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What is the chemical structure of 2- (tert-Butoxycarbonylamino) pyridine-4-boronic acid pinacol ester?
2 -% 28tert - Butoxycarbonylamino%29pyridine - 4 - boronic acid pinacol ester, a compound in the field of organic chemistry. According to its naming convention, its chemical structure can be dissected.
"2 - (tert - Butoxycarbonylamino) ", this part indicates that a tert-butoxycarbonyl amino group is connected at position 2 of the pyridine ring. Tert - Butoxycarbonyl (often represented by Boc), as a protective group of amino groups, has specific chemical properties and spatial structure. In its structure, tert-butyl (tert-Butyl) is a group containing three methyl groups connected to the same carbon atom, with a large steric resistance; carbonyl (carbonyl) is a structure connected by a double bond between a carbon atom and an oxygen atom.
"pyridine" is a six-membered nitrogen-containing heterocycle with aromatic properties. The carbon atom and the nitrogen atom on the ring are connected in a special conjugated system, giving the pyridine ring unique chemical activity.
"4-boronic acid pinacol ester" indicates the structure of boronic acid pinacol ester connected at the 4th position of the pyridine ring. Boric acid pinacol ester is an ester formed by boric acid and pinacol (2,3-dimethyl-2,3-butanediol). In the boric acid part, the boron atom is connected to three oxygen atoms, and two oxygen atoms participate in the formation of ester bonds with pinacol. In pinacol, two methyl groups are respectively connected to two adjacent carbon atoms. This structure makes the boric acid pinacol ester have certain stability and reactivity.
In summary, the chemical structure of 2 - (tert - Butoxycarbonylamino) pyridine - 4 - boronic acid pinacol ester is: pyridine ring with tert-butoxycarbonyl amino group at position 2 and boric acid pinacol ester at position 4. The parts are connected to each other to form unique organic compounds, which may have specific uses and reactivity in organic synthesis reactions.
What are the main uses of 2- (tert-Butoxycarbonylamino) pyridine-4-boronic acid pinacol ester?
2-% 28tert - Butoxycarbonylamino%29pyridine - 4 - boronic acid pinacol ester, the Chinese name is often 2 - (tert-butoxycarbonyl amino) pyridine - 4 - boronic acid pinacol ester. This substance has a wide range of uses and is often used as a key intermediate in the field of organic synthesis.
It makes great contributions to pharmaceutical chemistry. The structure of Gainpyridine and borate esters has good biological activity and binding properties. By interacting with specific biological targets, or by participating in the construction of compounds with specific pharmacological activities, it paves the way for the creation of new drugs. When developing anti-cancer drugs, this compound can be used to build a core structure, which can be modified and optimized to enhance the targeting and inhibitory effect of the drug on cancer cells.
In the field of materials science, it also has its uses. Because its structure contains boron elements and specific functional groups, it may endow materials with unique optical and electrical properties. For example, in the preparation of organic optoelectronic materials, the introduction of this compound may be able to regulate the energy level structure of materials and improve their photoelectric conversion efficiency, making it famous in the fields of Light Emitting Diode and solar cells.
Furthermore, in organic synthesis reactions, 2 - (tert-butoxycarbonyl amino) pyridine-4 -boronic acid pinacol esters are often used as coupling reagents. In coupling reactions such as Suzuki-Miyaura, the borate ester part can be coupled with halogenated aromatics or olefins under the action of suitable catalysts and bases to achieve carbon-carbon bond construction, providing an effective path for the synthesis of complex organic molecules, assisting in the construction of organic compounds with diverse structures, and expanding the boundaries of organic synthesis chemistry.
What are the synthesis methods of 2- (tert-Butoxycarbonylamino) pyridine-4-boronic acid pinacol ester?
To prepare 2 - (tert-butoxycarbonyl amino) pyridine-4-boronic acid pinacol ester, there are two common methods.
First, take 2-aminopyridine-4-boronic acid pinacol ester as the starting material, and make it react with tert-butoxycarbonyl anhydride (Boc 2O O) in a suitable solvent and in an alkaline environment. Among them, common solvents such as dichloromethane, tetrahydrofuran, etc., and bases are triethylamine, N, N-diisopropyl ethylamine, etc. During the reaction, the temperature is controlled from low temperature to room temperature for several hours. After the reaction is completed, the target product can be obtained by extraction and column chromatography. The reason for the reaction is that the amino group is acylated with Boc 2O O, and the tert-butoxycarbonyl is attached to the amino group.
