5,5'-diformyl-4,4'-dipropyl-2,2'-bipyrrole | 110078-57-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,5'-diformyl-4,4'-dipropyl-2,2'-bipyrrole
• 英文别名: 5,5'-Diformyl-4,4'-di-n-propyl-2,2'-bipyrrol；5-(5-formyl-4-propyl-1H-pyrrol-2-yl)-3-propyl-1H-pyrrole-2-carbaldehyde
• CAS: 110078-57-4
• 化学式: C₁₆H₂₀N₂O₂
• 分子量: 272.347
• InChiKey: RSEWACRPTUFUAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  65.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,5'-diformyl-4,4'-dipropyl-2,2'-bipyrrole 在 吡啶 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以10%的产率得到2,7,12,17-tetra-n-propyl-porphycene
  参考文献：
  名称：

  Vogel, Emanuel; Balci, Metin; Pramod, Kakumanu, Angewandte Chemie, 1987, vol. 99, # 9, p. 909 - 912

  摘要：

  DOI：
• 作为产物：
  描述：

  2-methyl-4-propyl-3,5-dicarbethoxypyrrole 在 sodium hydroxide 、 磺酰氯 、 溴 、 碘 、 sodium acetate 、 铜 、 potassium iodide 、 三氯氧磷 作用下， 以 甲酸 、 乙醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 230.0 ℃ 、26.66 Pa 条件下， 反应 36.0h， 生成 5,5'-diformyl-4,4'-dipropyl-2,2'-bipyrrole
  参考文献：
  名称：

  Vogel, Emanuel; Balci, Metin; Pramod, Kakumanu, Angewandte Chemie, 1987, vol. 99, # 9, p. 909 - 912

  摘要：

  DOI：

文献信息

• Dibenzoporphycene - Platform for the Generation of Fused Porphycenes
  作者：Wolfgang Brenner、Norbert Jux

  DOI：10.1002/ejoc.201403067

  日期：2015.1

  Fused porphycenes have attracted growing interest in recent years. However, the molecules generated to date suffer from different drawbacks such as multistep syntheses, low yields, and the lack of a convenient synthetic strategy. Here, we present our latest results concerning the synthesis of a suitable platform for the generation of large fused porphycenes.

  近年来，稠合卟啉越来越引起人们的兴趣。然而，迄今为止生成的分子存在不同的缺点，例如多步合成、产率低和缺乏方便的合成策略。在这里，我们展示了我们关于合成生成大稠合卟啉的合适平台的最新结果。
• Synthesis and characterization of the new 22-π aromatic furan-containing macrocycle, “ozaphyrin”
  作者：Douglas C. Miller、Martin R. Johnson、John J. Becker、James A. Ibers

  DOI：10.1002/jhet.5570300604

  日期：1993.12

  The new 22-π, aromatic “pentaplanar” macrocycle, ozaphyrin (6), has been synthesized by a McMurry coupling of 5,5′-diformyl-4,4′-dipropyl-2,2′-bipyrrole (1) with 2,5-bis(5-formyl-4-propyl-2-pyrrolyl)furan (5). This synthetic pathway to ozaphyrin and its characterization by 1H nmr spectroscopy, uv-visible spectroscopy, cyclic voltammetry, and X-ray crystallography are described. The structure consists

  新的22-π芳香族“五平面”大环杂卟啉（6）是通过5,5'-二甲酰基-4,4'-二丙基-2,2'-联吡咯（1）与2的McMurry偶联合成的，5-双（5-甲酰基-4-丙基-2-吡咯基）呋喃（5）。描述了该合成的奥扎弗林途径及其通过1 H nmr光谱，紫外-可见光谱，循环伏安法和X射线晶体学表征。该结构由垂直于α轴堆叠的平面交错大环层组成。za杂卟啉在单斜空间群C 5 2h -P2 1 / n中具有四个分子式在尺寸为a = 10.481（7）Å，b = 17.353（17）Å，c = 18.726（12）Å和β= 102.84（5）°（108 K）的像元中。在F 2（5171唯一反射，411个变量）上将结构细化为R w（F o 2）= 0.165。对于3289次反射，当F o 2 > 2 o（F o 2）时，常规一致性指数R（F）为0.074 。
• Highly Fluorescent Bipyrrole‐Based Tetra‐BF ₂ Flag‐Hinge Chromophores: Achieving Multicolor and Circularly Polarized Luminescence
  作者：Luxia Cui、Hyuga Shinjo、Takafumi Ichiki、Koichi Deyama、Takunori Harada、Kohei Ishibashi、Takumi Ehara、Kiyoshi Miyata、Ken Onda、Yoshio Hisaeda、Toshikazu Ono

