3,5-dimethylpyrrole-2,4-dicarboxylic acid 2-benzyl ester | 69912-09-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-dimethylpyrrole-2,4-dicarboxylic acid 2-benzyl ester
• 英文别名: 3,5-dimethyl-pyrrole-2,4-dicarboxylic acid 2-benzyl ester；5-(Benzyloxycarbonyl)-2,4-dimethylpyrrol-3-carbonsaeure；Pyrrole-2,4-dicarboxylic acid, 3,5-dimethyl-, 2-benzyl ester；2,4-dimethyl-5-phenylmethoxycarbonyl-1H-pyrrole-3-carboxylic acid
• CAS: 69912-09-0
• 化学式: C₁₅H₁₅NO₄
• 分子量: 273.288
• InChiKey: UKIAVYVRZNDPNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  79.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-dimethylpyrrole-2,4-dicarboxylic acid 2-benzyl ester 在 B2H6-THF 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以80%的产率得到2-((benzyloxy)carbonyl)-3,4,5-trimethylpyrrole
  参考文献：
  名称：

  Pandey, Ravindra K.; Rezzano, Irene N.; Smith, Kevin M., Journal of Chemical Research, Miniprint, 1987, # 8, p. 2171 - 2192

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-二甲基吡咯-2,4-二羧酸2-苄酯4-t-丁酯 在 三氟乙酸 作用下， 以100%的产率得到3,5-dimethylpyrrole-2,4-dicarboxylic acid 2-benzyl ester
  参考文献：
  名称：

  Asymmetric Synthesis of Mono- and Dinuclear Bis(dipyrrinato) Complexes

  摘要：

  The diastereoselective syntheses of Zn(II) bis(dipyrrinato) helicates is reported, involving ligands templated by the incorporation of homochiral binol within the linker joining the two dipyrrinato units. The most diastereoselective formation of dinuclear bis(dipyrrinato) helicates to date is reported. The formation of either mononuclear or dinuclear helicates can be tuned by varying the length of the linker between the dipyrrinato units and by varying the complexation procedure. The neutral dipyrrinato helicates were readily analyzed by HPLC to ascertain diastereoselectivity, and circular dichroism studies revealed the helical nature of the complexes. The molar ellipticities of the helicates produced by diastereoselective complexation are very large in the visible region and typically correspond to binol moieties in the UV region. Extensive X-ray crystallographic investigations further confirmed the helicity of the mononuclear Zn(II) helicates and identified significant interlayer displacement and bending within crystals.

  DOI：

  10.1021/jo070569j

文献信息

• Synthesis and pharmacological characterisation of 2,4-Dicarboxy-pyrroles as selective non-Competitive mGluR1 antagonists
  作者：Fabrizio Micheli、Romano Di Fabio、Paolo Cavanni、Joseph M Rimland、Anna Maria Capelli、Cristiano Chiamulera、Mauro Corsi、Corrado Corti、Daniele Donati、Aldo Feriani、Francesco Ferraguti、Micaela Maffeis、Andrea Missio、Emiliangelo Ratti、Alfredo Paio、Roberta Pachera、Mauro Quartaroli、Angelo Reggiani、Fabio Maria Sabbatini、David G Trist、Annarosa Ugolini、Giovanni Vitulli

  DOI：10.1016/s0968-0896(02)00424-8

  日期：2003.1

  Metabotropic glutamate receptors (mGluRs) are an unusual family of G-protein coupled receptor (GPCR), and are characterised by a large extracellular N-terminal domain that contains the glutamate binding site. We have identified a new class of non-competitive metabotropic glutamate receptor 1 (mGluR1) antagonists, 2,4-dicarboxy-pyrroles which are endowed with nano-molar potency. They interact within the 7 transmembrane (7TM) domain of the receptor and show antinociceptive properties when tested in a number of different animal models. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Li, Guolin; Ma, Qinggago; Ma, Bing, Heterocycles, 1999, vol. 51, # 12, p. 2849 - 2854
  作者：Li, Guolin、Ma, Qinggago、Ma, Bing、Grossman, Zachary D.、Pandey, Ravindra K.

  DOI：——

  日期：——
• Asymmetric Synthesis of Mono- and Dinuclear Bis(dipyrrinato) Complexes
  作者：Adeeb Al-Sheikh Ali、Ronald E. Benson、Sascha Blumentritt、T. Stanley Cameron、Anthony Linden、David Wolstenholme、Alison Thompson

  DOI：10.1021/jo070569j

  日期：2007.6.1

  The diastereoselective syntheses of Zn(II) bis(dipyrrinato) helicates is reported, involving ligands templated by the incorporation of homochiral binol within the linker joining the two dipyrrinato units. The most diastereoselective formation of dinuclear bis(dipyrrinato) helicates to date is reported. The formation of either mononuclear or dinuclear helicates can be tuned by varying the length of the linker between the dipyrrinato units and by varying the complexation procedure. The neutral dipyrrinato helicates were readily analyzed by HPLC to ascertain diastereoselectivity, and circular dichroism studies revealed the helical nature of the complexes. The molar ellipticities of the helicates produced by diastereoselective complexation are very large in the visible region and typically correspond to binol moieties in the UV region. Extensive X-ray crystallographic investigations further confirmed the helicity of the mononuclear Zn(II) helicates and identified significant interlayer displacement and bending within crystals.
• Pandey, Ravindra K.; Rezzano, Irene N.; Smith, Kevin M., Journal of Chemical Research, Miniprint, 1987, # 8, p. 2171 - 2192
  作者：Pandey, Ravindra K.、Rezzano, Irene N.、Smith, Kevin M.

  DOI：——

  日期：——