1,2,3-trimethyl pyrrolo<1,2-f>phenanthridine-1,2,3-tricarboxylate | 106479-91-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1,2,3-trimethyl pyrrolo<1,2-f>phenanthridine-1,2,3-tricarboxylate
• 英文别名: Dibenzoindolizin-tricarbonsaeure-(1,2,3)-trimethylester；pyrrolo[1,2-f]phenanthridine-1,2,3-tricarboxylic acid trimethyl ester；Pyrrolo[1,2-f]phenanthridin-1,2,3-tricarbonsaeure-trimethylester
• CAS: 106479-91-8
• 化学式: C₂₂H₁₇NO₆
• 分子量: 391.38
• InChiKey: BHWWSJSDJRPEND-UHFFFAOYSA-N

反应信息

• 作为产物：
  描述：

  4H-Dibenzochinolizin-tetracarbonsaeure-(1,2,3,4)-tetramethylester 在 sodium dichromate 、 溶剂黄146 作用下， 生成 1,2,3-trimethyl pyrrolo<1,2-f>phenanthridine-1,2,3-tricarboxylate
  参考文献：
  名称：

  Diels; Thiele, Journal fur praktische Chemie (Leipzig 1954), 1940, vol. <2> 156, p. 195,200

  摘要：

  DOI：

文献信息

• Phenanthridinium-Based Azomethine Ylides in 1,3-Dipolar Cycloaddition with Dimethyl Acetylenedicarboxylate
  作者：Milan Potáček、Tomáš Topinka、Jiří Dostál、Jaromír Marek

  DOI：10.1135/cccc19942641

  日期：——

  Azomethine ylides generated from 5-(alkoxycarbonylmethyl) phenanthridinium cations I were used in the 1,3-dipolar cycloadditions with dimethyl acetylenedicarboxylate as dipolarophile. The cycloadducts II were found to be very unstable species and readily oxidized to fully aromatic pyrrolo[1,2-f]phenanthridines III. Their structure was compared with the compounds formed by the oxidation of cycloadducts IV of the same ylide with dimethyl fumarate and maleate. In both cases pyrrolines V were found as intermediates. The structure of the products was determined by NMR and MS as well as by X-ray analysis.

  由 5-(烷氧羰基甲基)菲啶鎓阳离子 I 生成的偶氮甲酰亚胺被用于以乙炔二甲酸二甲酯为双极性的 1,3-二极环加成反应。发现环加成产物 II 是非常不稳定的物种，很容易氧化成完全芳香的吡咯并[1,2-f]菲啶 III。我们将它们的结构与同一矢量的环加合物 IV 与富马酸二甲酯和马来酸二甲酯氧化形成的化合物进行了比较。在这两种情况下，都发现了作为中间体的吡咯啉 V。通过核磁共振和质谱以及 X 射线分析确定了产物的结构。