phenylmethyl 3-(8-hydroxy-5-oxo-3-(benzyloxycarbonyl)-1,2,3-trihydroindolizin-6-yl)propanoate | 229640-43-1

• 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: phenylmethyl 3-(8-hydroxy-5-oxo-3-(benzyloxycarbonyl)-1,2,3-trihydroindolizin-6-yl)propanoate
• 英文别名: benzyl (3S)-8-hydroxy-5-oxo-6-(3-oxo-3-phenylmethoxypropyl)-2,3-dihydro-1H-indolizine-3-carboxylate
• CAS: 229640-43-1
• 化学式: C₂₆H₂₅NO₆
• 分子量: 447.488
• InChiKey: WBAFAGFQXGXGJA-QFIPXVFZSA-N

物化性质

• 沸点：
  636.6±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  94.83
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  phenylmethyl 3-(8-hydroxy-5-oxo-3-(benzyloxycarbonyl)-1,2,3-trihydroindolizin-6-yl)propanoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以96%的产率得到(-)-A58365A
  参考文献：
  名称：

  Total synthesis of the angiotensin-converting enzyme inhibitor A58365A: On the use of pyroglutamate as a chiral educt

  摘要：

  DOI：

  10.1016/s0040-4039(01)80464-0
• 作为产物：
  描述：

  L-焦谷氨酸甲酯 在 palladium on activated charcoal 三氟化硼乙醚 、 氢气 、 potassium hydrogencarbonate 、 三乙胺 、 间氯过氧苯甲酸 、 N,N'-二环己基碳二亚胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 甲醇 、 甲苯 、 苯 为溶剂， 反应 12.0h， 生成 phenylmethyl 3-(8-hydroxy-5-oxo-3-(benzyloxycarbonyl)-1,2,3-trihydroindolizin-6-yl)propanoate
  参考文献：
  名称：

  Total synthesis of the angiotensin-converting enzyme inhibitor A58365A: On the use of pyroglutamate as a chiral educt

  摘要：

  DOI：

  10.1016/s0040-4039(01)80464-0

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 the Angiotensin Converting Enzyme Inhibitor (−)-A58365A via an Cycloaddition Reaction
  作者：Christopher S. Straub、Albert Padwa

  DOI：10.1021/ol9905497

  日期：1999.7.1

  The angiotensin converting enzyme inhibitor (-)-A58365A (1) was 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.
• FANG, FRANCIS G.;DANISHEFSKY, SAMUEL J., TETRAHEDRON LETT., 30,(1989) N8, C. 3621-3624
  作者：FANG, FRANCIS G.、DANISHEFSKY, SAMUEL J.

  DOI：——

  日期：——