2-甲基-5-苯基-1H-吡咯-3-羧酸甲酯 | 28168-20-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2-甲基-5-苯基-1H-吡咯-3-羧酸甲酯
• 英文名称: 2-methyl-5-phenyl-1H-pyrrole-3-carboxylic acid methyl ester
• 英文别名: methyl 2-methyl-5-phenyl-1H-pyrrol-3-carboxylate；2-Methyl-4-phenyl-pyrrol-(4)-carbonsaeure-methylester；3-Carbomethoxy-2-methyl-5-phenylpyrrol；methyl 2-methyl-5-phenyl-1H-pyrrole-3-carboxylate
• CAS: 28168-20-9
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: MUGXIVKPZNPYFB-UHFFFAOYSA-N

物化性质

• 沸点：
  414.2±33.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-乙酰基-4-氧代-4-苯基丁酸甲酯 在 ammonium acetate 、 silica gel 作用下， 反应 0.4h， 以96%的产率得到2-甲基-5-苯基-1H-吡咯-3-羧酸甲酯
  参考文献：
  名称：

  1,4-二酮和乙酸铵的红外热固相合成吡咯

  摘要：

  在硅胶存在下，通过红外辐射辅助的机械化学研磨，可以轻松地用乙酸铵胺化1,4-二酮。减少了浪费，节省了能源。J.杂环化​​学。（2012）。

  DOI：

  10.1002/jhet.744

文献信息

• I 2 –DMSO promoted metal free oxidative cyclization for the synthesis of substituted Indoles and pyrroles
  作者：Addada Ramakrishnam Raju、Regalla Venkata Reddy、Vajja Mallikarjuna Rao、Vema Venkata Naresh、Anna Venkateswara Rao

  DOI：10.1016/j.tetlet.2016.05.025

  日期：2016.6

  A series of di substituted indole and tri substituted pyrrole derivatives were synthesized efficiently by using I2/K2CO3 in DMSO. The novel synthesis method offers the advantage of mild reaction conditions, operational simplicity, higher yields. The method is functional group tolerant and provides quick access to medicinally significant compounds in moderate to high yields.

  通过在DMSO中使用I 2 / K 2 CO 3有效合成了一系列二取代的吲哚和三取代的吡咯衍生物。新颖的合成方法具有反应条件温和，操作简单，产率高的优点。该方法具有官能团耐受性，可以以中等到高产率快速获得具有医学意义的化合物。
• Green multicomponent reaction for synthesis of trisubstituted pyrroles in ionic liquid [bmim]BF4
  作者：G. Narshimha Reddy、Pravin R. Likhar

  DOI：10.1007/s11164-016-2501-3

  日期：2016.9

  5-Trisubstituted pyrrole derivatives were efficiently synthesized by one-pot condensation of 1,3-diones, α-bromoacetophenones, and ammonium acetate in ionic liquid [bmim]BF4. The new synthetic method offers multisubstituted pyrroles with the advantages of mild reaction conditions, operational simplicity, higher yield, and environmental friendliness.

  通过在离子液体[bmim] BF 4中一锅缩合1,3-二酮，α-溴苯乙酮和乙酸铵有效地合成了2,4,5-三取代的吡咯衍生物。新的合成方法提供了多取代的吡咯，具有反应条件温和，操作简便，产率高和环境友好的优点。
• Synthesis of Substituted Pyrroles from N-Vinylic Phosphazenes Derived from β-Amino Acids and α-Bromo Ketones
  作者：Francisco Palacios、Esther Herrán、Gloria Rubiales

  DOI：10.3987/com-02-s(m)36

  日期：——

  Synthesis of di-, tri- and tetrasubstituted pyrroles by reaction of N-vinylic phosphazenes derived from β-amino acids with α-bromo ketones is described.

  描述了通过衍生自 β-氨基酸的 N-乙烯基磷腈与 α-溴酮反应合成二、三和四取代的吡咯。
• Microwave-assisted facile synthesis of trisubstituted pyrrole derivatives
  作者：V. Hanuman Reddy、G. Mallikarjuna Reddy、M. Thirupalu Reddy、Y. V. Rami Reddy

  DOI：10.1007/s11164-015-1966-9

  日期：2015.12

  We report efficient synthesis of pyrrole derivatives by use of microwave irradiation. Quantitative yields were obtained in short reaction times. Low yields of product were obtained from alicyclic amino unsaturated ketone derivatives; higher yields were obtained from aliphatic amino unsaturated ketone derivatives.

  我们报告了利用微波辐照高效合成吡咯衍生物的情况。在很短的反应时间内就获得了定量产率。脂环族氨基不饱和酮衍生物的产率较低；脂肪族氨基不饱和酮衍生物的产率较高。
• Cu(OTf)₂-Catalyzed Synthesis of 2,3-Disubstituted Indoles and 2,4,5-Trisubstituted Pyrroles from α-Diazoketones
  作者：B. V. Subba Reddy、M. Ramana Reddy、Y. Gopal Rao、J. S. Yadav、B. Sridhar

  DOI：10.1021/ol303206w

  日期：2013.2.1

  A novel method has been devised for the synthesis of 2,4,5-trisubstituted pyrrole derivatives through the coupling of alpha-diazoketones with beta-enaminoketones and esters using 10 mol % of Cu(OTf)(2). A wide range of 2,3-disubstituted indole derivatives were also prepared from alpha-diazoketones and 2-aminoaryl or alkyl ketones. The synthetic versatility of this approach has been exemplified In the formal synthesis of homofascaplysin C.