tetrakis-5,10,15,20-(o-aminophenyl)porphyrin | 52199-35-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: tetrakis-5,10,15,20-(o-aminophenyl)porphyrin
• 英文别名: meso(tetra-o-aminophenyl)porphyrin；tetrakis(2-aminophenyl)porphyrin；meso-tetrakis(o-aminophenyl)porphyrin；α,α,α,α-5,10,15,20-tetrakis(2-aminophenyl)porphyrin；5,10,15,20-tetra(2-aminophenyl)porphyrin；α,β,α,β-5,10,15,20-tetra(o-aminophenyl)-21H,23H-porphyrin；α,α,α,α-meso-tetrakis(2-aminophenyl)porphyrin；meso-tetrakis(α,α,α,α-o-aminophenyl)porphyrin
• CAS: 52199-35-6
• 化学式: C₄₄H₃₄N₈
• 分子量: 674.808
• InChiKey: FDJUBNCEVCSIAV-LWQDQPMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.65
• 重原子数：
  52.0
• 可旋转键数：
  4.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  161.44
• 氢给体数：
  6.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  tetrakis-5,10,15,20-(o-aminophenyl)porphyrin 在 氢氧化钾 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 N-(2-[α-10,15,20-tris-(2-acetylamino-phenyl)-porphyrin-α-5-yl]-phenyl)-succinamic acid
  参考文献：
  名称：

  Structural characterisation of the first mononuclear bismuth porphyrin

  摘要：

  一种单羧酸根铋卟啉在固态下首次被表征为非二聚体结构；羧酸根弯曲在大循环上，与铋配位，导致卟啉核心发生显著变形。

  DOI：

  10.1039/b309615g
• 作为产物：
  描述：

  邻硝基苯甲醛 在 盐酸 、 溶剂黄146 、 tin(ll) chloride 作用下， 生成 tetrakis-5,10,15,20-(o-aminophenyl)porphyrin
  参考文献：
  名称：

  Bogatskii, A. V.; Zhilina, Z. I.; Danilina, N. I., Doklady Chemistry, 1980, vol. 251, p. 127 - 129

  摘要：

  DOI：

文献信息

• Catalytic asymmetric epoxidations with chiral iron porphyrins
  作者：John T. Groves、Richard S. Myers

  DOI：10.1021/ja00356a016

  日期：1983.9

  Epoxydation asymetrique d'olefines prochirales par des porphyrines de fer chirales et par des composes iodosyles

  环氧不对称 d'烯烃 prochirales par des porphyrines de fer chirales et par des composes iodosyles
• [EN] SELECTIVE PORPHYRIN-CATALYZED ELECTROCHEMICAL REDUCTION OF CO2 INTO CO, IN PARTICULAR IN WATER<br/>[FR] RÉDUCTION ÉLECTROCHIMIQUE CATALYSÉE DES PORPHYRINES SÉLECTIVES DU CO2 EN CO, PARTICULIÈREMENT DANS L'EAU
  申请人：CENTRE NATIONAL DE LA RECHERCHE SCIENT (CNRS)

  公开号：WO2018011229A1

  公开（公告）日：2018-01-18

  The present invention relates to the use of complexes of water soluble porphyrins of formula (I). The present invention relates to water soluble porphyrins of formula (I), wherein R1 to R11 and R1' to R8' are as defined in claim 1, their iron complexes, use thereof as catalysts for the selective electrochemical reduction of CO2 into CO, electrochemical cells comprising them, and methods for reducing electrochemically CO2 into CO using said complexes or said electrochemical cells, thereby producing CO or syngas.

  本发明涉及使用式(I)的水溶性卟啉的络合物。本发明涉及式(I)的水溶性卟啉，其中R1至R11和R1'至R8'如权利要求1中定义，它们的铁络合物，以及将它们用作CO2选择性电化学还原为CO的催化剂，包括它们的电化学电池，以及使用所述络合物或所述电化学电池将 在电化学上还原为CO的方法，从而产生CO或合成气。
• Histidine Containing Porphyrins Directed for Two Metal Binding Sites
  作者：Masato Ushiyama、Yoji Katayama、Takeshi Yamamura

  DOI：10.1246/cl.1995.395

  日期：1995.5

  Three types of histidine containing porphyrins different in the protection of imidazole N were synthesized by attaching four l-histidyl-glycyl moieties to α,α,α,α-meso-tetra(o-aminophenyl) porphyrin.

  通过将四个L-组氨酰甘氨酸单元附加到α,α,α,α-间四(邻氨基苯基)卟啉上，合成了三种含有组氨酸的不同咪唑氮保护的卟啉。
• A 12-Porphyrin System: Syntheses of Peptide Porphyrins with Multiple Histidines and the Aggregation Behavior in the Presence of Hemin
  作者：Masato Ushiyama、Atsushi Yoshino、Takeshi Yamamura、Yasuo Shida、Fumio Arisaka

