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What is the chemical structure of 1- (phenylsulfonyl) -4-bromo-2-iodo-7-azaindole?
The chemical structure of 1- (benzenesulfonyl) -4-bromo-2-iodine-7-azaiindole is an important topic in the field of organic chemistry. Looking at the name of this compound, its structure can be analyzed according to the picture.
"7-azaiindole", this is the core parent nucleus, that is, the nitrogen atom in the indole structure replaces the carbon atom at the fusion of the benzene ring and the pyrrole ring, forming a unique nitrogen-containing heterocyclic structure. " 1- (benzenesulfonyl) ", it is stated that benzenesulfonyl (-SO 2O Ph) is connected to the first position of the 7-azaindole parent nucleus, and benzenesulfonyl is formed by the connection of the benzene ring and the sulfonyl group (-SO 2O -), which endows the molecule with specific electronic effects and steric resistance." 4-Bromine "and" 2-iodine "refer to the bromine atom and the iodine atom occupying the 4th and 2nd positions of the 7-azaindole parent nucleus, respectively. Both bromine and iodine are halogen elements, and their introduction changes the reactivity and physical properties of the molecule.
In summary, the chemical structure of 1- (benzenesulfonyl) -4-bromo-2-iodine-7-azaindole is composed of 7-azaindole parent nucleus as the group, 1-position benzenesulfonyl, and the 2nd and 4th positions are respectively connected to iodine atoms and bromine atoms. Such a unique structure must endow the compound with specific chemical and physical properties, which may have potential application value in organic synthesis, pharmaceutical chemistry and other fields.
What are the main synthesis methods of 1- (phenylsulfonyl) -4-bromo-2-iodo-7-azaindole?
The synthesis of 1- (phenylsulfonyl) -4-bromo-2-iodine-7-azaiindole has always been an important topic in organic synthetic chemistry. The main synthesis methods include the following.
First, 7-azaiindole is used as the starting material. The first position of 7-azaiindole is phenylsulfonylated. This step can be obtained by reacting 7-azaiindole with phenylsulfonyl chloride in the presence of a suitable base. Bases such as potassium carbonate and sodium carbonate are heated and stirred in a suitable organic solvent such as N, N-dimethylformamide (DMF) to obtain 1- (phenylsulfonyl) -7-azaiindole. Then, the halogenation reaction is carried out. A brominating agent such as N-bromosuccinimide (NBS), in the presence of an initiator such as benzoyl peroxide, in a solvent such as carbon tetrachloride, can be introduced into the bromine atom at the 4 position by light or heat to obtain 1- (phenylsulfonyl) -4-bromo-7-azaindole. Finally, an iodizing agent such as potassium iodide can be introduced into the iodine atom at the 2 position under the action of an oxidizing agent such as hydrogen peroxide or potassium persulfate. 1- (phenylsulfonyl) -4-bromo-2-iodine-7-azaindole.
Second, starting from the construction of nitrogen-containing heterocycles. Using suitable substituted pyridine derivatives as raw materials, a 7-azaiindole skeleton was constructed through multi-step reaction, and phenylsulfonyl, bromine and iodine atoms were introduced at the same time. If the nucleophilic substitution reaction is carried out first, a suitable substituent is introduced at a specific position of the pyridine ring, and the substituent can be formed by subsequent cyclization reaction. Before and after cyclization, phenylsulfonylation, bromination and iodization reactions are carried out in sequence, and the target product can also be obtained. The reaction conditions need to be carefully regulated, and factors such as solvent, base and reaction temperature have a significant impact on the reaction process and product yield.
Third, the synthesis strategy of transition metal catalysis is adopted. Using transition metals such as palladium and copper as catalysts, the coupling reaction between halogenated aromatics and nitrogen-containing heterocyclic compounds is utilized. For example, the coupling reaction between aromatic hydrocarbon derivatives containing iodine and bromine and 7-azaiindole derivatives is carried out under basic conditions in the presence of palladium catalysts and suitable ligands, and phenyl sulfonyl, bromine and iodine atoms can be introduced at the same time. This method requires the selection of suitable catalysts and ligands to improve the selectivity and efficiency of the reaction. The solvent is usually toluene, dioxane, etc., and bases such as potassium tert-butyl alcohol to achieve efficient synthesis of 1- (phenylsulfonyl) -4-bromo-2-iodine-7-azaiindole.
In what fields is 1- (phenylsulfonyl) -4-bromo-2-iodo-7-azaindole used?
