trifluoromethanesulfonic acid 8-acetyl-5-oxo-1,2,3,5-tetrahydroindolizin-6-yl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: trifluoromethanesulfonic acid 8-acetyl-5-oxo-1,2,3,5-tetrahydroindolizin-6-yl ester
• 英文别名: (8-acetyl-5-oxo-2,3-dihydro-1H-indolizin-6-yl) trifluoromethanesulfonate
• 化学式: C₁₁H₁₀F₃NO₅S
• 分子量: 325.265
• InChiKey: DHZMBSYEKIHXBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-联苯硼酸 、 trifluoromethanesulfonic acid 8-acetyl-5-oxo-1,2,3,5-tetrahydroindolizin-6-yl ester 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 8-acetyl-6-(2-phenylphenyl)-2,3-dihydro-1H-indolizin-5-one
  参考文献：
  名称：

  铑催化形成的异蒙克酮合成2（1 H）-吡啶酮文库

  摘要：

  通过异丁烯与烯烃的偶极环加成反应，合成了2（1 H）-吡啶酮环系统。（1）使用不同的环化配偶体，随后使初始支架多样化，提供了4-hydroxy-2库（1 H）-吡啶酮。PubChem或MLSMR中都没有此环系统的示例

  DOI：

  10.1021/co400067q
• 作为产物：
  描述：

  1-(2-benzenesulfonyl-2-diazoacetyl)pyrrolidin-2-one 在 rhodium(II) acetate dimer 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 30.33h， 生成 trifluoromethanesulfonic acid 8-acetyl-5-oxo-1,2,3,5-tetrahydroindolizin-6-yl ester
  参考文献：
  名称：

  铑催化形成的异蒙克酮合成2（1 H）-吡啶酮文库

  摘要：

  通过异丁烯与烯烃的偶极环加成反应，合成了2（1 H）-吡啶酮环系统。（1）使用不同的环化配偶体，随后使初始支架多样化，提供了4-hydroxy-2库（1 H）-吡啶酮。PubChem或MLSMR中都没有此环系统的示例

  DOI：

  10.1021/co400067q

文献信息

• 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.
• Synthesis of a 2(1<i>H</i>)-Pyridone Library via Rhodium-Catalyzed Formation of Isomunchones
  作者：Subhasis De、Lu Chen、Shuxing Zhang、Scott R. Gilbertson

  DOI：10.1021/co400067q

  日期：2013.7.8

  Through the use of the dipolar cycloaddition of isomunchones with olefins the 2(1H)-pyridone ring system has been synthesized.(1) The use of different cyclization partners followed by diversification of the initial scaffold has provded libraries of 4-hydroxy-2(1H)-pyridones. There are no examples of this ring system in either PubChem or the MLSMR

  通过异丁烯与烯烃的偶极环加成反应，合成了2（1 H）-吡啶酮环系统。（1）使用不同的环化配偶体，随后使初始支架多样化，提供了4-hydroxy-2库（1 H）-吡啶酮。PubChem或MLSMR中都没有此环系统的示例