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Mar. 25th 2025
1-CBZ-2-piperidinecarboxylic acid, also known as N-CBZ-2-piperidinecarboxylic acid, is an important organic compound. CAS: 71170-88-2, molecular formula C14H17NO4, usually a white to almost white powder or crystal. Specific solubility data is not provided, but generally speaking, carboxylic acid compounds are easily soluble in organic solvents such as ethanol, ether, etc., but difficult to dissolve in water. This chemical molecule consists of three parts: a pyridine ring, a carboxyl group, and a benzyloxycarbonyl (Cbz) group.
Among them, the pyridine ring is a six membered ring containing one nitrogen atom; Carboxyl (- COOH) is an acidic functional group; Benzyloxycarbonyl (Cbz) is a commonly used protective group used to protect functional groups such as amino or hydroxyl groups. It is an important precursor for synthesizing multiple medicine. For example, it can be used to synthesize compounds with specific pharmacological activities that play important roles in treating diseases. Through rational medicine design, it can be introduced into medicine molecules, thereby endowing medicines with specific biotic activities.
|
Chemical Formula |
C14H17NO4 |
|
Exact Mass |
263.12 |
|
Molecular Weight |
263.29 |
|
m/z |
263.12 (100.0%), 264.12 (15.1%), 265.12 (1.1%) |
|
Elemental Analysis |
C, 63.87; H, 6.51; N, 5.32; O, 24.31 |
1-CBZ-2-piperidinecarboxylic acid, a unique and functionally diverse organic compound, has demonstrated extensive potential applications in multiple fields.
In the fields of medicine and biotechnology
1. Drug development and production
The product, as an important intermediate in medicine preparation, has been involved in the construction of various medicine molecules. The carboxyl and nitrogen atoms in its structure can react with various functional groups to form substance with specific pharmacological activities. For example, by modifying its structure, medicines with anti-inflammatory, anti-tumor, antibacterial and other activities can be synthesized. These medicines play an important role in clinical medicine, providing effective means for treating various diseases.
2. Preparation of chiral drugs
Chiral medicines have unique advantages in the pharmaceutical field because they can selectively bind to receptors in the body, thereby improving medicine efficacy and reducing side effects. It can be used as a chiral source to prepare medicine molecules with specific chirality. By precise control of its structure, high-purity and highly active chiral medicines can be synthesized to meet the needs of clinical medication.
3. Biological activity research
It itself or its derivatives may have specific biotic activities, such as inhibiting enzyme activity, regulating cell signaling, etc. These biotic activities make them of significant value in medicine screening, target confirmation, and other research. Through in-depth research on its biotic activity, new ideas and directions can be provided for the development of new medicines.
4. Biomedical Engineering
In the field of biomedical engineering, it can also be used as a ligand for material modification to improve the biocompatibility and functionality of biomedical materials. For example, introducing it into biomedical materials can enhance their cell adhesion, anticoagulant properties, and other properties, thereby improving the application effectiveness of biomedical materials.
Pesticides and Agriculture
1. Preparation and modification of pesticides
It also plays an important role in pesticide preparation. By modifying and modifying its structure, pesticide molecules with insecticidal, bactericidal, and herbicidal activities can be synthesized. These pesticide molecules are of great significance in agricultural production, as they can effectively prevent and control pests and diseases, and improve crop yield and quality.
2. Research and development of green pesticides
With the increasing awareness of environmental protection, the research and development of green pesticides has become an important trend in the field of pesticides. The product, as a pesticide intermediate, can be used to synthesize green pesticides with low toxicity, high efficiency, and environmental friendliness. These green pesticides can not only effectively prevent and control pests and diseases in agricultural production, but also reduce pollution and damage to the environment.
Organic synthesis and catalysis field
1. Organic preparation raw materials
The product, as an important organic preparation material, can be used to synthesize various organic substance. These organic substance have wide application value in fields such as chemical industry and materials science. For example, by modifying and modifying its structure, organic polymer materials and organic dyes with specific functions can be synthesized.
2. Catalysts and catalytic reactions
N-CBZ-2-piperidinecarboxylic acid can also serve as a catalyst or precursor for catalysts, playing an important role in chemical reactions. By introducing N-CBZ-2-piperidinecarboxylic acid groups, the rate and selectivity of chemical reactions can be changed, thereby improving the efficiency and yield of chemical reactions. This catalytic effect is of great significance in the chemical industry and can promote the industrialization process of chemical reactions.
Analytical Chemistry and Quality Control Field
1. Chemical analysis standards
N-CBZ-2-piperidinecarboxylic acid can be used as a standard or reference substance for chemical analysis, quality testing, and medicine development. By comparing and analyzing with other substance, the content and structural characteristics of the target substance can be accurately determined, providing reliable data support for chemical analysis and quality testing.
2. Quality control and stability research
N-CBZ-2-piperidinecarboxylic acid can also play an important role in quality control and stability research of medicines, pesticides, and other products. By analyzing and studying its structure, the chemical stability and degradation mechanism of the product can be understood, providing scientific basis for quality control and stability research of the product.
