(2-bromo-5,10,15,20-tetraphenylporphyrinato)nickel(II) | 52588-61-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (2-bromo-5,10,15,20-tetraphenylporphyrinato)nickel(II)
• 英文别名: [2-bromo-5,10,15,20-tetraphenylporphyrinato]nickel(II)；2-bromo-5,10,15,20-tetraphenylporphyrinatonickel(II)；nickel(II)-β-bromotetraphenylporphyrin；Ni(II)-β-bromoTPP；Br(C20H7N4)Ph4Ni
• CAS: 52588-61-1
• 化学式: C₄₄H₂₇BrN₄Ni
• 分子量: 750.319
• InChiKey: HFEUUODVOWRRPL-OWQDCWHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  (2-bromo-5,10,15,20-tetraphenylporphyrinato)nickel(II) 在 (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl 、 potassium tert-butylate 、 palladium diacetate 作用下， 以 甲苯 为溶剂， 反应 63.0h， 以61%的产率得到
  参考文献：
  名称：

  Diporphyrinylamines: Synthesis and Electrochemistry

  摘要：

  The synthesis of three possible diporphyrinylamines is described. All compounds were obtained by using the Buchwald-Hartwig aromatic amination reaction. The electronic spectra of the three porphyrin dimers showed characteristic features found In highly delocalized systems. The first oxidation of these compounds took place on the connecting amine function.

  DOI：

  10.1021/ol2020658
• 作为产物：
  描述：

  tetraphenylporphyrin 在 bis(acetylacetonate)nickel(II) 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 氯苯 为溶剂， 生成 (2-bromo-5,10,15,20-tetraphenylporphyrinato)nickel(II)
  参考文献：
  名称：

  Diporphyrinylamines: Synthesis and Electrochemistry

  摘要：

  The synthesis of three possible diporphyrinylamines is described. All compounds were obtained by using the Buchwald-Hartwig aromatic amination reaction. The electronic spectra of the three porphyrin dimers showed characteristic features found In highly delocalized systems. The first oxidation of these compounds took place on the connecting amine function.

  DOI：

  10.1021/ol2020658

文献信息

• Axially Chiral β,β′-Bisporphyrins: Synthesis and Configurational Stability Tuned by the Central Metals
  作者：Gerhard Bringmann、Daniel C. G. Götz、Tobias A. M. Gulder、Tim H. Gehrke、Torsten Bruhn、Thomas Kupfer、Krzysztof Radacki、Holger Braunschweig、Alexander Heckmann、Christoph Lambert

  DOI：10.1021/ja8055886

  日期：2008.12.31

  is unprecedented. The axial configurations and rotational barriers of the pure atropo-enantiomers were investigated by HPLC-CD experiments on a chiral phase in combination with quantum chemical CD calculations. According to the HPLC experiments and in agreement with quantum chemical calculations by applying the dispersion-corrected BLYP method, the configurational stability of the central porphyrin-porphyrin

  在本文中，通过使用优化的 Suzuki-Miyaura 偶联程序，描述了一种新型的内在手性、直接 β、β' 连接、八-内消旋芳基取代的双卟啉的合成。这种策略导致了各种各样的这种轴向手性“超级双芳基”，它们的金属化状态和取代模式不同。基于通过两步溴化-硼酸化方案制备各种内消旋四芳基卟啉 (TAP) 的未知β-硼酸酯的有效途径，制备了 18 种轴向手性双卟啉衍生物，收率良好至极好。与所有其他直接连接的二聚卟啉系统相比，八个庞大的内消旋取代基和卟啉-卟啉连接的外围位置的联合存在是前所未有的。纯阻转对映体的轴向构型和旋转势垒通过 HPLC-CD 实验结合量子化学 CD 计算在手性相上进行研究。根据 HPLC 实验并与应用色散校正 BLYP 方法的量子化学计算一致，中心卟啉-卟啉轴的构型稳定性强烈依赖于中心金属的性质。环伏安研究证明了内消旋取代基和金属离子对双卟啉氧化电位的系统影响。此处描述的新型轴
• Fluoroalkylation of Porphyrins: A Facile Synthesis of Trifluoromethylated Porphyrins by a Palladium-Catalyzed Cross-Coupling Reaction
  作者：Chao Liu、Qing-Yun Chen

