1-(phenylsulfonylacetyl)pyrrolidin-2-one | 907969-47-5

• 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: 1-(phenylsulfonylacetyl)pyrrolidin-2-one
• 英文别名: 1-(2-(Phenylsulfonyl)acetyl)pyrrolidin-2-one；1-[2-(benzenesulfonyl)acetyl]pyrrolidin-2-one
• CAS: 907969-47-5
• 化学式: C₁₂H₁₃NO₄S
• 分子量: 267.306
• InChiKey: IJGGKBMTKCJJEX-UHFFFAOYSA-N

物化性质

• 沸点：
  512.1±42.0 °C(Predicted)
• 密度：
  1.380±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  79.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(phenylsulfonylacetyl)pyrrolidin-2-one 在 4-乙酰氨基苯磺酰叠氮 、 三乙胺 作用下， 以 乙腈 为溶剂， 以85%的产率得到1-(2-benzenesulfonyl-2-diazoacetyl)pyrrolidin-2-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
• 作为产物：
  描述：

  (苯磺酰)乙酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 苯 为溶剂， 反应 10.0h， 生成 1-(phenylsulfonylacetyl)pyrrolidin-2-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] PYRIDINYL BASED APOPTOSIS SIGNAL-REGULATION KINASE INHIBITORS<br/>[FR] INHIBITEURS DE KINASE DE RÉGULATION DU SIGNAL APOPTOTIQUE À BASE DE PYRIDINYLE
  申请人：FRONTHERA U S PHARMACEUTICALS LLC

  公开号：WO2018151830A1

  公开（公告）日：2018-08-23

  Apoptosis signal-regulating kinase 1 (ASK1) activation and signaling have been reported to play an important role in a broad range of diseases including neurodegenerative, cardiovascular, inflammatory, autoimmunity and metabolic disorders. Disclosed herein is the synthesis of pyridinyl derived therapeutic agents that function as inhibitors of ASK 1 as well as their pharmaceutical compositions and methods of use.

  细胞凋亡信号调节激酶1（ASK1）的激活和信号传导据报道在包括神经退行性、心血管、炎症、自身免疫和代谢紊乱等广泛疾病中发挥重要作用。本文披露了一种以吡啶基衍生的治疗剂的合成，其作为ASK1的抑制剂以及它们的药物组合物和使用方法。
• Photochemical Oximesulfonylation of Alkenes Using Sulfonyl‐Oxime‐Ethers as Bifunctional Reagents
  作者：Jayanta Dey、Nayan Banerjee、Swikriti Daw、Joyram Guin

  DOI：10.1002/anie.202312384

  日期：2023.10.26

  An efficient metal free photochemical method for regioselective incorporation of oxime ether and sulfonyl functionality to olefin using sulfonyl-oxime-ethers as bifunctional reagents is demonstrated. The process exhibits a wide substrate scope providing rapid access to 1,2-oximesulfonylated products in good to excellent yields and diastereoselectivity.

  展示了一种使用磺酰基肟醚作为双官能试剂将肟醚和磺酰基官能团区域选择性结合到烯烃中的有效无金属光化学方法。该工艺具有广泛的底物范围，可快速获得 1,2-肟磺酰化产物，并具有良好至优异的产率和非对映选择性。
• New Synthetic Route to 2-Pyridones and Its Application toward the Synthesis of (±)-Ipalbidine
  作者：Scott M. Sheehan、Albert Padwa

  DOI：10.1021/jo961690l

  日期：1997.2.1
• An Isomünchnone-Based Method for the Synthesis of Highly Substituted 2(1<i>H</i>)-Pyridones
  作者：Albert Padwa、Scott M. Sheehan、Christopher S. Straub

  DOI：10.1021/jo9911600

  日期：1999.11.1

  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.