyrrole, pyrrolizine, and indolizine derivatives, could be synthesized from molecular nitrogen in good-to-moderate yields as a stoichiometric reaction based on a titanium complex by a one-pot reaction. Furthermore, monomorine I and pumiliotoxin C were synthesized from molecular nitrogen as a nitrogen source. This procedure was further extended for the syntheses of heterocycles using a catalytic amount of titanium complex; also, indole and pyrrole derivatives were obtained in high yields.

  过渡金属固氮是一个迷人的过程。我们之前已经报道过使用Yamamoto报道的钛-氮配合物将分子氮引入有机化合物的方法。我们开发了一种新的钛催化氮化过程，使用TiCl4在过量Li和TMSCl的存在下进行。在这种反应中，可以使用1大气压的氮气，反应在室温下进行。这个过程非常简单。将TiCl4或Ti(OiPr)4（1 equiv.）、Li（10 equiv.）和TMSCl（10 equiv.）的THF溶液在氮气气氛下在室温下搅拌过夜，得到钛-氮配合物。尽管钛-氮配合物的结构尚未确定，但它们可能由N(TMS)3、X2TiN(TMS)2和XTi=NTMS组成。使用这种方法，可以通过钛配合物作为定量反应的单锅反应，以良好至中等的收率合成各种杂环化合物，如吲哚、喹啉、吡咯、吡咯啉和吲哚啉衍生物。此外，使用分子氮作为氮源合成了monomorine I和pumiliotoxin C。这种方法进一步扩展，用于使用催化量的钛配合物合成杂环化合物；此外，以高收率获得了吲哚和吡咯衍生物。
• Benzyne, cyclohexyne, and 3-azacyclohexyne and the problem of cycloalkyne versus cycloalkylideneketene genesis
  作者：Curt. Wentrup、Rodney. Blanch、Horst. Briehl、Gerhard. Gross

  DOI：10.1021/ja00214a034

  日期：1988.3

  Benzyne, cyclohexyne, and 3-azacyclohexyne have been obtained by flash vacuum pyrolysis of phthalic anhydride, 4-cyclopentylidene-3-methylisoxazol-5(4H)-one (34), and 3-methyl-4-(2-pyrrolidinylidene)isoxazol-5(4H)-one (37), respectively, isolated at 77 K and observed by IR spectroscopy. Trapping and fragmentation reactions are described, and the implications for the mechanism of benzyne formation from

  苯、环己炔和 3-氮杂环己炔已通过邻苯二甲酸酐、4-环戊基-3-甲基异恶唑-5(4H)-酮 (34) 和 3-甲基-4-(2-吡咯烷亚基)异恶唑的快速真空热解获得-5(4H)-one (37) 分别在 77 K 下分离并通过红外光谱观察。描述了捕集和断裂反应，并讨论了邻苯二甲酸酐通过环戊二烯亚基乙烯酮 (9) 形成苄的机理。
• 5-5-Membered fused heterocyclic compound and use thereof as HCV polymerase inhibitor
  申请人：Mizojiri Ryo

  公开号：US20090036444A1

  公开（公告）日：2009-02-05

  The present invention relates to a fused ring compound represented by the following formula [I] wherein each symbol is as defined in the specification, or a pharmaceutically acceptable a salt thereof, and a hepatitis C virus (HCV) polymerase inhibitor and a therapeutic agent for hepatitis C containing this compound. The compound of the present invention shows an anti-HCV activity based on the HCV polymerase inhibitory activity, and useful as an agent for the prophylaxis or treatment of hepatitis C.

  本发明涉及一种由以下式[I]表示的融合环化合物，其中每个符号如规范中所定义，或其药学上可接受的盐，以及一种丙型肝炎病毒（HCV）聚合酶抑制剂和治疗丙型肝炎的药物，本发明的化合物基于HCV聚合酶抑制活性具有抗HCV活性，是一种预防或治疗丙型肝炎的药剂。
• INHIBITORS OF D-AMINO ACID OXIDASE
  申请人：Heffernan Michele L. R.

  公开号：US20100029737A1

  公开（公告）日：2010-02-04

  The present invention provides novel inhibitors of the enzyme D-amino acid oxidase. The compounds of the invention are useful for treating or preventing diseases and/or condition, wherein modulation of D-serine levels, and/or its oxidative products, is effective in ameliorating symptoms. The invention further provides methods of enhancing learning, memory and/or cognition. For example, the invention provides methods for treating or preventing loss of memory and/or cognition associated with neurodegenerative diseases, such as Alzheimer's disease. The invention further provides methods for preventing loss of neuronal function characteristic of neurodegenerative diseases. In addition, methods are provided for the treatment or prevention of neuropsychiatric diseases (e.g., schizophrenia) and for the treatment or prevention of pain and ataxia.

  本发明提供了新型D-氨基酸氧化酶酶的抑制剂。本发明的化合物可用于治疗或预防疾病和/或症状，其中调节D-丝氨酸水平和/或其氧化产物对缓解症状有效。本发明还提供了增强学习，记忆和/或认知的方法。例如，本发明提供了用于治疗或预防神经退行性疾病（如阿尔茨海默病）相关的记忆和/或认知丧失的方法。本发明还提供了预防神经退行性疾病特征性神经元功能丧失的方法。此外，还提供了用于治疗或预防神经精神疾病（例如，精神分裂症）和用于治疗或预防疼痛和共济失调的方法。
• 4-Alkylideneisoxazol-5-ones. Synthesis, tautomerism, and rearrangement to pyrroles
  作者：Hans Joachim Wollweber、Curt Wentrup

  DOI：10.1021/jo00212a007

  日期：1985.6

表征谱图