4-乙基-3-甲基吡咯-2-甲醛 | 19711-71-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-乙基-3-甲基吡咯-2-甲醛
• 中文别名: 1H-吡咯-2-甲醛,4-乙基-3-甲基-
• 英文名称: 4-ethyl-3-methylpyrrole-2-carboxaldehyde
• 英文别名: 4-Ethyl-3-methyl-2-pyrrolcarbaldehyd；2-formyl-3-methyl-4-ethylpyrrole；2-formyl-4-ethyl-3-methylpyrrole；4-ethyl-2-formyl-3-methylpyrrole；4-ethyl-3-methyl-pyrrole-2-carbaldehyde；4-Aethyl-3-methyl-pyrrol-2-carbaldehyd；4-ethyl-3-methyl-1H-pyrrole-2-carbaldehyde
• CAS: 19711-71-8
• 化学式: C₈H₁₁NO
• mdl: MFCD12923818
• 分子量: 137.181
• InChiKey: UFTLCNDEXXZCGJ-UHFFFAOYSA-N

物化性质

• 熔点：
  84 °C
• 沸点：
  248.1±28.0 °C(Predicted)
• 密度：
  1.067±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-乙基-3-甲基吡咯-2-甲醛 在 乙醇 、 氢溴酸 、 sodium ethanolate 、 一水合肼 作用下， 生成 (4-ethyl-5-bromo-3-methyl-pyrrol-2-yl)-(3-ethyl-4,5-dimethyl-pyrrol-2-ylidene)-methane
  参考文献：
  名称：

  Stress and Depressive Symptoms Among Mexican American Elders

  摘要：

  Although social stressors have successfully predicted depressive symptomatology in a number of populations, few studies have examined the relevance of stressors for Mexican American elders. Results are reported here from a multistage probability sample of 3,050 Mexican Americans aged 65 and older drawn from a 5-state region. Participants reported low levels of education and income, and most reported difficulty in reading or writing in English. Deaths, illness of close other, and financial problems were the three most frequent life events, and many reported financial strains. Depressive symptoms were then regressed on demographic indicators, cognitive status, linguistic acculturation, social supports, and three types of stressors. Being a woman, lower income, decreased income, chronic financial strain, and several health stressors were associated with greater symptomatology. Results identified a cluster of economic stressors and conditions that may play a critical role in the etiology of depressive symptoms in this minority population.

  DOI：

  10.1093/geronb/57.6.p559
• 作为产物：
  描述：

  benzyl 4-ethyl-3-methyl-1H-pyrrole-2-carboxylate 在 氢氧化钾 作用下， 以 水 、 叔丁醇 为溶剂， 反应 15.0h， 以12%的产率得到4-乙基-3-甲基吡咯-2-甲醛
  参考文献：
  名称：

  Novel substituent orientation in Reimer-Tiemann reactions of pyrrole-2-carboxylates

  摘要：

  DOI：

  10.1021/jo00206a012

文献信息

• Regiocontrolled Synthesis of Pyrrole-2-carboxaldehydes and 3-Pyrrolin-2-ones from Pyrrole Weinreb Amides
  作者：Aaron R. Coffin、Michael A. Roussell、Elina Tserlin、Erin T. Pelkey

  DOI：10.1021/jo061043m

  日期：2006.8.1

  A regiocontrolled synthesis of 3,4-disubstituted pyrrole-2-carboxaldehydes was completed in two steps from acyclic starting materials. A Barton−Zard pyrrole synthesis between N-methoxy-N-methyl-2-isocyanoacetamide and α-nitroalkenes or β-nitroacetates provided N-methoxy-N-methyl pyrrole-2-carboxamides (pyrrole Weinreb amides), which were converted into the corresponding pyrrole-2-carboxaldehydes by

