(R)-(-)-5-but-3-enyl-1-(toluene-4-sulfonyl)pyrrolidin-2-one | 853356-38-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-(-)-5-but-3-enyl-1-(toluene-4-sulfonyl)pyrrolidin-2-one
• 英文别名: (5R)-5-but-3-enyl-1-(p-tolylsulfonyl)pyrrolidin-2-one；(5R)-5-but-3-enyl-1-(4-methylphenyl)sulfonylpyrrolidin-2-one
• CAS: 853356-38-4
• 化学式: C₁₅H₁₉NO₃S
• 分子量: 293.387
• InChiKey: HGWWOIJMVWGJML-CYBMUJFWSA-N

物化性质

• 熔点：
  97 °C
• 沸点：
  421.1±38.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(-)-5-but-3-enyl-1-(toluene-4-sulfonyl)pyrrolidin-2-one 在 palladium diacetate 双(三甲基硅烷基)氨基钾 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.5h， 生成 (R)-(-)-5-but-3-enyl-1-(toluene-4-sulfonyl)-4,5-dihydro-1H-pyrrole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Remote Stereocontrol in the Nazarov Reaction:  A New Approach to the Core of Roseophilin

  摘要：

  Three different procedures are compared to obtain properly substituted divinyl ketones in which one of the double bonds is embedded in a five-membered heterocyclic structure and therefore suitable to produce cyclopenta-fused pyrrole derivatives by the acid-catalyzed Nazarov reaction. These, on treatment with TFA, afforded 2,4-cis-disubstituted 2,3,4,5-tetrahydro-1H-cyclopenta[b]pyrrol-6-ones with high stereocontrol. One of these Nazarov products was oxidized to the corresponding 4,5-dihydro-1H-cyclopenta[b]pyrrol-6-one derivative, thus obtaining an enantiopure key intermediate in the total synthesis of roseophilin.

  DOI：

  10.1021/jo0504058
• 作为产物：
  描述：

  (S)-(+)-5-羟甲基-2-吡咯烷酮对甲苯磺酸酯 在 正丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 为溶剂， 反应 6.0h， 生成 (R)-(-)-5-but-3-enyl-1-(toluene-4-sulfonyl)pyrrolidin-2-one
  参考文献：
  名称：

  Remote Stereocontrol in the Nazarov Reaction:  A New Approach to the Core of Roseophilin

  摘要：

  Three different procedures are compared to obtain properly substituted divinyl ketones in which one of the double bonds is embedded in a five-membered heterocyclic structure and therefore suitable to produce cyclopenta-fused pyrrole derivatives by the acid-catalyzed Nazarov reaction. These, on treatment with TFA, afforded 2,4-cis-disubstituted 2,3,4,5-tetrahydro-1H-cyclopenta[b]pyrrol-6-ones with high stereocontrol. One of these Nazarov products was oxidized to the corresponding 4,5-dihydro-1H-cyclopenta[b]pyrrol-6-one derivative, thus obtaining an enantiopure key intermediate in the total synthesis of roseophilin.

  DOI：

  10.1021/jo0504058

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。
• 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
• Compounds, Compositions and Methods
  申请人：Denali Therapeutics Inc.

  公开号：US20190300537A1

  公开（公告）日：2019-10-03

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