dimethyl 2-ethoxycarbonyl-5-phenyl-pyrrole-3,4-dicarboxylate | 134857-33-3

• 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 2-ethoxycarbonyl-5-phenyl-pyrrole-3,4-dicarboxylate
• 英文别名: 2-O-ethyl 3-O,4-O-dimethyl 5-phenyl-1H-pyrrole-2,3,4-tricarboxylate
• CAS: 134857-33-3
• 化学式: C₁₇H₁₇NO₆
• 分子量: 331.325
• InChiKey: SYTHRYJWCBWIGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  94.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-dimethylamino-4-ethoxycarbonyl-1-thia-3-aza-2-C6H5-butadiene 以 乙醇 、 二氯甲烷 、 硫酸 为溶剂， 生成 dimethyl 2-ethoxycarbonyl-5-phenyl-pyrrole-3,4-dicarboxylate
  参考文献：
  名称：

  Abouelfida, Abdesselam; Pradere, Jean Paul; Jubault, Michel, Canadian Journal of Chemistry, 1992, vol. 70, # 1, p. 14 - 20

  摘要：

  DOI：

文献信息

• Formation of Acyl-Substituted Nitrile Ylides by Rh₂(OAc)₄-Catalyzed Decomposition of<i>α</i>-Diazocarbonyl Compounds in Nitriles
  作者：Kazuaki Fukushima、Toshikazu Ibata

  DOI：10.1246/bcsj.68.3469

  日期：1995.12

  The Rh2(OAc)4-catalyzed reactions of α-diazocarbonyl compounds in nitrile in the presence of dimethyl acetylenedicarboxylate (DMAD) gave oxazole and pyrrole derivatives. The formation of the oxazole derivatives is explained in terms of the 1,5-cyclization of an acyl-substituted nitrile ylide intermediate, and the formation of the pyrrole derivatives is explained by the 1,3-dipolar cycloaddition of

  在乙炔二羧酸二甲酯 (DMAD) 存在下，α-重氮羰基化合物在腈中的 Rh2(OAc)4 催化反应得到恶唑和吡咯衍生物。恶唑衍生物的形成通过酰基取代的腈叶立德中间体的 1,5-环化来解释，吡咯衍生物的形成通过相同中间体与 DMAD 的 1,3-偶极环加成来解释。酰基取代的腈叶立德与丙炔酸甲酯的环加成反应的区域化学表明，丙炔基型共振结构的贡献在酰基取代的腈叶立德反应中起重要作用。
• Formation and Reaction of Acyl Substituted Nitrile Ylide through the Rh₂(OAc)₄-Catalyzed Reaction of α-Diazocarbonyl Compounds with Benzonitrile
  作者：Toshikazu Ibata、Kazuaki Fukushima

  DOI：10.1246/cl.1992.2197

  日期：1992.11

  The rhodium(II) acetate-catalyzed reaction of α-diazocarbonyl compounds with benzonitrile and dimethyl acetylenedicarboxylate gave oxazoles and pyrrole-3,4-dicarboxylates through the 1,5-cyclizatio...

  α-重氮羰基化合物与苯甲腈和乙炔二甲酸二甲酯的乙酸铑（II）催化反应通过 1,5-环化反应得到恶唑和吡咯-3,4-二羧酸酯。
• Application of the Cu(<scp>i</scp>)/TEMPO/O₂ catalytic system for aerobic oxidative dehydrogenative aromatization of pyrrolidines
  作者：Zheng Luo、Yan Liu、Chao Wang、Danjun Fang、Junyu Zhou、Huayou Hu

  DOI：10.1039/c9gc01932d

  日期：——

  A Cu(I)/TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy)-catalyzed aerobic oxidative dehydrogenative aromatization reaction of fully saturated pyrrolidines to synthesize multi-substituted pyrroles was developed for the first time. The use of a non-precious metal catalyst, green oxidant and environmentally friendly solvent made the reaction more sustainable.

  首次开发了Cu（I）/ TEMPO（2,2,6,6-四甲基-1-哌啶基氧基）催化的完全饱和吡咯烷的需氧氧化脱氢芳构化反应，以合成多取代的吡咯。非贵金属催化剂，绿色氧化剂和环保溶剂的使用使反应更加可持续。
• Synthesis of Pyrrole Derivatives Using Thioimidates
  作者：Masataka Yokoyama、Yasuhiro Menjo、He Wei、Hideo Togo

  DOI：10.1246/bcsj.68.2735

  日期：1995.9

  Dimethyl acetylenedicarboxylate, ethyl propiolate, nitro olefins, or 2-nitroalkyl acetates react with thioimidate in the presence of organic bases to give the corresponding pyrroles in moderate-to-good yields.

  二甲基乙炔二羧酸酯、乙基丙烯酸酯、硝基烯烃或2-硝基烷基醋酸酯在有机碱的存在下与硫亚胺反应，生成相应的吡咯，产率中等到良好。
• A selective electrochemical way to functionalized 6H-1,3-thiazines and /or pyrroles.
  作者：Abdesselam Abouelfida、Michel Jubault、Jean-Paul Pradere、Jean-Claude Roze、André Tallec

  DOI：10.1016/s0040-4039(00)79687-0

  日期：1991.5

  4H-1,3-thiazines, easily prepared from 1-thia-3-azabutadienes, appear electroactive in protic medium. Controlled potential electroreductions of 4H-1,-3-thiazines lead either to substituted 6H-1,3-thiazines or to pyrroles according to the nature of the C-4 substituent and the acidity of the supporting electrolyte.