methyl (E)-2-benzylidene-3-oxo-3-(1H-pyrrol-2-yl)propanoate | 1184171-67-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: methyl (E)-2-benzylidene-3-oxo-3-(1H-pyrrol-2-yl)propanoate
• 英文别名: Methyl (e)-2-benzylidene-3-oxo-3-(1h-pyrrol-2-yl) propanoate；methyl (E)-3-phenyl-2-(1H-pyrrole-2-carbonyl)prop-2-enoate
• CAS: 1184171-67-2
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: CEWKZFHSKFEGQY-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (E)-2-benzylidene-3-oxo-3-(1H-pyrrol-2-yl)propanoate 在 alumina-supported iron(III) perchlorate 作用下， 反应 5.0h， 以98%的产率得到methyl 1,4,5,6-tetrahydro-6-oxo-4-phenylcyclopenta[b]pyrrole-5-carboxylate
  参考文献：
  名称：

  Development of sequential type iron salt-catalyzed Nazarov/Michael reaction in an ionic liquid solvent system

  摘要：

  已证明在离子液体中使用5 mol% Fe(ClO4)3·Al2O作为催化剂进行吡咯衍生物的序贯类型一锅Nazarov/Michael反应。我们成功地在五次反应中获得了4,5-二氢环戊[b]吡咯-6(1H)-酮衍生物，且在没有任何催化剂添加的情况下，使用离子液体[bmim][NTf2]作为溶剂体系，产率良好。

  DOI：

  10.1007/s11426-012-4629-3
• 作为产物：
  描述：

  2-乙酰基吡咯 在 哌啶 、 potassium hydride 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 反应 8.5h， 生成 methyl (E)-2-benzylidene-3-oxo-3-(1H-pyrrol-2-yl)propanoate
  参考文献：
  名称：

  Development of sequential type iron salt-catalyzed Nazarov/Michael reaction in an ionic liquid solvent system

  摘要：

  已证明在离子液体中使用5 mol% Fe(ClO4)3·Al2O作为催化剂进行吡咯衍生物的序贯类型一锅Nazarov/Michael反应。我们成功地在五次反应中获得了4,5-二氢环戊[b]吡咯-6(1H)-酮衍生物，且在没有任何催化剂添加的情况下，使用离子液体[bmim][NTf2]作为溶剂体系，产率良好。

  DOI：

  10.1007/s11426-012-4629-3

文献信息

• Development of Solvent-Driven Iron-Catalyzed Reactions
  作者：Toshiyuki Itoh

  DOI：10.3987/rev-16-842

  日期：——

  The possibility of solvent-driven iron-catalyzed reactions has been investigated using ionic liquids and acetonitrile as key solvents. Three iron-catalyzed reactions, the intramolecular cyclization of cyclopropane dithioacetals, the [2+2]-cycloaddition of (trans)-anethole, and the [2+3]-type cycloaddition of styrene derivatives with 1,4-benzoquinone, were first developed using acetonitrile as solvent in the presence of 3 similar to 5 mol% of Fe(ClO4)(3)center dot Al2O3 or Fe(BF4)(2)center dot 6H(2)O under air conditions. In particular, we found the rapid cycloaddition of iron-catalyzed [2+3]-type cycloaddition of styrene derivatives with 1,4-benzoquinone when the reaction was carried out in an ionic liquid which contained [PF6] or [Tf2N] anion. Homo-coupling reaction of aryl or alkynyl Grignard reagent was next discovered using 1 mol% of FeCl3 as catalyst and the reaction also proceeded very rapidly in an ionic liquid. We also found that 3-5 mol% of Fe(ClO4)(2)center dot Al2O3 or Fe(BF4)(2)center dot 6H(2)O-successfully catalyzed Friedel-Crafts type alkylation of indoles or pyrroles with vinyl ketones or alpha-aryl-beta-silylalcohol. In particular, the reaction of chiral alpha-aryl-beta-silylalcohol with indole using Fe(ClO4)(3)center dot nH(2)O as catalyst proceeded with retention of the configuration of stereochemistry of the hydroxyl group. Then, we discovered the first example of iron-catalyzed enantioselective C-S bond formation via Michael addition of thiols to (E)-3-crotonoyloxazolidin-2-one using 10 mol% of Fe(BF4)(2)/Pybox. We further demonstrated that Fe(ClO4)(3)center dot Al2O3-catalyzed the Nazarov type cyclizations of thiophene, pyrrole, indole, benzofuran, and benzo[b]thiophene derivatives using ionic liquids as solvent. Solvents have been recognized as a by-player in chemical reactions in the process of "optimization of reaction conditions". However, further investigation of the solvent-driven iron-catalyzed reaction will allow discovery of useful reactions for organic syntheses.