2,4-dicarbethoxy-3-propylpyrrole-5-carbaldehyde | 142038-33-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2,4-dicarbethoxy-3-propylpyrrole-5-carbaldehyde
• 英文别名: diethyl 5-formyl-3-propyl-2,4-pyrroledicarboxylate；5-formyl-3-propyl-pyrrole-2,4-dicarboxylic acid diethyl ester；5-Formyl-3-propyl-pyrrol-2,4-dicarbonsaeure-diaethylester；Diethyl 5-formyl-3-propyl-1H-pyrrole-2,4-dicarboxylate
• CAS: 142038-33-3
• 化学式: C₁₄H₁₉NO₅
• 分子量: 281.309
• InChiKey: RUJFOGCOHQYSKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4-dicarbethoxy-3-propylpyrrole-5-carbaldehyde 在 劳森试剂 、 sodium hydroxide 、 3,4-二甲基-5-(2-羟乙基)碘代噻唑 、 三乙胺 作用下， 以 1,4-二氧六环 、 乙醇 、 水 、 甲苯 为溶剂， 68.0~240.0 ℃ 、13.33 Pa 条件下， 反应 48.0h， 生成 2,5-bis(4-propyl-2-pyrrolyl)thiophene
  参考文献：
  名称：

  Synthesis and characterization of a new 26.pi.-aromatic thiophene-containing macrocyclic ligand

  摘要：

  A new porphyrin-like or ''pentaplanar'' macrocyclic ligand (9) has been synthesized by a McMurray coupling of 2,5-bis(5-formyl-4-propyl-2-pyrrolyl)thiophene, followed by air oxidation in chloroform. This highly stable macrocycle is aromatic, as evidenced by its UV-visible and H-1 NMR spectra. The pathway to 9 as well as the synthesis of two asymmetric dipyrrolylthiophenes is also described.

  DOI：

  10.1021/jo00042a019
• 作为产物：
  描述：

  2-methyl-4-propyl-3,5-dicarbethoxypyrrole 在 磺酰氯 、 溶剂黄146 作用下， 反应 0.5h， 以67%的产率得到2,4-dicarbethoxy-3-propylpyrrole-5-carbaldehyde
  参考文献：
  名称：

  Synthesis and characterization of a new 26.pi.-aromatic thiophene-containing macrocyclic ligand

  摘要：

  A new porphyrin-like or ''pentaplanar'' macrocyclic ligand (9) has been synthesized by a McMurray coupling of 2,5-bis(5-formyl-4-propyl-2-pyrrolyl)thiophene, followed by air oxidation in chloroform. This highly stable macrocycle is aromatic, as evidenced by its UV-visible and H-1 NMR spectra. The pathway to 9 as well as the synthesis of two asymmetric dipyrrolylthiophenes is also described.

  DOI：

  10.1021/jo00042a019

文献信息

• 3,6,13,16-Tetrapropylporphycene: Rational Synthesis, Complexation, and Halogenation
  作者：Jodukathula Nagamaiah、Arnab Dutta、Narendra Nath Pati、Sameeta Sahoo、Rahul Soman、Pradeepta K. Panda

  DOI：10.1021/acs.joc.1c02652

  日期：2022.3.4

  time as its alkyl analogue from ethyl 4-propyl-1H-pyrrole-2-carboxylate. The substituent effect was found to be more intense than reported positional isomeric tetrapropylporphycenes. The freebase porphycene exhibited moderate fluorescence and complexation ability with divalent metal ions, including Zn(II), which displayed an enhanced emission quantum yield (∼30%). The Pd(II) complex and freebase β-tetrabromoporphycene

  我们首次以4-丙基-1 H-吡咯-2-甲酸乙酯为原料设计合成了3,6,13,16-四丙基卟啉作为其烷基类似物。发现取代基效应比报道的位置异构四丙基卟啉更强烈。游离碱卟啉表现出中等的荧光和与包括 Zn(II) 在内的二价金属离子的络合能力，表现出增强的发射量子产率 (~30%)。Pd(II) 配合物和游离碱 β-四溴卟啉有效地产生单线态氧（分别为 75% 和 51%），因此可能会在光动力治疗中作为潜在的光敏剂应用。
• Vinylpyrroles: solid-state structures and aggregation-induced emission properties
  作者：Toru Okawara、Yurina Matsufuji、Kouhei Mizuno、Kenji Takehara、Toshihiko Nagamura、Seiji Iwasa

  DOI：10.1039/c9ra04088a

  日期：——

  vinylpyrrole, was prepared from a formylpyrrole derivative, Meldrum's acid, and 1,3-dimethylbarbituric acid. The optical properties of the chromophore both in the solution and solid states were investigated by UV-vis and fluorescence spectroscopy. Single crystal X-ray diffraction measurements revealed that the dimethylbarbituric acid adduct formed a J-aggregate in the solid and resulted in higher fluorescence

  由甲酰基吡咯衍生物、Meldrum 酸和 1,3-二甲基巴比妥酸制备聚集诱导的发射发色团乙烯基吡咯。通过紫外-可见光谱和荧光光谱研究了溶液和固态生色团的光学性质。单晶 X 射线衍射测量表明，与 Meldrum 的酸加合物相比，二甲基巴比妥酸加合物在固体中形成 J-聚集体并产生更高的荧光量子产率。发现发射增强是通过限制固态中的分子旋转而发生的。
• JP2016/160239
  申请人：——

  公开号：——

  公开（公告）日：——
• Fischer; Goldschmidt; Nuessler, Justus Liebigs Annalen der Chemie, 1931, vol. 486, p. 33
  作者：Fischer、Goldschmidt、Nuessler

  DOI：——

  日期：——
• Synthesis and characterization of a new 26.pi.-aromatic thiophene-containing macrocyclic ligand
  作者：Martin R. Johnson、Douglas C. Miller、Kristine Bush、John J. Becker、James A. Ibers

  DOI：10.1021/jo00042a019

  日期：1992.7

  A new porphyrin-like or ''pentaplanar'' macrocyclic ligand (9) has been synthesized by a McMurray coupling of 2,5-bis(5-formyl-4-propyl-2-pyrrolyl)thiophene, followed by air oxidation in chloroform. This highly stable macrocycle is aromatic, as evidenced by its UV-visible and H-1 NMR spectra. The pathway to 9 as well as the synthesis of two asymmetric dipyrrolylthiophenes is also described.