In the field of environmental protection and sustainable development
1. Application of Green Chemistry
N-CBZ-2-piperidinecarboxylic acid has potential application value in the field of green chemistry. By adopting green chemistry technologies and methods, the preparation process can be optimized, reducing pollutant emissions and resource consumption, and achieving sustainable development. For example, green chemistry techniques such as biocatalysis and microwave preparation can be used to synthesize N-CBZ-2-piperidinecarboxylic acid, thereby improving its preparation efficiency and environmental performance.
2. Waste disposal and resource utilization
N-CBZ-2-piperidinecarboxylic acid can also play a certain role in waste disposal and resource utilization. For example, it can be used to treat wastewater or exhaust gases containing organic pollutants, converting them into harmless or reusable substances through chemical reactions. In addition, it can also be used for the resource utilization of waste, reducing resource waste and environmental pollution by recycling and reusing useful components.
The preparation method of 1-CBZ-2-piperidinecarboxylic acid is mainly based on the key raw material of 2-piperidinecarboxylic acid, and the target product is obtained by introducing benzoyl to protect the carboxyl group. Here are some possible preparation paths:
Direct esterification method
This is a common method for synthesizing N-CBZ-2-piperidinecarboxylic acid. The specific steps are as follows:
Firstly, 2-piperidinecarboxylic acid and benzyl chloroformate or benzoyl chloride need to be prepared as reactants. In addition, appropriate solvents (such as dichloromethane, tetrahydrofuran, etc.) and catalysts (such as triethylamine, pyridine, etc.) are also required.
Dissolve 2-piperidinecarboxylic acid in a solvent under inert gas (such as nitrogen) protection and add a catalyst. Then, slowly add benzyl chloroformate or benzoyl chloride dropwise. During the reaction process, it is necessary to control the appropriate temperature and stirring speed to ensure the smooth progress of the reaction.
After the reaction is completed, the catalyst and unreacted raw materials are removed through steps such as filtration, washing, and drying. Next, the product is purified by vacuum distillation or column chromatography to obtain N-CBZ-2-piperidinecarboxylic acid.
Two-step protection method
In addition to direct esterification, a two-step protection method can also be used to synthesize N-CBZ-2-piperidinecarboxylic acid. This method typically involves protection and deprotection steps for carboxyl and amino groups.
Carboxyl protection: Firstly, protect the carboxyl group of 2-piperidinecarboxylic acid, such as introducing methyl or ethyl ester groups through esterification reactions. The purpose of this step is to avoid interference from carboxyl groups during the subsequent amino protection process.
Amino protection: Next, protect the amino group of 2-piperidinecarboxylic acid. This is usually achieved by introducing benzoyl (CBZ) or other protective groups. The protected product can be purified through appropriate post-processing steps.
De protection: After obtaining intermediate products with both amino and carboxyl groups protected, it is necessary to remove the protective groups on the carboxyl groups. This step is usually achieved through reactions such as hydrolysis or acid hydrolysis. After removing the protective group, N-CBZ-2-piperidinecarboxylic acid can be obtained.
Other preparation methods
In addition to the above methods, there may be other pathways for synthesizing N-CBZ-2-piperidinecarboxylic acid. For example, the target product can also be obtained through specific catalytic reactions or rearrangement reactions. However, these methods may need to be adjusted and optimized according to specific reaction conditions and raw materials.
Foundation of Early Protecting Group Technology (1930s)
In 1932, Max Bergmann and Leonidas Zervas first reported the benzyloxycarbonyl (Cbz/Z) protecting group. It realized the controllable protection of amino groups through stable carbamate bonding, pioneering a new approach for peptide preparation.
Featuring acid and alkali resistance as well as removability via catalytic hydrogenation, the Cbz group became a core tool in early peptide chemistry and laid theoretical and methodological foundations for the selective modification of heterocyclic amino acids.
Meanwhile, 2-piperidinecarboxylic acid, a non-proteinogenic amino acid with a cyclic skeleton and chiral center, gained attention in bioactive molecule research, while site-specific N-protection remained undeveloped at that stage.
Structural Derivatization and Early Synthetic Exploration (1950–1980s)
In the 1950s, 2-piperidinecarboxylic acid was systematically isolated from plant and biotic systems, with its metabolic functions and biotic activities gradually clarified.
Researchers introduced the Cbz group via the Schotten-Baumann reaction to address side reactions of secondary amine moieties and racemization of chiral centers in 2-piperidinecarboxylic acid.
This stage was dominated by small-scale laboratory preparation, focusing on verifying the applicability of Cbz protection for heterocyclic amino acids and accumulating basic data for subsequent industrialization.
However, relevant literature was fragmented, and no standardized synthetic procedures were established.
Formal Reporting and Application Expansion (1990s to Present)
In 1993, Journal of Organic Chemistry firstly presented the systematic preparation and characterization of 1-CBZ-2-piperidinecarboxylic acid, establishing the classic route using 2-piperidinecarboxylic acid as raw material and benzyl chloroformate as the acylation reagent, with an overall yield exceeding 96%.
After 2002, with the issuance of patents including US6337423, large-scale industrial production was realized, making this compound a crucial building block for pharmaceutical intermediate manufacturing.
In modern research, its R and S chiral enantiomers are widely applied in the development of enzyme inhibitors, neuroactive medicine and other pharmaceutical molecules.
The Cbz protecting group effectively enhances molecular stability and reaction selectivity, promoting the technological upgrading of heterocyclic medicine preparation.
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