ethyl 4-ethyl-5-formyl-3-methylpyrrole-2-carboxylate | 4391-87-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 4-ethyl-5-formyl-3-methylpyrrole-2-carboxylate
• 英文别名: 4-ethyl-5-formyl-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester；4-Ethyl-5-formyl-3-methyl-2-pyrrolcarbonsaeure-ethylester；5-ethoxycarbonyl-3-ethyl-4-methylpyrrole-2-carboxaldehyde；ethyl 4-ethyl-5-formyl-3-methyl-1H-pyrrole-2-carboxylate；5-formyl(2-ethylformate-3-methyl-4-ethylpyrrole)
• CAS: 4391-87-1
• 化学式: C₁₁H₁₅NO₃
• mdl: MFCD00447433
• 分子量: 209.245
• InChiKey: ZPKWGTHVNZEDTD-UHFFFAOYSA-N

物化性质

• 溶解度：
  0.00 M

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-ethyl-5-formyl-3-methylpyrrole-2-carboxylate 在 溶剂黄146 、 三乙胺 、 肼 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Highly Fluorescent BF₂ Complexes of Hydrazine–Schiff Base Linked Bispyrrole

  摘要：

  A series of BF2 complexes of hydrazine-Schiff base linked bispyrrole have been prepared from a simple two-step reaction from commercially available substances and are highly fluorescent in solution, film, and solid states with larger Stokes shift and excellent photostabilities comparable or even super to those of their BODIPY analogues. These resultant fluorescent dyes are highly susceptible to the postfunctionalization, as demonstrated in this work via the Knoevenagel condensation to introducing functionalities or tether groups to the chromophore.

  DOI：

  10.1021/ol501162f
• 作为产物：
  描述：

  在 ammonium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 0.33h， 生成 ethyl 4-ethyl-5-formyl-3-methylpyrrole-2-carboxylate
  参考文献：
  名称：

  Electrophilic heteroaromatic reactions. 3. The .alpha.-side-chain bromination of some polysubstituted .alpha.-methylpyrroles in the dark. Evidence for the formation of intermediate .sigma. adducts

  摘要：

  DOI：

  10.1021/jo01298a009

文献信息

• Oxidation of pyrrole α-methyl to formyl with ceric ammonium nitrate
  作者：Thomas Thyrann、David A. Lightner

  DOI：10.1016/0040-4039(95)00790-j

  日期：1995.6

  Pyrrole α-aldehydes can be prepared in high yield by oxidation of pyrrole α-methyl groups with ceric ammonium nitrate when the pyrrole ring also has an α-carboxylic acid ester group.

  当吡咯环也具有α-羧酸酯基时，可以通过用硝酸铈铵氧化吡咯α-甲基来高产率地制备吡咯α-醛。
• A New Method for the Synthesis of 1,2-bis(Pyrrol-2-yl)ethenes
  作者：Jianming Cheng、Padmanabhan Sekher、Sukhwindar P. Singh、James E. Gano、Alan R. Morgan

  DOI：10.1080/00397919708003341

  日期：1997.2

  Abstract 1,2-Bis(2-pyrryl)ethenes were synthesized in high yields by the low-valent titanium mediated reductive coupling of pyrrole-2-carboxaldehydes. The reactions of pyrrole-2-carboxaldehyde under lowvalent titanium conditions were different from those of pyrrole-3-carbonyl compounds.

  摘要 通过低价钛介导的吡咯-2-甲醛的还原偶联，以高产率合成了1,2-双(2-吡咯)乙烯。吡咯-2-甲醛在低价钛条件下的反应与吡咯-3-羰基化合物的反应不同。
• A new convergent method for porphyrin synthesis based on a ‘3 + 1’ condensation
  作者：Arezki Boudif、Michel Momenteau

  DOI：10.1039/p19960001235

  日期：——

  porphyrins 30 and 31 including an analogue of the corallistin-A and vic-diacrylic ester porphyrins 32 and 34. For this purpose, synthesis of various tripyrranes and pyrrole-2,5-dicarbaldehydes have been reported and characterized. Studies by dynamic 1H NMR of sterically hindered tripyrranes show conformational exchange, in solution. Structures of the new porphyrins have been confirmed by 1H NMR spectrometry

  基于tripyrranes和吡咯-2,5-二甲醛的“3 + 1”的酸催化缩合的新方法已被使用，在第一次，对于两种类型的卟啉的合成：VIC -dipropionic卟啉酯30和31包括corallistin-A的类似物和VIC -diacrylic卟啉酯32和34为此目的，各种tripyrranes和吡咯-2,5- dicarbaldehydes的合成已有报道和表征。通过空间受阻三吡喃的动态1 H NMR研究显示溶液中的构象交换。新的卟啉的结构已被1证实。1 H NMR光谱法。在邻位引入二丙烯酸酯基团显着影响化合物32和34的电子光谱，它们呈现出氧杂多型吸收模式。
• Dipyrrinone imines: controlling self-association
  作者：Patrick Ward、Rebecca R. Chandler、Michael T. Huggins

  DOI：10.1080/10610278.2013.771777

  日期：2013.5.1

  We report the synthesis of three new dipyrrinone imine analogues and the characterisation of their self-association properties. Based on vapour pressure osmometry and nuclear magnetic resonance studies, placing the imine functional group at C(9) of the dipyrrinone disrupts the native self-association of the dipyrrinone core in a manner that correlates with the conformational A-value of the imine N-substituent

  我们报告了三种新的双吡啉酮亚胺类似物的合成及其自缔合特性的表征。基于蒸汽压渗透压测定法和核磁共振研究，将亚胺官能团置于双吡咯酮的 C(9) 处会以与亚胺 N-的构象 A 值相关的方式破坏双吡喃酮核心的天然自缔合取代基。
• An inexpensive, selective procedure for oxidizing α-methyl to α-formyl pyrroles pavel bobal
  作者：David A. Lightner

  DOI：10.1002/jhet.5570380531

  日期：2001.9

  α-Methylpyrroles are converted to α-formyl by sodium bromate in aqueous methanol in ∼60% yield. Adding 1% ceric ammonium nitrate as a co-oxidant brings the isolated yields of synthetically useful 2-formylpyrroles 2a-d up to ∼70%, or close to those found when using only the considerably more expensive ceric ammonium nitrate as oxidant.

  在含水甲醇中，溴酸钠可将α-甲基吡咯转化为α-甲酰基。加入1％硝酸铈铵作为助氧化剂，可使合成有用的2-甲酰基吡咯2a-d的分离产率提高至约70％，或接近仅使用昂贵得多的硝酸铈铵作为氧化剂时的产率。

表征谱图