  DOI：10.1002/anie.202204358

  日期：2022.7.4

  one-pot reaction. The dyes are rigid but can rotate flexibly around the bipyrrole moiety, resulting in large Stokes shifts and high quantum yields. Tuning the rotational barrier enables circularly polarized emission based on axial chirality to be achieved.

  通过一锅反应合成了一系列具有 2,2'-联吡咯配体的四-BF 2配合物，这些配合物在溶液中的可见至红色区域和固态下发光。染料是刚性的，但可以围绕联吡咯部分灵活旋转，从而产生大的斯托克斯位移和高量子产率。调整旋转屏障可以实现基于轴向手性的圆偏振发射。
• 5,15,25-tris-nor-Hexapyrrin: the first structurally characterized linear hexapyrrin
  作者：Jonathan L. Sessler、Steven J. Weghorn、Vincent Lynch、Kjell Fransson

  DOI：10.1039/c39940001289

  日期：——

  The first structurally characterized linear hexapyrrin is prepared with the solid state structure of the dihydrochloric acid salt showing it to lie in a nearly planar S-shaped conformation.

  第一个结构特征为线性的六吡啶以二盐酸盐的固态结构制备，显示其呈近平面的S形构象。
• Photodynamic Antitumor Agents: .beta.-Methoxyethyl Groups Give Access to Functionalized Porphycenes and Enhance Cellular Uptake and Activity
  作者：Clemens Richert、Jurina M. Wessels、Martin Mueller、Michael Kisters、Thomas Benninghaus、Alwin E. Goetz

  DOI：10.1021/jm00043a019

  日期：1994.8

  Porphycene photosensitizers bearing two or four methoxyethyl side chains were synthesized in nine steps from commercially available starting materials. Ether cleavage led to (hydroxyethyl)- and (bromoethyl)porphycenes that were converted to vinyl and benzo derivatives. Five of the side chain-functionalized porphycenes were biologically studied in comparison with two tetra-n-propylporphycenes. Porphycenes were incorporated in small unilamellar liposomes and incubated with cultivated SSK2 murine fibrosarcoma cells. Cellular uptake and phototoxicity 24 h after 5 J/cm(2) laser light treatment were determined. The porphycenes tested were between 17 and 220 times more photodynamically active than the currently clinically used sensitizer Photofrin, although extinction coefficients of the porphycenes' irradiated bands are only approximately 10-fold higher. The LD(50) concentration for SSK2 cells in the incubation medium was as low as (8.5 +/- 2.8) x 10(-9) M for tetrakis(methoxyethyl)porphycene. Two methoxy or hydroxy groups enhanced cellular uptake, three or four methoxy groups both enhanced and accelerated cellular uptake of tetraalkylporphycenes. Half-life times of the uptake processes varied between (0.14 +/- 0.04) and (14 +/- 4) h and cellular saturation levels between (1.2 +/- 0.2) and (26 +/- 3) pmol/10(5) cells. When individual uptake rates were accounted for, all porphycenes had a similar ''cellular'' phototoxicity, pointing toward a common mechanism of action. Evidence is presented for the assumption that cell membranes are the primary targets of the tested porphycenes and that membrane solubility may play a critical role in their photodynamic efficiency. The results show that nonionic polar side chain functionalities can strongly enhance cellular uptake and antitumor activity of lipophilic porphyrinoids and thus that the known lipophilicity/activity relationship can be reversed for very hydrophobic sensitizers.