(5S)-5-but-3-en-1-ylpyrrolidin-2-one | 1109110-01-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (5S)-5-but-3-en-1-ylpyrrolidin-2-one
• 英文别名: (S)-5-(but-3-enyl)pyrrolidin-2-one；(5S)-5-but-3-enylpyrrolidin-2-one
• CAS: 1109110-01-1
• 化学式: C₈H₁₃NO
• 分子量: 139.197
• InChiKey: SYWCITUWIINULA-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-氯苯甲醚 、 (5S)-5-but-3-en-1-ylpyrrolidin-2-one 在 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.5h， 以75%的产率得到(5S,7aS)-5-(4-methoxybenzyl)hexahydropyrrolizin-3-one
  参考文献：
  名称：

  Diastereoselective Synthesis of Hexahydro-3H-pyrrolyzin-3-ones through Pd-Catalyzed Carboamination

  摘要：

  The reaction of readily available (5R)-5-but-3-en-1-ylpyrrolidin-2-one with aryl bromides, chlorides, or triflates in the presence of Pd-2(dba)(3), Xphos, and Cs2CO3 in 1,4-dioxane at 120 degrees C affords (5R,7aR)-5-aryl hexahydropyrrolizidin-3-ones in good to high yields through a diastereoselective carboamination reaction. Aryl iodides are less successful substrates than bromides and chlorides.

  DOI：

  10.1021/jo1002032
• 作为产物：
  描述：

  R-5-羟甲基-2-吡咯烷酮对甲苯磺酸酯 、 烯丙基溴化镁 以 四氢呋喃 为溶剂， 以68%的产率得到(5S)-5-but-3-en-1-ylpyrrolidin-2-one
  参考文献：
  名称：

  Selenium-promoted synthesis of enantiopure octahydroindolizines, hexahydro-1H-pyrrolizines and hexahydro-3H-pyrrolizin-3-ones

  摘要：

  Enantiomerically pure disubstituted pyrrolidines, recently synthesized from commercially available enantiomerically pure beta-aminoalcohol, were used as starting materials to synthesize enantiomerically pure hexahydro-1H-pyrrolizines and octahydroindolizine through a cyclization reaction promoted by N-(phenylseleno)phthalimide. Similarly, starting from enantiopure 5-(hydroxymethyl)pyrrolidin-2-ones, enantiopure hexahydro-3H-pyrrolizin-3-ones were obtained. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.10.006

文献信息

• [EN] COMPOUNDS, COMPOSITIONS AND METHODS<br/>[FR] COMPOSÉS, COMPOSITIONS ET MÉTHODES
  申请人：DENALI THERAPEUTICS INC

  公开号：WO2018107060A1

  公开（公告）日：2018-06-14

  The present disclosure relates generally to methods and compositions for preventing or arresting cell death and/or inflammation.

  本公开涉及用于预防或阻止细胞死亡和/或炎症的方法和组合物。
• Compounds, compositions and methods
  申请人：Denali Therapeutics Inc.

  公开号：US11072618B2

  公开（公告）日：2021-07-27

  The present disclosure relates generally to methods and compositions for preventing or arresting cell death and/or inflammation.

  本公开总体上涉及预防或阻止细胞死亡和/或炎症的方法和组合物。
• Novel synthesis of CP-734432, an EP4 agonist, using Sharpless asymmetric dihydroxylation
  作者：Sajiv K. Nair、Jean J. Matthews、Stephan J. Cripps、Chunrong Ma、Elena Z. Dovalsantos、Alan W. Grubbs、Neal W. Sach、Wolter ten Hoeve、Han Koster、Erik J. Flahive、Steven P. Tanis、Matt Renner、Jim van Wiltenburg

  DOI：10.1016/j.tetlet.2009.12.092

  日期：2010.3

  A novel and efficient asymmetric route to CP-734432, a lactam analog of PGE2, that shows selective agonism against the EP4 receptor subtype, is reported herein. The key steps include a Heck coupling to introduce the aryl ring at C-16 and a highly diastereoselective Sharpless asymmetric dihydroxylation to set the C-15 center. (C) 2009 Elsevier Ltd. All rights reserved.
• COMPOUNDS, COMPOSITIONS AND METHODS
  申请人：Denali Therapeutics Inc.

  公开号：EP3552017A1

  公开（公告）日：2019-10-16
• COMPOUNDS USEFUL AS RIPK1 INHIBITORS
  申请人：Denali Therapeutics Inc.

  公开号：EP3552017B1

  公开（公告）日：2022-02-23