methyl (Z)-3-phenyl-2-(1H-pyrrole-2-carbonyl)acrylate | 1186419-79-3

• 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 (Z)-3-phenyl-2-(1H-pyrrole-2-carbonyl)acrylate
• 英文别名: methyl 2-benzylidene-3-oxo-3-(1H-pyrrol-2-yl)propanoate；(Z)-methyl 3-phenyl-2-(1H-pyrrole-2-carbonyl)acrylate；methyl (Z)-3-phenyl-2-(1H-pyrrole-2-carbonyl)prop-2-enoate
• CAS: 1186419-79-3
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: CEWKZFHSKFEGQY-BENRWUELSA-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 (Z)-3-phenyl-2-(1H-pyrrole-2-carbonyl)acrylate 在 3ClO₄^(1-)*Fe⁽³⁺⁾*Al₂O₃ 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 1,4,5,6-tetrahydro-6-oxo-5-(3-oxobutyl)-4-phenylcyclopenta[b]pyrrole-5-carboxylate
  参考文献：
  名称：

  Development of Solvent-Driven Iron-Catalyzed Reactions

  摘要：

  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.

  DOI：

  10.3987/rev-16-842
• 作为产物：
  描述：

  2-乙酰基吡咯 在 四氢吡咯 、 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 5.84h， 生成 methyl (Z)-3-phenyl-2-(1H-pyrrole-2-carbonyl)acrylate
  参考文献：
  名称：

  Iodolium salts as halogen-bond donor catalysts in the Nazarov cyclization: the molecular oxygen enigma

  摘要：

  在碘离子催化下，活化前体的Nazarov环化反应可以在氧气存在的情况下实现，以进行催化剂的激活和周转。

  DOI：

  10.1039/d2nj02731c

文献信息

• Iron(III) Salt-Catalyzed Nazarov Cyclization/Michael Addition of Pyrrole Derivatives
  作者：Masamune Fujiwara、Motoi Kawatsura、Shuichi Hayase、Masato Nanjo、Toshiyuki Itoh

  DOI：10.1002/adsc.200800702

  日期：2009.1

  The Nazarov cyclization of two types of pyrrole derivatives was effectively catalyzed by 5 mol% alumina-supported iron(III) perchlorate [Fe(ClO4)3⋅Al2O3 ] which provided the desired cyclization with high trans selectivity in good to excellent yield. The cyclized product was next reacted with a vinyl ketone in the presence of the same iron salt to afford the corresponding Michael product. A sequential

  两种类型的吡咯衍生物的环化纳扎罗夫被有效5摩尔％的氧化铝担载铁（III），高氯酸催化的[Fe（CLO 4）3 ⋅Al 2 ö 3 ]，其提供高的所需的环化反式选择性良好至优异的屈服。然后在相同的铁盐存在下使环化产物与乙烯基酮反应，得到相应的迈克尔产物。吡咯衍生物的Nazarov / Michael顺序反应也已经完成。4,5-二氢环戊[ b ]吡咯-6（1  H）-一衍生物5或5,6-二氢环戊[ b ] pyrrol-4（1  ）的合成途径因此已经使用非常经济的铁催化剂建立了H）一衍生物6。
• Brønsted acid-catalyzed Nazarov cyclization of pyrrole derivatives accelerated by microwave irradiation
  作者：Prabhakar Bachu、Takahiko Akiyama

  DOI：10.1016/j.bmcl.2009.04.109

  日期：2009.7

  The Bronsted acid-catalyzed Nazarov cyclization of pyrrole derivatives was developed. Microwave irradiation accelerated the Nazarov cyclization significantly at 40 degrees C to give cyclopenta[b] pyrrole derivatives in excellent yields with high trans selectivity. (C) 2009 Elsevier Ltd. All rights reserved.