4-acetyl-5-methyl-2-phenylpyrrole | 13219-97-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4-acetyl-5-methyl-2-phenylpyrrole
• 英文别名: 1-(2-methyl-5-phenyl-1H-pyrrol-3-yl)ethanone；3-acetyl-2-methyl-5-phenyl-1H-pyrrole；2-methyl-3-acetyl-5-phenylpyrrole；1-(2-methyl-5-phenyl-pyrrol-3-yl)-ethanone；1-(2-Methyl-5-phenyl-pyrrol-3-yl)-aethanon；3-Acetyl-2-methyl-5-phenyl-pyrrol；Ethanone, 1-(2-methyl-5-phenyl-1H-pyrrol-3-YL)-
• CAS: 13219-97-1
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: FGHHOEXZUJMFDD-UHFFFAOYSA-N

物化性质

• 熔点：
  177 °C
• 沸点：
  385.3±30.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-acetyl-5-methyl-2-phenylpyrrole 在 硝酸 、 乙酸酐 作用下， 以70%的产率得到4-acetyl-5-methyl-3-nitro-2-phenylpyrrole
  参考文献：
  名称：

  Almerico, Anna Maria; Cirrincione, Girolamo; Aiello, Enrico, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1631 - 1633

  摘要：

  DOI：
• 作为产物：
  描述：

  4-acetyl-3-amino-5-methyl-2-phenyl-pyrrole 在 盐酸 、 溶剂黄146 、 sodium nitrite 作用下， 以 丙酮 为溶剂， 反应 4.0h， 生成 4-acetyl-5-methyl-2-phenylpyrrole
  参考文献：
  名称：

  Dattolo, Gaetano; Cirrincione, Girolamo; Almerico, Anna Maria, Heterocycles, 1983, vol. 20, # 2, p. 255 - 262

  摘要：

  DOI：

文献信息

• Multicomponent Approach Towards the Synthesis of Substituted Pyrroles under Supramolecular Catalysis Using<i>β</i>-Cyclodextrin as a Catalyst in Water Under Neutral Conditions
  作者：Sabbavarapu Narayana Murthy、Bandaru Madhav、Akkiligunta Vijay Kumar、Kakulapati Rama Rao、Yadavalli Venkata Durga Nageswar

  DOI：10.1002/hlca.200900098

  日期：2009.10

  Synthesis of substituted pyrroles in H2O by using β‐cyclodextrin as a supramolecular catalyst is described. This reaction has several advantages over existing methods and provides substituted pyrroles in good‐to‐excellent yields (79–89%). The supramolecular catalysis of the reaction was studied using 1H‐NMR spectroscopy. β‐Cyclodextrin can be recovered and reused several times without loss of activity

  描述了使用β-环糊精作为超分子催化剂在H 2 O中合成取代的吡咯。与现有方法相比，该反应具有多个优点，并且可以提供高至优异产率（79-89％）的取代吡咯。使用1 H-NMR光谱研究了反应的超分子催化。β-环糊精可以被回收并重复使用多次而不会失去活性。
• Mn(III)-Catalyzed Synthesis of Pyrroles from Vinyl Azides and 1,3-Dicarbonyl Compounds
  作者：Yi-Feng Wang、Kah Kah Toh、Shunsuke Chiba、Koichi Narasaka

  DOI：10.1021/ol802120u

  日期：2008.11.6

  Polysubstituted N-H pyrroles with a wide variety of substituents were prepared from vinyl azides and 1,3-dicarbonyl compounds by using Mn(III) complexes as catalysts.

  通过使用Mn（III）配合物作为催化剂，从叠氮化乙烯基和1,3-二羰基化合物制备具有多种取代基的多取代NH吡咯。
• 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。
• Synthesis of Polysubstituted <i>N</i>-H Pyrroles from Vinyl Azides and 1,3-Dicarbonyl Compounds
  作者：Shunsuke Chiba、Yi-Feng Wang、Guillaume Lapointe、Koichi Narasaka

  DOI：10.1021/ol702727j

  日期：2008.1.1

  pyrrole formation by the reaction of vinyl azides with 1,3-dicarbonyl compounds via the 1,2-addition of 1,3-dicarbonyl compounds to 2H-azirine intermediates generated in situ from vinyl azides; (ii) the Cu(II)-catalyzed synthesis of pyrroles from alpha-ethoxycarbonyl vinyl azides and ethyl acetoacetate through the 1,4-addition reaction of the acetoacetate to the vinyl azides. By applying these two methods

  提出了四和三取代的NH吡咯的两种合成方法：（i）通过将叠氮化物乙烯基与1,3-二羰基化合物通过1,3-二羰基化合物的1,2-加成反应而形成的热吡咯。由叠氮化乙烯原位生成的叠氮中间体; （ii）通过乙酰乙酸酯与乙烯基叠氮化物的1，4-加成反应，由α-乙氧基羰基乙烯基叠氮化物和乙酰乙酸乙酯的Cu（II）催化的吡咯合成。通过应用这两种方法，可以从相同的乙烯基叠氮化物选择性地制备区域异构的吡咯。
• 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。