(+/-)-methyl 2-benzyloxymethyl-1-(4-methoxybenzyl)-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylate | 1002321-53-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+/-)-methyl 2-benzyloxymethyl-1-(4-methoxybenzyl)-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylate
• 英文别名: Methyl 1-[(4-methoxyphenyl)methyl]-5-oxo-2-(phenylmethoxymethyl)pyrrole-2-carboxylate
• CAS: 1002321-53-0
• 化学式: C₂₂H₂₃NO₅
• 分子量: 381.428
• InChiKey: FUJSOYAESBTRBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-methyl 2-benzyloxymethyl-1-(4-methoxybenzyl)-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylate 、 N-methylnitrone 以 甲苯 为溶剂， 反应 3.0h， 以58%的产率得到(3aRS,6RS,6aSR)-methyl 6-[(benzyloxy)methyl]-5-(4-methoxybenzyl)-2-methyl-4-oxohexahydro-2H-pyrrolo[3,4-d]isoxazole-6-carboxylate
  参考文献：
  名称：

  Nitrone [2+3]-Cycloadditions in Stereocontrolled Synthesis of a Potent Proteasome Inhibitor:  (−)-Omuralide

  摘要：

  A new stereocontrolled synthetic route to omuralide has been developed from methyl pyroglutamate. This route involves regio- and stereoselective N-methylnitrone 1,3-dipolar cycloadditions to appropriate pyrrolinones, beta-eliminations, and highly selective hydrogenations as the main steps.

  DOI：

  10.1021/jo701968d
• 作为产物：
  描述：

  (+/-)-methyl 2-benzyloxymethyl-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylate 、 4-甲氧基溴苄 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以88%的产率得到(+/-)-methyl 2-benzyloxymethyl-1-(4-methoxybenzyl)-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Nitrone [2+3]-Cycloadditions in Stereocontrolled Synthesis of a Potent Proteasome Inhibitor:  (−)-Omuralide

  摘要：

  A new stereocontrolled synthetic route to omuralide has been developed from methyl pyroglutamate. This route involves regio- and stereoselective N-methylnitrone 1,3-dipolar cycloadditions to appropriate pyrrolinones, beta-eliminations, and highly selective hydrogenations as the main steps.

  DOI：

  10.1021/jo701968d