dimethyl 1,2-diphenyl-1H-pyrrole-3,4-dicarboxylate | 21505-28-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: dimethyl 1,2-diphenyl-1H-pyrrole-3,4-dicarboxylate
• 英文别名: Dimethyl 1,2-diphenyl-1h-pyrrole-3,4-di-carboxylate；dimethyl 1,2-diphenylpyrrole-3,4-dicarboxylate
• CAS: 21505-28-2
• 化学式: C₂₀H₁₇NO₄
• 分子量: 335.359
• InChiKey: JZGIEPZBEMKTAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-N-benzylidenebenzenamine 在 lithium diisopropyl amide 作用下， 以 甲苯 为溶剂， 反应 6.0h， 生成 dimethyl 1,2-diphenyl-1H-pyrrole-3,4-dicarboxylate
  参考文献：
  名称：

  将 α-卤代亚磺酰基碳负离子添加到亚胺中。取代氮丙啶和吡咯的方便制备

  摘要：

  α-锂硫基-α-氯-和-α-氟甲基苯基亚砜与 N-（亚苄基）苯胺反应，以良好的收率得到相应的氮丙啶。在乙炔二羧酸二甲酯存在下这些化合物的热解产生高产率的取代吡咯。

  DOI：

  10.1246/cl.1984.969

文献信息

• An efficient and convenient synthesis of 4-polyfluoroalkylated pyrrole-3-carboxylates through 1,3-dipolar cycloaddition reaction of polyfluoro-2-alkynoic acid esters with munchnones
  作者：Kazumasa Funabiki、Takashi Ishihara、Hiroki Yamanaka

  DOI：10.1016/0022-1139(94)03180-8

  日期：1995.3

  1,3-Dipolar cycloaddition between polyfluoro-2-alkynoic acid esters and 1,3-oxazolium 5-olates (munchnones) readily proceeds in a regiospecific manner under very mild reaction conditions, followed by simultaneous decarboxylation to afford 4-(polyfluoroalkyl)pyrrole-3-carboxylate derivatives in good yield.

  在非常温和的反应条件下，聚氟-2-链烷酸酯和1,3-恶唑鎓5-油酸酯（munchnones）之间的1,3-偶极环加成反应很容易以区域特异性方式进行，然后同时脱羧得到4-（聚氟烷基）吡咯-3-羧酸酯衍生物产率高。
• Catalytic Multicomponent Reactions for the Synthesis of <i>N</i>-Aryl Trisubstituted Pyrroles
  作者：Chris V. Galliford、Karl A. Scheidt

  DOI：10.1021/jo0624086

  日期：2007.3.1

  Dirhodium(II) salts efficiently catalyze the three-component assembly reaction of an imine, diazoacetonitrile (DAN), and an activated alkynyl coupling partner to form substituted 1,2-diarylpyrroles in moderate to good yields. The transition-metal-catalyzed decomposition of the diazo compound in the presence of the imine presumably generates a transient azomethine ylide that undergoes cycloaddition

  铱（II）盐可有效催化亚胺，重氮乙腈（DAN）和活化的炔基偶合伙伴的三组分组装反应，以中等至良好的收率形成取代的1,2-二芳基吡咯。在亚胺的存在下，重氮化合物的过渡金属催化分解可能会产生一种瞬态的甲亚胺叶立德，它以高度收敛的方式与双极性亲和剂进行环加成反应。
• A new method for the synthesis of 2-phenylsulfonylaziridines via the reaction of α-halosulfonyl carbanion to imines
  作者：Vichai Reutrakul、Vichukorn Prapansiri、Chitchanun Panyachotipun

  DOI：10.1016/s0040-4039(01)90084-x

  日期：1984.1

  The reaction of lithio α-chloromethyl phenyl sulfone with imines gave aziridines in good yields. The resulting aziridines were alkylated and underwent the 1,3-dipolar cycloaddition with dimethylacetylene dicarboxylate to give pyrroles in excellent yields.

  硫代α-氯甲基苯基砜与亚胺的反应得到氮丙啶，收率良好。将所得的氮丙啶烷基化，并与二甲基乙炔二羧酸酯进行1，3-偶极环加成反应，以优异的收率得到吡咯。
• The first example of the generation of azomethine ylides from a fluorocarbene: 1,3-cyclization and 1,3-dipolar cycloaddition
  作者：Alexander S. Konev、Mikhail S. Novikov、Alexander F. Khlebnikov

  DOI：10.1016/j.tetlet.2005.09.165

  日期：2005.11

  or dimethyl acetylenedicarboxylate, the products of dehydrofluorination of the primary adducts of the 1,3-dipolar cycloaddition of fluoro-substituted azomethine ylides to multiple bonds of dipolarophiles were obtained. In the case of the reaction of N-alkylimines of benzaldehyde the cycloaddition of ylides to dimethyl maleate completely suppressed the cyclization to aziridines.

  席夫碱与氟碳烯的反应是在超声波辐射下，在Bu 4 NBr存在下，用活性铅将二溴氟甲烷与活性铅还原而生成的，涉及形成氟取代的甲亚胺基化物，将其环化成氮丙啶。由苯甲醛的N-芳基丙氨酸生成的酰基的1，3-环化选择性地进行。当在马来酸二甲酯或乙酰二羧酸二甲酯的存在下使席夫碱与氟碳烯反应时，获得了氟取代的偶氮甲亚胺基的1，3-偶极环加成反应成双极性亲和剂的多个键的伯加氢脱氟化氢的产物。在N反应的情况下-苯甲醛的β-烷基亚胺，酰基化物与马来酸二甲酯的环加成反应完全抑制了环化成氮丙啶的过程。
• Monofluoro-substituted azomethine ylides in fluorocarbene reactions with imines. Synthesis and transformations of monofluoroaziridines
  作者：A. S. Konev、M. S. Novikov、A. F. Khlebnikov

  DOI：10.1134/s1070428007020224

  日期：2007.2

  N-Arylmethylene and N-benzhydrylideneamines react with fluorocarbene yielding fluoro-substituted azomethine ylides that undergo 1,3-pi-cyclization into aziridines. Generation of fluoroylides in the presence of dipolarophiles (dimethyl maleate or dirnethyl acetylenedicarboxylate) led to the reaction of 1,3-dipolar cycloaddition resulting in substituted 2-pyrrolines or pyrroles. 2-Fluoroaziridines, products of N-alkyl-N-benzhydrylideneamines 1,3-pi-cyclization, in the presence of acid catalysts suffer isomerization into alpha-fluoroimines and 1,3-disubstituted indoles.