  DOI：10.1002/ejoc.200500027

  日期：2005.9

  Various trifluoromethylated porphyrins can be conveniently synthesized in high yields by the reaction of brominated porphyrins with FSO2CF2COOMe/CuI in the presence of catalytic amounts of Pd2(dba)3·CHCl3/AsPh3. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  在催化量的 Pd2(dba)3·CHCl3/AsPh3 存在下，通过溴化卟啉与 FSO2CF2COOMe/CuI 的反应，可以方便地以高产率合成各种三氟甲基化卟啉。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• General and Efficient Synthesis of <i>meso</i>- and β-Perfluoroalkylated Porphyrins via Pd-Catalyzed Cross-Coupling Reaction
  作者：Qing-Yun Chen、Chao Liu

  DOI：10.1055/s-2005-868484

  日期：——

  A general and efficient method has been developed for the synthesis of meso- and beta-perfluoroalkyl-substituted porphyrins via Pd-catalyzed cross-coupling reaction of meso- and beta-brominated porphyrins with perfluoroalkyl iodides and copper.

  已经开发了一种通用和有效的方法，用于通过 Pd 催化的中间和 β-溴化卟啉与全氟烷基碘化物和铜的交叉偶联反应合成中间和 β-全氟烷基取代的卟啉。
• A new method for the synthesis of porphyrin-α-diones that is applicable to the synthesis of trans-annular extended porphyrin systems
  作者：Maxwell J. Crossley、Paul L. Burn、Steven J. Langford、Simon M. Pyke、Allison G. Stark

  DOI：10.1039/c39910001567

  日期：——

  Porphyrin-α-diones can be prepared by photooxidation or SeO2-oxidation of β-hydroxyporphyrins, which are in turn readily synthesized from the corresponding copper(II) or nickel(II) 2-halo- and 2-sulphinyl-porphyrins by reaction with the anion of E-benzaldoxime; the efficient conversion of the porphyrinoquinoxaline 6 into the diquinoxalino[2,3-g, 2,3-q] porphyrin 9 illustrates the usefulness of the new methodology for the synthesis of trans-annular extended porphyrin systems.

  卟啉-α-二酮可以通过光氧化或SeO2氧化β-羟基卟啉制备，而后者可以通过与E-苯肟阴离子反应，方便地从相应的铜(II)或镍(II) 2-卤素和2-亚磺酰卟啉合成。卟啉喹啉6高效转化为二喹啉[2,3-g, 2,3-q]卟啉9，说明了这种新方法在合成跨环扩展卟啉系统中的实用性。
• Synthesis of porphyrin-steroid conjugates
  作者：Hasrat Ali、Samira Osati、Ehtsham H. Khan、Shafiullah、Johan E. van Lier

  DOI：10.1142/s1088424616501054

  日期：2016.8

  Steroids linked to porphyrin fluorophores are being developed to improve the selectivity of photosensitizers for photodyanamic therapy and fluorescence imaging of steroid-hormone positive cancers. A number of porphyrin derivatives substituted with one or two steroid moieties coupled via a 17[Formula: see text]-ethynyl group of estradiol, testosterone and 19-nortestosterone were synthesized using Pd(II) as a catalyst.

  目前正在开发与卟啉荧光团连接的类固醇，以提高光敏剂的选择性，用于类固醇激素阳性癌症的光动力治疗和荧光成像。我们使用钯（II）作为催化剂，合成了一些通过雌二醇、睾酮和 19-去甲睾酮的 17[式：见正文]-乙炔基团与一个或两个类固醇分子偶联的卟啉衍生物。