5-bromo-15-phenyl-10,20-bis(3,5-di-tert-butylphenyl)porphyrin Ni(II) | 545432-83-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-bromo-15-phenyl-10,20-bis(3,5-di-tert-butylphenyl)porphyrin Ni(II)
• 英文别名: C20N4H8(phenyl)(3,5-di-tert-butyl-phenyl)2Br
• CAS: 545432-83-5
• 化学式: C₅₄H₅₅BrN₄Ni
• 分子量: 898.651
• InChiKey: UPKYTYKESMYFNJ-GHJOJRNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
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• 环数：
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• 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：

  5-bromo-15-phenyl-10,20-bis(3,5-di-tert-butylphenyl)porphyrin Ni(II) 、 萘酚 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以91%的产率得到
  参考文献：
  名称：

  Simple and Catalyst-Free Synthesis of meso-O-, -S-, and -C-Substituted Porphyrins

  摘要：

  A simple and efficient method for the meso-functionalization of porphyrin has been developed. Kinetic studies of meso-fluoro-, -chloro-, -bromo-, -iodo-, and -nitro-substituted porphyrins (Ni) with phenol reveal that the reaction undergoes a typical aromatic nucleophilic substitution (SNAr) process. This catalyst-free method can be performed with meso-brominated porphyrins and oxygen-, sulfur-, and carbon-based nucleophiles to achieve a wide variety of meso-substituted porphyrins.

  DOI：

  10.1021/ol500191j
• 作为产物：
  描述：

  溴苯 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 lithium 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 5-bromo-15-phenyl-10,20-bis(3,5-di-tert-butylphenyl)porphyrin Ni(II)
  参考文献：
  名称：

  Simple and Catalyst-Free Synthesis of meso-O-, -S-, and -C-Substituted Porphyrins

  摘要：

  A simple and efficient method for the meso-functionalization of porphyrin has been developed. Kinetic studies of meso-fluoro-, -chloro-, -bromo-, -iodo-, and -nitro-substituted porphyrins (Ni) with phenol reveal that the reaction undergoes a typical aromatic nucleophilic substitution (SNAr) process. This catalyst-free method can be performed with meso-brominated porphyrins and oxygen-, sulfur-, and carbon-based nucleophiles to achieve a wide variety of meso-substituted porphyrins.

  DOI：

  10.1021/ol500191j

文献信息

• Anthracenylporphyrins
  作者：Mia Davis、Mathias O. Senge、Oliver B. Locos

  DOI：10.1515/znb-2010-1211

  日期：2010.12.1

  We report the synthesis and characterization of meso-anthracenylporphyrins with zinc and nickel metal centers. A variety of novel aryl and alkyl meso-substituted anthracenylporphyrins were synthesized via step-wise Suzuki cross-coupling reactions using anthracenyl boronates. This method was compared to standard syntheses based on condensation reactions to yield anthracenylporphyrins of the A2B2- and

  我们报告了具有锌和镍金属中心的中间蒽基卟啉的合成和表征。使用蒽基硼酸酯通过逐步 Suzuki 交叉偶联反应合成了多种新型芳基和烷基内消旋取代的蒽基卟啉。将该方法与基于缩合反应的标准合成方法进行比较，以产生 A 的蒽基卟啉2乙2- 和一个3B型。通过 Suzuki 偶联合成许多功能化的蒽衍生物对该工作进行了补充。对选定的系统进行单晶 X 射线分析，结果显示镍 (II) 蒽基卟啉具有不寻常的紧密堆积。
• Peripherally η¹-Platinated Organometallic Porphyrins as Building Blocks for Multiporphyrin Arrays
  作者：Regan D. Hartnell、Dennis P. Arnold

  DOI：10.1021/om0305869

  日期：2004.2.1

  meso-platinioporphyrin tectons with pyridine, 4,4‘-bipyridine, or various meso-4-pyridylporphyrins in chloroform generate new multicomponent organometallic porphyrin arrays containing up to five porphyrin units. These new types of supramolecular arrays are formed exclusively in high yields and are stable in solution or in the solid state for extended periods. They were characterized by multinuclear NMR and

  外周金属化的变形例内消旋-η 1 -platiniometalloporphyrins，如反式- [PTBR（NiDAPP）（PPH 3）2 ]（H 2 DAPP = 5-苯基10,20双（3' ，5'-二-叔丁基苯基）卟啉），以几乎定量的产率生成类似的硝酸硝基铂（II）和三氟代亲电试剂。这些自组装反应内消旋与吡啶platinioporphyrin tectons，4,4'-联吡啶，或各种内消旋氯仿中的-4-吡啶基卟啉可生成新的多组分有机金属卟啉阵列，其中最多包含五个卟啉单元。这些新型的超分子阵列仅以高收率形成，并且在溶液或固态下可长期稳定。它们的特征在于多核NMR和UV-可见光谱以及高分辨率电喷雾电离质谱。
• Porphyrin Dimer Carbocations with Strong Near Infrared Absorption and Third-Order Optical Nonlinearity
  作者：Karl J. Thorley、Joel M. Hales、Harry L. Anderson、Joseph W. Perry

  DOI：10.1002/anie.200802687

  日期：2008.9.1
• Silylethynyl Substituents as Porphyrin Protecting Groups for Solubilization and Selectivity Control
  作者：Kazuma Oda、Masanari Akita、Satoru Hiroto、Hiroshi Shinokubo

  DOI：10.1021/ol500569b

  日期：2014.3.21

  Silylethynyl substituents are proposed as protecting groups for porphyrin derivatives to enhance their solubility and enable regioselective functionalization. After usage as protecting groups, silylethynyl groups at the mesa-positions can be efficiently removed upon heating with aqueous H2SO4 in the presence of a surfactant. This approach was applied to the preparation of unsymmetrically beta-substituted porphyrins and porphin-porphyrin oligomers, which were inaccessible by conventional methods.