3-ethyl-2-formyl-4-methylpyrrole | 32928-30-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-ethyl-2-formyl-4-methylpyrrole
• 英文别名: 3-ethyl-4-methyl-2-pyrrolecarboxaldehyde；3-ethyl-4-methylpyrrole-2-carboxaldehyde；2-formyl-3-ethyl-4-methylpyrrole；3-ethyl-4-methyl-pyrrole-2-carbaldehyde；3-Aethyl-4-methyl-pyrrol-2-carbaldehyd；1H-Pyrrole-2-carboxaldehyde, 3-ethyl-4-methyl-；3-ethyl-4-methyl-1H-pyrrole-2-carbaldehyde
• CAS: 32928-30-6
• 化学式: C₈H₁₁NO
• mdl: MFCD01365810
• 分子量: 137.181
• InChiKey: HLJTUIXKJNVFGU-UHFFFAOYSA-N

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：

  3-ethyl-2-formyl-4-methylpyrrole 在 氢溴酸 、 溴 、 溶剂黄146 作用下， 生成 (3-ethyl-5-bromo-4-methyl-pyrrol-2-yl)-(4-ethyl-3,5-dimethyl-pyrrol-2-ylidene)-methane; tribromoide
  参考文献：
  名称：

  Siedel; Winkler, Justus Liebigs Annalen der Chemie, 1943, vol. 554, p. 162,185

  摘要：

  DOI：
• 作为产物：
  描述：

  4-ethyl-5-formyl-3-methyl-pyrrole-2-carboxylic acid 在 乙二醇 作用下， 生成 3-ethyl-2-formyl-4-methylpyrrole
  参考文献：
  名称：

  Grigg et al., Justus Liebigs Annalen der Chemie, 1971, vol. 746, p. 32,41,53

  摘要：

  DOI：

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。
• Fast, efficient syntheses of linear poly(dipyrromethene)s
  作者：Qingqi Chen、David Dolphin

  DOI：10.1139/v02-179

  日期：2002.12.1

  The synthesis of three octapyrrolic, 8–10, and four dodecapyrrolic, 15–18, oligomers is reported. They are linear poly(dipyrromethene)s and potential ligands as building blocks for supramolecular architectures through self-assembly. Octapyrrolic oligomers 8–10 were prepared in 90–95% yields by condensation of 2 equiv of a tripyrrolic compound 4 with 1 equiv of diformyldipyrrolic compounds 5–7. A similar procedure, involving the condensation of 2 equiv of a pentapyrrolic starting material 13 with 1 equiv of 5–7 or 14, was found to give rise to the corresponding dodecameric systems 15–18 in 41–56% yields.Key words: poly(dipyrromethene), linear polypyrroles, dipyrromethane, dipyrromethene.

  报道了三种八吡咯烷类（8-10）和四种十二吡咯烷类（15-18）寡聚体的合成。它们是线性聚（二吡咯甲烷）和潜在的配体，可作为超分子结构的构建模块通过自组装。通过将2当量的三吡咯化合物4与1当量的二甲酰二吡咯化合物5-7缩合，制备了八吡咯烷类寡聚体8-10，产率为90-95%。类似的程序涉及将2当量的五吡咯起始物质13与1当量的5-7或14缩合，发现可产生相应的十二聚体系统15-18，产率为41-56%。关键词：聚（二吡咯甲烷），线性聚吡咯，二吡咯甲烷，二吡咯乙烯。
• Studies on the tetramerization of substituted monopyrroles to type I porphyrins
  作者：C Pichon-Santander、A.I Scott

  DOI：10.1016/s0040-4039(02)01592-7

  日期：2002.9

  Investigation of the tetramerization of pyrroles bearing two different electron-donating groups as substituents led to the rapid preparation under slightly acidic conditions of a porphyrin analog family with a high ratio of type I isomer for enzymatic activity studies.

  对带有两个不同的供电子基团作为取代基的吡咯四聚的研究导致在酸性条件下快速制备具有高比例I型异构体的卟啉类似物家族用于酶活性研究。
• Transformation of a monovinylporphyrin to benzoporphyrins via Diels-Alder adducts
  作者：Paul Yon-Hin、Tilak P. Wijesekera、David Dolphin

  DOI：10.1016/s0040-4039(01)93324-6

  日期：——

  β-unsubstituted-β′-vinylporphyrin has been synthesized which reacted with an excess of acetylenedicarboxylate ester to give monobenzoporphyrins in high yield. Evidence that suggests an isomerization of the initial adduct to a new porphyrin enroute to the benzoporphyrin is presented.

  已经合成了β-未取代的-β'-乙烯基卟啉，其与过量的乙炔二羧酸酯反应以高收率得到单苯并卟啉。提出的证据表明初始加合物异构化为新的卟啉，并途经苯并卟啉。
• An efficient route to vinylporphyrins
  作者：Paul Yon-Hin、Tilak Wijesekera、David Dolphin

  DOI：10.1139/v90-289

  日期：1990.10.1

  The use of 1-bromo-19-methylbiladienes-ac in the synthesis of vinylporphyrins is described. The effect of the vinyl precursors on the reactions of the dipyrromethene intermediates and the construction of the linear tetrapyrrole are discussed. High-yield syntheses of a methylvinylporphyrin, an H-vinyl analogue, as well as two A,C-divinylporphyrins are presented. Keywords: pyrrole, dipyrromethene, acetoxyethylpyrrole

  描述了 1-bromo-19-methylbiladienes-ac 在乙烯基卟啉合成中的应用。讨论了乙烯基前体对二吡咯亚甲基中间体反应和线性四吡咯结构的影响。介绍了甲基乙烯基卟啉、H-乙烯基类似物以及两种 A,C-二乙烯基卟啉的高产合成。关键词：吡咯，二吡咯亚甲基，乙酰氧基乙基吡咯，氯乙基吡咯，双二烯-ac，卟啉，乙烯基卟啉，苯并卟啉，脱羧，酯交换。