  从无环起始原料开始的两步中完成了区域控制的3,4-二取代的吡咯-2-甲醛的合成。N-甲氧基-N-甲基-2-异氰基乙酰胺与α-硝基烯烃或β-硝基乙酸酯之间的Barton-Zard吡咯合成提供了N-甲氧基-N-甲基吡咯-2-羧酰胺（吡咯Weinreb酰胺），将其转化为氢化铝锂处理得到相应的吡咯-2-甲醛。吡咯-2-甲醛的区域选择性氧化得到相应的3，4-二取代的3-吡咯啉-2-酮。
• Synthesis of heteroleptic pyrrolide/bipyridyl complexes of ruthenium(II)
  作者：Travis Lundrigan、Carla L.M. Jackson、Md. Imam Uddin、Lloyd A. Tucker、Adeeb Al-Sheikh Ali、Anthony Linden、T. Stanley Cameron、Alison Thompson

  DOI：10.1139/v2012-045

  日期：2012.8

  The synthesis and characterization of the first heteroleptic pyrrolide/2,2′-bipyridyl complexes of ruthenium(II) are reported. Pyrroles substituted at the 2-position with X = O functionality react with Ru(bipy)₂Cl₂·2H₂O to form complexes in which the pyrrolide ligands chelate to Ru(II). The library of pyrroles includes 2-formyl, 2-keto, 2-carboxylato, 2-sulfinyl, and 2-sulfonyl derivatives.

  报道了第一种钌(II)的杂环吡咯/2,2′-联吡啶配合物的合成和表征。在2-位取代X = O官能团的吡咯与Ru(bipy)₂Cl₂·2H₂O反应，形成吡咯配体与Ru(II)螯合的配合物。吡咯库包括2-醛基、2-酮基、2-羧基、2-砜基和2-磺基衍生物。
• Regioselective substituent effects upon the synthesis of dipyrrins from 2-formyl pyrroles
  作者：Michael H.R. Beh、Carlotta Figliola、Kate-Lyn A.R. Lund、Aleksandra K. Kajetanowicz、Ann E. Johnsen、Elise M. Aronitz、Alison Thompson

  DOI：10.1139/cjc-2017-0662

  日期：2018.7

  The synthesis of symmetric α-free meso-H-dipyrrin hydrobromides from 5-H-2-formyl pyrroles was investigated. The self-condensation produces regioisomeric dipyrrins through adoption of two mechanistic pathways. The key difference between the two pathways lies in which position of the pyrrole directs nucleophilic attack. Through a systematic study involving various substituted and (or) isotopically labelled 5-H-2-formyl pyrroles, we herein provide evidence to suggest that not only do two mechanistic pathways exist, but the steric bulk of the substituent adjacent to the 5-unsubstituted position influences which pathway dominates.

  对5-H-2-甲醛吡咯烷合成对称α-自由meso-H-二吡咯溴化物进行了研究。自缩合通过采用两种机理途径产生位置异构的二吡咯。这两种途径之间的关键区别在于吡咯的哪个位置引导亲核攻击。通过对各种取代和（或）同位素标记的5-H-2-甲醛吡咯进行系统研究，我们提供了证据表明不仅存在两种机理途径，而且邻近5-未取代位置的取代基的立体体积影响哪种途径占主导地位。
• Synthesis of Ring-Fluorinated Porphyrins and Reconstitutional Myoglobins with Their Iron Complexes
  作者：Akihiro Suzuki、Tadashi Tomizawa、Takashi Hayashi、Tadashi Mizutani、Hisanobu Ogoshi

  DOI：10.1246/bcsj.69.2923

  日期：1996.10

  The total syntheses of monofluoroporphyrin derivatives from monofluoropyrroles and the reconstitution of synthetic heme into sperm-whale myoglobin are described. The heme orientation in a cavity of the protein was determined by 1H and 19F NMR studies. It is noted that a fluoro substituent was found to be a useful probe for studying the heme-protein interaction.

  描述了从单氟吡咯类合成单氟卟啉衍生物以及合成血红素重组为抹香鲸肌红蛋白的过程。通过 1H 和 19F NMR 研究确定蛋白质腔中的血红素取向。值得注意的是，发现氟取代基是研究血红素-蛋白质相互作用的有用探针。
• Fischer; Baumann; Riedl, Justus Liebigs Annalen der Chemie, 1929, vol. 475, p. 237
  作者：Fischer、Baumann、Riedl

  DOI：——

  日期：——