5-(ethoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyl-1H-pyrrole-3-carboxylic acid | 1433997-83-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-(ethoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyl-1H-pyrrole-3-carboxylic acid
• 英文别名: 5-ethoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1H-pyrrole-3-carboxylic acid
• CAS: 1433997-83-1
• 化学式: C₂₁H₁₉NO₅
• 分子量: 365.386
• InChiKey: VPKURIRLECECDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  88.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (1Z)-2-偶氮基-1-乙氧基-3-氧代-3-苯基-1-丙烯-1-醇 、 3-(4-甲基苯基)-2H-吖丙因-2-甲醛 在 dirhodium tetraacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 以12%的产率得到5-(ethoxycarbonyl)-2-(4-methoxyphenyl)-4-phenyl-1H-pyrrole-3-carboxylic acid
  参考文献：
  名称：

  Rh2(OAc)4-catalyzed reaction of α-diazocarbonyl compounds with 2-carbonyl-substituted 2H-azirines

  摘要：

  The Rh-2(OAc)(4)-catalyzed reaction of 2H-azirine-2-carbaldehydes with dimethyl diazomalonate proceeds via azirinium ylide formation, isomerization to 2-azabuta-1,3-dienes followed by 1,6-pi-electrocyclization to give 2H-1,3-oxazines. According to DFT-calculations ring opening of azirinium ylides should occur stereoselectively to give 2-azadienes with the C=C bond exclusively in the Z configuration. Changing a formyl group for an acetyl group in the azirine leads to a lowering of stereoselectivity and the formation of azadienes with an E configuration of the C=C bond was observed. The reaction of 2-acy1-2-diazoacetates with 2H-azirine-2-carbaldehydes proceeds similarly, but the 2-acetyl-substituted 2H-1,3-oxazines formed are unstable under chromatographic purification and rearrange easily into pyrrole derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.04.022

文献信息

• Rh2(OAc)4-catalyzed reaction of α-diazocarbonyl compounds with 2-carbonyl-substituted 2H-azirines
  作者：Kirill V. Zavyalov、Mikail S. Novikov、Alexander F. Khlebnikov、Dmitry S. Yufit

  DOI：10.1016/j.tet.2013.04.022

  日期：2013.6

  The Rh-2(OAc)(4)-catalyzed reaction of 2H-azirine-2-carbaldehydes with dimethyl diazomalonate proceeds via azirinium ylide formation, isomerization to 2-azabuta-1,3-dienes followed by 1,6-pi-electrocyclization to give 2H-1,3-oxazines. According to DFT-calculations ring opening of azirinium ylides should occur stereoselectively to give 2-azadienes with the C=C bond exclusively in the Z configuration. Changing a formyl group for an acetyl group in the azirine leads to a lowering of stereoselectivity and the formation of azadienes with an E configuration of the C=C bond was observed. The reaction of 2-acy1-2-diazoacetates with 2H-azirine-2-carbaldehydes proceeds similarly, but the 2-acetyl-substituted 2H-1,3-oxazines formed are unstable under chromatographic purification and rearrange easily into pyrrole derivatives. (C) 2013 Elsevier Ltd. All rights reserved.