methyl 4-(2-methoxyphenyl)-2-oxo-4-(1H-pyrrol-2-yl)butanoate | 960382-70-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 4-(2-methoxyphenyl)-2-oxo-4-(1H-pyrrol-2-yl)butanoate
• CAS: 960382-70-1
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: LZXDHRMJOWGOMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(2-methoxyphenyl)-2-oxo-4-(1H-pyrrol-2-yl)butanoate 以 四氯化碳 为溶剂， 反应 6.0h， 以100%的产率得到methyl 3-hydroxy-1-(2-methoxyphenyl)-2,3-dihydro-1H-pyrrolizine-3-carboxylate
  参考文献：
  名称：

  Copper Triflate Catalyzed Regioselective Alkylation of Pyrrole: Conversion of 2-Alkylated Pyrroles to Novel Pyrrolizine Derivatives by Self-Cyclization

  摘要：

  Metal triflate catalyzed addition reaction of pyrrole to methyl 2-oxo-4-phenylbut-3-enoate and substituted derivatives generated the related novel alkylated pyrroles regioselectively at C(2) of pyrrole. Among the studied metal triflates, Cu(OTf)(2) was found to be more effective in the addition reaction. The synthesized methyl 2-oxo-4-phenyl-4-(1H-pyrrole-2-yl)butanoate esters underwent self-cyclization by heating and yielded the corresponding methyl 3-hydroxy-1-phenyl-2,3-dihydro-1H-pyrrolizine-3-carboxylate and substituted derivatives. This reaction procedure allowed easy access to pyrrolizine structure in mild reaction conditions.

  DOI：

  10.3987/com-07-11137
• 作为产物：
  描述：

  吡咯 、 (E)-methyl 4-(2-methoxyphenyl)-2-oxobut-3-enoate 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 为溶剂， 以45%的产率得到methyl 4-(2-methoxyphenyl)-2-oxo-4-(1H-pyrrol-2-yl)butanoate
  参考文献：
  名称：

  Copper Triflate Catalyzed Regioselective Alkylation of Pyrrole: Conversion of 2-Alkylated Pyrroles to Novel Pyrrolizine Derivatives by Self-Cyclization

  摘要：

  Metal triflate catalyzed addition reaction of pyrrole to methyl 2-oxo-4-phenylbut-3-enoate and substituted derivatives generated the related novel alkylated pyrroles regioselectively at C(2) of pyrrole. Among the studied metal triflates, Cu(OTf)(2) was found to be more effective in the addition reaction. The synthesized methyl 2-oxo-4-phenyl-4-(1H-pyrrole-2-yl)butanoate esters underwent self-cyclization by heating and yielded the corresponding methyl 3-hydroxy-1-phenyl-2,3-dihydro-1H-pyrrolizine-3-carboxylate and substituted derivatives. This reaction procedure allowed easy access to pyrrolizine structure in mild reaction conditions.

  DOI：

  10.3987/com-07-11137

文献信息

• Copper Triflate Catalyzed Regioselective Alkylation of Pyrrole: Conversion of 2-Alkylated Pyrroles to Novel Pyrrolizine Derivatives by Self-Cyclization
  作者：Canan Unaleroglu、Sertan Aytac、Baris Temelli

  DOI：10.3987/com-07-11137

  日期：——

  Metal triflate catalyzed addition reaction of pyrrole to methyl 2-oxo-4-phenylbut-3-enoate and substituted derivatives generated the related novel alkylated pyrroles regioselectively at C(2) of pyrrole. Among the studied metal triflates, Cu(OTf)(2) was found to be more effective in the addition reaction. The synthesized methyl 2-oxo-4-phenyl-4-(1H-pyrrole-2-yl)butanoate esters underwent self-cyclization by heating and yielded the corresponding methyl 3-hydroxy-1-phenyl-2,3-dihydro-1H-pyrrolizine-3-carboxylate and substituted derivatives. This reaction procedure allowed easy access to pyrrolizine structure in mild reaction conditions.