hexahydroindolizin-5(1H)-one | 32537-55-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: hexahydroindolizin-5(1H)-one
• 英文别名: 5-oxoindolizidine；5-indolizidinone；hexahydro-indolizin-5-one；1-Azabicyclo<4.3.0>nonanon-(9)；Hexahydro-5(1H)-indolizinon；2,3,6,7,8,8a-hexahydro-1H-indolizin-5-one
• CAS: 32537-55-6
• 化学式: C₈H₁₃NO
• 分子量: 139.197
• InChiKey: RDPDXQHZOLPNMZ-UHFFFAOYSA-N

物化性质

• 沸点：
  256.8±7.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  hexahydroindolizin-5(1H)-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 八氢吲嗪
  参考文献：
  名称：

  Tetrahydropyridones via intramolecular ureidomercuration

  摘要：

  DOI：

  10.1016/s0040-4039(00)81313-1
• 作为产物：
  描述：

  1-(2-benzenesulfonyl-2-diazoacetyl)pyrrolidin-2-one 在 platinum(IV) oxide rhodium(II) acetate dimer 、 甲酸 、 bis(triphenylphosphine) palladium (Il) acetate 、 氢溴酸 、 氢气 、 三乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 20.0~135.0 ℃ 、620.53 kPa 条件下， 反应 37.0h， 生成 hexahydroindolizin-5(1H)-one
  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

文献信息

• [EN] ARYL HETEROBICYCLIC COMPOUNDS AS KV1.3 POTASSIUM SHAKER CHANNEL BLOCKERS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ARYLÉS EN TANT QUE BLOQUEURS DU CANAL POTASSIQUE SHAKER KV1.3
  申请人：DE SHAW RES LLC

  公开号：WO2021071832A1

  公开（公告）日：2021-04-15

  A compound of Formula (I), or a pharmaceutically acceptable salt thereof, is described, where the substituents are as defined herein. Pharmaceutical compositions including the same and method of using the same are also described.

  描述了化合物式(I)或其药用可接受的盐，其中取代基如本文所定义。还描述了包括该化合物的药物组合物以及使用该化合物的方法。
• In Situ Generation and Intramolecular Schmidt Reaction of Keto Azides in a Microwave-Assisted Flow Format
  作者：Thomas O. Painter、Paul D. Thornton、Mario Orestano、Conrad Santini、Michael G. Organ、Jeffrey Aubé

  DOI：10.1002/chem.201100768

  日期：2011.8.22

  Go with the flow! A method for conversion of keto halides to lactams by means of sequential azidation and intramolecular Schmidt reaction in a combined flow format is described (see scheme; MWI=microwave irradiation, TFA=trifluoroacetic acid).

  顺其自然！描述了通过连续叠氮化和分子内施密特反应以组合流动形式将酮卤化物转化为内酰胺的方法（参见方案；MWI=微波辐射，TFA=三氟乙酸）。
• Hypervalent organoiodine reagents in the transannular functionalisation of medium-sized lactams: synthesis of 1-azabicyclo compounds
  作者：R. L. Dorta、C. G. Francisco、E. Suárez

  DOI：10.1039/c39890001168

  日期：——

  produced by photolysis of medium-sized lactams 7-heptanelactam (1), 8-octanelactam (3), and 9-nonanelactam (6) in the presence of (diacetoxyiodo)benzene (DIB) and iodine, undergo transannular hydrogen abstraction to afford intermolecularly functionalised compounds such as oxoindolizidines (4) and (5) and the 1-azabicyclo[5.3.0]decan-2-one (7) that are obtained in high yield from lactams (3) and (6), respectively

  由中等大小的内酰胺7-庚内酰胺（1），8-辛内酰胺（3）和9-壬内酰胺（6）在（二乙酰氧基碘）苯（DIB）和碘存在下进行光解而制得的酰胺基自由基中间体提取氢得到分子间官能化的化合物，例如氧代吲哚并（4）和（5）和1-氮杂双环[5.3.0] decan-2-one（7），它们是从内酰胺（3）和（6）高产率获得的， 分别。
• Intramolecular Schmidt reactions of alkyl azides with ketals and enol ethers
  作者：Craig J. Mossman、Jeffrey Aubé

  DOI：10.1016/0040-4020(96)00037-3

  日期：1996.3

  The ketals or enol ethers of 1,5-azidoketones were converted into lactams using a two-stage process. Treatment of the ketals and enol ethers with acid (trifluoroacetic acid, triflic acid, or trimethylsilyl triflate) afforded an oxonium ion which reacted with the tethered azide to give a 1,1-azido-alkoxy intermediate. Bond reorganization led to an iminium ether that was reacted with sodium iodide in

  使用两步法将1，5-叠氮酮的缩酮或烯醇醚转化为内酰胺。用酸（三氟乙酸，三氟甲磺酸或三甲基三氟甲磺酸酯）处理缩酮和烯醇醚，得到氧鎓离子，其与束缚的叠氮化物反应，得到1，1-叠氮基-烷氧基中间体。键的重组产生了亚胺醚，该亚胺醚与碘化钠在丙酮中反应以暴露出酰胺产物。据报道，使用二甲基或二乙基缩酮，有七个分子内实例的收率在68％至≥95％之间。还描述了使用1，3-二氧戊环的尝试和一个分子间的实例。
• HETEROCYCLIC COMIPOUND AS CDK-HDAC DUAL PATHWAY INHIBITOR
  申请人：Hangzhou Innogate Pharma Co., Ltd.

  公开号：US20220024916A1

  公开（公告）日：2022-01-27

  The invention provides compounds of formula (I) as shown below, as well as pharmaceutically acceptable salts, hydrates or solvates thereof. The invention also provides pharmaceutical compositions of these compounds, methods for their preparation, and their use in the treatment of diseases and disorders (including cancers).

  该发明提供了如下所示的式（I）的化合物，以及其药学上可接受的盐、水合物或溶剂化合物。该发明还提供了这些化合物的药物组合物、其制备方法，以及它们在治疗疾病和疾病（包括癌症）中的应用。