1 - (benzenesulfonyl) -4-bromo-2-iodine-7-azaindole is useful in many fields such as medicine and materials science.
In the field of medicine, its effect is significant. Due to its unique structure, it has the potential to interact with bioactive molecules. It can be used as a lead compound for pharmaceutical chemists to modify and optimize to develop new drugs. For example, it may be able to target specific disease-related targets, such as abnormal protein targets involved in some cancers, and modify the structure of the compound to enhance its affinity and selectivity with the target, so as to develop anti-cancer drugs with good efficacy.
In the field of materials science, it also has important applications. It can be used as a functional material building unit. Because it contains halogen atoms such as bromine and iodine and azaiindole structure, it may endow the material with special photoelectric properties. For example, in organic Light Emitting Diode (OLED) materials, its unique structure may optimize the luminous efficiency and stability of the material, so that the luminous performance of OLED devices can be improved. Or it can be used to prepare organic photovoltaic materials. By adjusting the molecular structure, the material can improve the light absorption and charge transport ability of the material, and improve the photoelectric conversion efficiency of photovoltaic devices.
In addition, in the field of chemical synthesis, this compound, as a key intermediate, can participate in a variety of chemical reactions, and through various reaction pathways, it can be derived from compounds with rich and diverse structures, providing more possibilities and options for organic synthesis chemistry, enabling scientists to create novel organic molecules with specific functions.
What are the physical properties of 1- (phenylsulfonyl) -4-bromo-2-iodo-7-azaindole?
1 - (benzenesulfonyl) -4-bromo-2-iodine-7-azaindole, this is an organic compound with specific physical properties. Its appearance is often solid, or powder or crystalline. Due to intermolecular forces, such as van der Waals force and hydrogen bonding, the molecules are arranged in an orderly manner. Its color may be white to light yellow, and factors such as purity and crystal form can cause color differences.
Melting point is also an important physical property. However, there is no universal exact value for the melting point of this compound, which is affected by purity, crystal form and determination method. In general, the melting point range of organic solid compounds is narrow, and this compound may have a clear melting point, which can be accurately determined by experiments.
Solubility is also critical. Its solubility may be good in organic solvents, such as common dichloromethane, chloroform, N, N-dimethylformamide (DMF), etc. In dichloromethane, it can achieve good solubility due to the principle that the molecular structure is similar to that of dichloromethane. However, its solubility in water is poor, because its molecule contains hydrophobic benzene rings and complex heterogeneous ring structures, and its ability to form hydrogen bonds with water is weak.
In addition, the compound has certain stability, but it reacts under specific conditions, such as high temperature, strong acid and alkali environment, or due to active functional groups such as bromine and iodine in the molecule. For example, under the conditions of nucleophilic substitution, bromine and iodine atoms may be replaced by other nucleophilic reagents.
What are the chemical properties of 1- (phenylsulfonyl) -4-bromo-2-iodo-7-azaindole?
1 - (benzenesulfonyl) -4-bromo-2-iodine-7-azaindole, an organic compound. Its chemical properties are unique and related to the field of organic synthesis and medicinal chemistry.
First, the presence of halogen atoms, namely 4-bromine and 2-iodine, endows the compound with active reactivity. Both bromine and iodine atoms are good leaving groups and can participate in nucleophilic substitution reactions. For example, under appropriate nucleophilic reagents and reaction conditions, bromine or iodine atoms can be replaced by other functional groups, such as hydroxyl groups, amino groups, etc., to form new carbon-heteroatomic bonds for the synthesis of more complex organic molecules.
Furthermore, benzenesulfonyl also affects its chemical properties. Benzenesulfonyl has electron-absorbing properties, which can reduce the electron cloud density on the indole ring, making the indole ring more prone to electrophilic substitution reaction, and will affect the selectivity of the reaction check point. At the same time, benzenesulfonyl is relatively stable, and can be used as a protective group to protect a specific position on the indole ring under some reaction conditions. The protective group is removed at a suitable time for subsequent reactions.
In addition, the nitrogen atom in the 7-azaiindole structure changes the electron distribution of the indole ring, and its reactivity and selectivity are different from those of ordinary indoles. This nitrogen atom can be used as a potential coordination atom to form complexes with metal ions, and then participate in metal-catalyzed organic reactions, expanding the application range of this compound in organic synthesis.
In short, 1- (benzenesulfonyl) -4-bromo-2-iodine-7-azaiindole contains halogen atoms, benzenesulfonyl groups and 7-azaiindole structures, which exhibit rich chemical properties and have important research and application value in the field of organic synthetic chemistry.