Second, with 2 - (tert-butoxycarbonyl amino) pyridine as the starting material, the lithium reaction is first carried out, such as with n-butyl lithium and other reagents in a low temperature, anhydrous and oxygen-free environment, to form a lithium intermediate. Subsequently, a borate ester reagent, such as pinacol borate, is added to heat up the reaction. This process requires strict control of the reaction conditions, and anhydrous and oxygen-free is essential. After the reaction is completed, the pure 2 - (tert-butoxycarbonyl amino) pyridine - 4 - boronic acid pinacol ester can be obtained by regular post-treatment, such as acidification, extraction, drying, column chromatography, etc. In this way, the lithium reaction first activates the pyridine ring, and then reacts with the borate ester to form a carbon-boron bond to obtain the target.
These two methods have their own advantages and disadvantages. The former is simple in steps and easy to control; the latter is rare in raw materials and has harsh reaction conditions, but the yield may be advantageous. In actual synthesis, when considering factors such as raw material availability, cost and product requirements, choose carefully.
What are the physical properties of 2- (tert-Butoxycarbonylamino) pyridine-4-boronic acid pinacol ester?
2-% 28tert - Butoxycarbonylamino%29pyridine - 4 - boronic acid pinacol ester is a compound commonly used in the field of organic synthesis. Its physical properties are worth exploring.
Looking at its morphology, under room temperature and pressure, it is mostly white to white solid. This morphology is easy to store and use, and provides convenience in various synthesis operations.
When it comes to melting point, the melting point of the compound is within a specific range. This melting point property is of great significance for identifying its purity and controlling the synthesis process. Accurate melting point values can help chemists determine whether the substance meets specific standards and can also provide a basis for optimizing reaction conditions.
Solubility is also one of its important physical properties. In common organic solvents, such as dichloromethane, N, N-dimethylformamide, etc., it exhibits good solubility. This property makes it easier to dissolve it in a suitable solvent in an organic synthesis reaction to achieve a homogeneous reaction, improve the reaction efficiency and product yield. However, the solubility in water is relatively poor, due to the dominant position of hydrophobic groups in the molecular structure of the compound.
Furthermore, its stability cannot be ignored. Under normal storage conditions, the compound can remain relatively stable in a dry and cool place. However, it should be noted that it is sensitive to environmental factors such as humidity, temperature and air. When wet, the borate may undergo hydrolysis; high temperature environment may also promote decomposition or other side reactions. Therefore, proper storage and operating conditions are essential to maintain the quality and activity of the compound.
What is the market outlook for 2- (tert-Butoxycarbonylamino) pyridine-4-boronic acid pinacol ester?
2-% 28tert - Butoxycarbonylamino%29pyridine - 4 - boronic acid pinacol ester is an important intermediate in the field of organic synthesis. Looking at its market prospects, it is quite promising for many reasons.
First, in the field of pharmaceutical chemistry, this compound is widely used. Compounds containing boron and pyridine structures have unique advantages in drug development and can be used to construct biologically active molecular structures. In the synthesis path of many new drugs, it is often relied on as a key intermediate to participate in the reaction to prepare substances with specific pharmacological activities. Therefore, with the continuous advancement of pharmaceutical research and development, the demand for it may continue to rise.
Second, in the field of materials science, boron-containing organic compounds are also of concern. 2-% 28tert - Butoxycarbonylamino%29pyridine - 4 - boronic acid pinacol ester can be introduced into polymer materials or functional materials through specific reactions, endowing materials with unique properties such as fluorescence and self-assembly, and is used in optical materials, sensor materials and other fields. With the development of materials science, the demand for materials with special properties will increase, which will also drive the market demand for this compound.
Third, in terms of the development of synthetic chemistry itself, the synthesis methods of organoboron compounds are constantly improving and innovating. The synthesis technology of this compound is also becoming more and more mature, and the cost may be gradually reduced, thereby enhancing its market competitiveness. More scientific research institutions and enterprises may choose this compound as a synthetic raw material due to cost considerations, driving market expansion.
However, its market development also has challenges. The synthesis process may involve complex steps and expensive reagents, and cost control is difficult. And environmental protection requirements are becoming more and more stringent, and the synthesis process needs to conform to the concept of green chemistry, otherwise it may be restricted by the market. But overall, 2% 28tert - Butoxycarbonylamino%29pyridine - 4 - boronic acid pinacol has promising market prospects due to its application potential in many fields. Although there are challenges, there are also opportunities.