  DOI：10.1246/bcsj.72.1351

  日期：1999.6

  We succeeded in combining multiple-histidine peptides with porphyrins; that is to say, we synthesized three peptide porphyrins consisting of α4-meso-tetrakis(o-aminophenyl)porphyrin, α4-H2TAPP, and amphiphilic peptide, α4-(PepA18)n(AG)4−n-H2TAPP (n = 1, 3, and 4; PepA18 = EEALEKHEKALEKHEKAG), in the liquid phase. These compounds were designed to construct multiple porphyrin systems; in other words, each peptide attached on the H2TAPP was designed to contain two histidines. The stability of the porphyrins, (AG)4-H2TAPP and (AG)1(Boc-AG)3-H2TAPP, as well as the coupling conditions between the porphyrin fragments and the 16-residue peptide, EEALEKHEKALEKHEK, to give α4-(PepA18)n(AG)4−n-H2TAPP (n = 1, 3, and 4) were studied in detail with respect to the temperature, solvents, coupling reagents, additives, and amines. This search revealed that the combination of DMF/benzotriazol-1-yl-oxy-tris(pyrrolidino)phosphonium hexafluorophosphate (PyBOP)/N,N-diisopropylethylamine is suitable for the purpose. The search also clarified that it is possible to synthesize α4-(PepA18)4-H2TAPP and α4-(PepA18)3(AG)1-H2TAPP selectively by choosing the coupling additives 1-hydroxy-7-azabenzotriazole (HOAt) and 1-hydroxybenzotriazole (HOBt), respectively.All of the compounds showed 40% helicity in a solution (phospate buffer, pH = 7.0) containing 2,2,2-trifluoroethanol (TFE). The UV-vis and circular-dichroism spectrophotometric titrations of Fe(III) protoporphyrin IX chloride, B, with α4-(PepA18)4-ZnTAPP, A, indicated that up to three equivalents of B were incorporated into A in a buffer solution containing 15% TFE. Sedimentation-equilibrium ultracentrifugation experiments showed that A is a dimer in the solution, and that this dimer is transformed to a trimer when B is incorporated into A. These results suggest that A achieves a 12-porphyrin system consisting of different kinds of metalloporphyrin.

  我们成功地将多组氨酸肽与卟啉结合，即在液相中合成了三种由α4-均四(邻氨基苯基)卟啉、α4-H2TAPP和两亲性肽组成的肽卟啉，α4-(PepA18)n(AG)4−n-H2TAPP（n=1,3,4；PepA18=EEALEKHEKALEKHEKAG）。这些化合物旨在构建多卟啉体系；换言之，每个附着在H2TAPP上的肽段设计为含有两个组氨酸。针对温度、溶剂、偶联试剂、添加剂和胺，详细研究了卟啉的稳定性，(AG)4-H2TAPP和(AG)1(Boc-AG)3-H2TAPP，以及卟啉片段与16残基肽，EEALEKHEKALEKHEK之间的耦合条件，以生成α4-(PepA18)n(AG)4−n-H2TAPP（n=1,3,4）。研究发现，DMF/苯并三唑-1-基氧基三(吡咯烷基)磷鎓六氟磷酸盐(PyBOP)/N,N-二异丙基乙胺的组合适用于此目的。研究还阐明，通过选择偶联添加剂1-羟基-7-氮杂苯并三唑(HOAt)和1-羟基苯并三唑(HOBt)，可以有选择性地合成α4-(PepA18)4-H2TAPP和α4-(PepA18)3(AG)1-H2TAPP。所有化合物在含有2,2,2-三氟乙醇(TFE)的溶液(磷酸盐缓冲液，pH=7.0)中均显示出40%的螺旋度。Fe(III)原卟啉IX氯化物B与α4-(PepA18)4-ZnTAPP，A的紫外-可见光和圆二色光谱滴定表明，在含有15% TFE的缓冲溶液中，最多可掺入三个当量的B到A中。沉降平衡超速离心实验显示，A在溶液中为二聚体，当B掺入A时，该二聚体转变为三聚体。这些结果表明，A实现了由不同金属卟啉组成的12卟啉体系。
• Chiral basket-handle porphyrin-Co complexes for the catalyzed asymmetric cycloaddition of CO 2 to epoxides
  作者：Xiying Fu、Xinyao Jing、Lili Jin、Lilong Zhang、Xiaofeng Zhang、Bin Hu、Huanwang Jing

  DOI：10.1016/s1872-2067(18)63023-2

  日期：2018.5

  which have different chirality, and then applied to the coupling of propylene oxide and CO2 for generating chiral cyclic carbonates with good enantioselectivity under extremely mild conditions in the presence of tetrabutyl ammonium chloride as a co-catalyst. The good enantioselectivity in the cycloaddition reaction is attributed to a synergistic interplay between the chiral porphyrin catalysts and the

  摘要 通过将 CO2 环加成到环氧化物催化合成环状碳酸酯是固定 的标准方法。为此，设计、制备了手性篮柄卟啉-钴配合物，并通过核磁共振、质谱、傅里叶变换红外光谱、紫外-可见光谱和比旋光度对其进行了充分表征。所提出的金属卟啉催化剂是用具有不同手性的 1,1'-双-2-萘酚或 L-苯丙氨酸合成的，然后应用于环氧丙烷和 的偶联，以在极其温和的条件下生成具有良好对映选择性的手性环状碳酸酯。在四丁基氯化铵作为助催化剂存在的条件下。环加成反应中良好的对映选择性归因于手性卟啉催化剂和底物之间的协同相互作用。讨论了不对称环加成反应的机理和对映选择性。

表征谱图