2,3-dihydroindolizin-5(1H)-one | 101773-62-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,3-dihydroindolizin-5(1H)-one
• 英文别名: 2,3-dihydro-1H-indolizin-5-one
• CAS: 101773-62-0
• 化学式: C₈H₉NO
• 分子量: 135.166
• InChiKey: BTHUPYAKEGMDNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3-dihydroindolizin-5(1H)-one 在 platinum(IV) oxide lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 17.0h， 生成 八氢吲嗪
  参考文献：
  名称：

  An Isomünchnone-Based Method for the Synthesis of Highly Substituted 2(1H)-Pyridones

  摘要：

  1-(Benzenesulfonyl-diazoacetyl)-pyrrolidin-2-one was prepared by a diazo transfer of 1-(benzenesulfonylacetyl)-pyrrolidin-2-one with p-acetamidobenzenesulfonyl azide and triethylamine. Treatment; of the diazoimide with a catalytic quantity of rhodium(II) acetate resulted in the formation of an isomunchnone dipole, which underwent bimolecular trapping with various dipolarophiles in high yield. The initially formed cycloadducts were not isolable or observed, as they all readily underwent ring opening to give the 3-hydroxy-2(1H)-pyridone ring system. The 3-hydroxy-2(1H)-pyridones were readily converted to the corresponding triflates, which function as suitable substrates in various types of palladium-catalyzed cross-coupling reactions. Commercial tetrakis(triphenylphoshine)palladium was found to be a particularly effective catalyst for the cross-coupling with aryl, vinyl, and acetylenic partners. An application of the method to the synthesis of the indolizidine alkaloid (+/-)-ipalbidine was carried out in eight steps in 17% overall yield. The angiotensin-converting enzyme inhibitor (-)-A58365A was also synthesized by a process based on the [3 + 2]-cycloaddition reaction of a phenylsulfonyl substituted isomunchnone intermediate. The starting material for this process was prepared from L-pyroglutamic acid and involved using a diazo phenylsulfonyl substituted pyrrolidine imide. Treatment of the diazoimide with Rh-2(OAc)(4) in the presence of methyl vinyl ketone afforded a 3-hydroxy-2-pyridone derivative, which was subsequently converted to the ACE inhibitor in six additional steps.

  DOI：

  10.1021/jo9911600
• 作为产物：
  描述：

  2-甲氧基吡啶 在 palladium on activated charcoal 、 氢溴酸 、 lithium 作用下， 以 环己烯 为溶剂， 反应 50.6h， 生成 2,3-dihydroindolizin-5(1H)-one
  参考文献：
  名称：

  Synthesis of indolizinones and a pyridoazepinone: a new method for the annulation of pyridinones

  摘要：

  DOI：

  10.1021/jo00362a006

文献信息

• [EN] Amide compounds and uses thereof<br/>[FR] COMPOSÉS AMIDES ET LEURS UTILISATIONS
  申请人：HUTCHISON MEDIPHARMA LTD

  公开号：WO2021197276A1

  公开（公告）日：2021-10-07

  Provided herein are novel amide compounds of formula (I), pharmaceutical compositions comprising same, methods for preparing same, and uses thereof, wherein the definition of each symbol is as described in the description.

  本文提供了化合物的新型酰胺化合物的公式(I)，包括相同的药物组合物，制备相同的方法以及它们的用途，其中每个符号的定义如描述中所述。
• [EN] SUBSTITUTED PYRIDONE DERIVATIVES AS PDE10 INHIBITORS<br/>[FR] DÉRIVÉS DE PYRIDONE SUBSTITUÉS UTILISÉS EN TANT QU'INHIBITEURS DE PDE10
  申请人：MERCK SHARP & DOHME

  公开号：WO2014081617A1

  公开（公告）日：2014-05-30

  The present invention is directed to substituted pyridinone compounds which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 10 (PDE10). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.

  本发明涉及取代吡啶酮化合物，其可用作治疗与磷酸二酯酶10（PDE10）相关的中枢神经系统疾病的治疗剂。本发明还涉及利用这些化合物治疗神经学和精神疾病，如精神分裂症、精神病或亨廷顿病，以及与纹状体功能不足或基底神经节功能障碍相关的疾病。
• [EN] PYRIDINONE AND PYRIMIDINONE DERIVATIVES AS FACTOR XIA INHIBITORS<br/>[FR] DÉRIVÉS DE PYRIDINONE ET DE PYRIMIDINONE COMME INHIBITEURS DU FACTEUR XIA
  申请人：ONO PHARMACEUTICAL CO

  公开号：WO2013093484A1

  公开（公告）日：2013-06-27

  The present invention provides compounds of the general formula (I), their salts and N- oxides, and solvates and prodrugs thereof (wherein the characters are as defined in the description). The compounds of the general formula (I) are inhibitors of Factor XIa, so that they are useful in the prevention of and/or therapy for thromboembolic diseases.

  本发明提供了一般式(I)的化合物，它们的盐和N-氧化物，以及它们的溶剂合物和前药（其中字符如描述中所定义）。一般式(I)的化合物是因子XIa的抑制剂，因此它们在预防和/或治疗血栓栓塞疾病方面是有用的。
• Carboxamide Compounds and Their Use
  申请人：Ben-Zeev Efrat

  公开号：US20100324035A1

  公开（公告）日：2010-12-23

  Chemokine receptor antagonists, in particular, compounds of Formula (I-A) that act as antagonists of the chemokine CCR2 receptor, including pharmaceutical compositions and uses thereof to treat or prevent diseases associated with monocyte accumulation, lymphocyte accumulation or leukocyte accumulation are described herein.

  化学因子受体拮抗剂，特别是化合物式(I-A)的拮抗剂，作为化学因子CCR2受体的拮抗剂，包括其药物组合物和用途，用于治疗或预防与单核细胞聚集、淋巴细胞聚集或白细胞聚集相关的疾病。
• [EN] CAMPTOTHECIN ANALOGS AS POTENT INHIBITORS OF HUMAN COLORECTAL CANCER
  申请人：RESEARCH TRIANGLE INSTITUTE

  公开号：WO1991005556A1

  公开（公告）日：1991-05-02

  (EN) A method for synthesizing camptothecin and camptothecin analogs using a novel hydroxyl-containing tricyclic intermediate and the camptothecin analogs produced by the process. The camptothecin analogs are effective inhibitors of topoisomerase I and show anti-leukemic and anti-tumor activity.(FR) L'invention se rapporte à un procédé de synthèse de camptothécine et d'analogues de camptothécine qui utilise un nouvel intermédiaire tricyclique contenant de l'hydroxyle, ainsi qu'aux analogues de camptothécine ainsi produits. Ces analogues de camptothécine sont des inhibiteurs efficaces de la topo-isomérase I et présentent des propriétés anti-leucémiques et anti-tumorales.

  (中文) 一种使用新型含羟基三环中间体合成喜树碱和喜树碱类似物的方法以及该过程产生的喜树碱类似物。这些喜树碱类似物是有效的拓扑异构酶I抑制剂，具有抗白血病和抗肿瘤活性。