tert – butyl 4 – (cyclopropanecarbonyl)piperazine – 1 – carboxylate (CAS 414910 – 15 – 9) Product Introduction
tert – butyl 4 – (cyclopropanecarbonyl)piperazine – 1 – carboxylate, with the CAS number 414910 – 15 – 9, is a significant organic compound in the field of chemistry. This product has drawn extensive attention due to its unique chemical structure and diverse potential applications. In this comprehensive introduction, we will delve into various aspects of this compound, including its basic properties, wide – ranging uses, applications in different fields, and detailed preparation methods.
I. Chemical Properties
tert – butyl 4 – (cyclopropanecarbonyl)piperazine – 1 – carboxylate has a specific molecular formula and structure. Its molecular formula is \(C_{13}H_{20}N_{2}O_{3}\), and its molecular weight is approximately 252.31 g/mol. The compound contains a piperazine ring, a cyclopropanecarbonyl group, and a tert – butyl carbamate group. The piperazine ring provides a basic heterocyclic structure, which is often involved in hydrogen – bonding and other intermolecular interactions. The cyclopropanecarbonyl group is a relatively small and strained carbonyl – containing group, which can bring special reactivity and steric effects. The tert – butyl carbamate group is a common protecting group in organic synthesis, which can be easily removed under certain conditions.
It is a white to off – white solid at room temperature. Its melting point and boiling point are important physical properties. The melting point of tert – butyl 4 – (cyclopropanecarbonyl)piperazine – 1 – carboxylate is around [specific melting point if available], and its boiling point is approximately [specific boiling point if available]. These values are crucial for its purification and separation processes during synthesis and application. In terms of solubility, it is soluble in some organic solvents such as dichloromethane, chloroform, and ethyl acetate, but has limited solubility in water. This solubility characteristic is related to its hydrophobic and hydrophilic groups. The presence of the tert – butyl group and the cyclopropane ring makes it relatively hydrophobic, while the amide and carbamate groups can form some hydrogen bonds with polar solvents to a certain extent.
II. Uses
1. Intermediate in Organic Synthesis
tert – butyl 4 – (cyclopropanecarbonyl)piperazine – 1 – carboxylate serves as a key intermediate in the synthesis of many complex organic compounds. In the synthesis of pharmaceutical compounds, it can be used to introduce the piperazine – cyclopropanecarbonyl moiety into the target molecule. For example, it can react with various electrophiles or nucleophiles to form new carbon – carbon or carbon – nitrogen bonds. The tert – butyl carbamate group can be removed to expose the free piperazine nitrogen, which can then be further functionalized. This allows for the construction of a variety of bioactive molecules with potential therapeutic applications. In the synthesis of agrochemicals, it can also be used as a building block to introduce specific functional groups, enhancing the biological activity and selectivity of the final products.
2. Ligand in Catalysis
The piperazine and carbonyl groups in tert – butyl 4 – (cyclopropanecarbonyl)piperazine – 1 – carboxylate can coordinate with metal ions, making it a potential ligand in catalytic reactions. It can form stable complexes with transition metals such as palladium, nickel, and copper. These complexes can be used in various catalytic reactions, such as cross – coupling reactions, hydrogenation reactions, and oxidation reactions. The unique structure of the compound can influence the reactivity and selectivity of the catalytic system, leading to more efficient and specific chemical transformations.
III. Applications in Different Fields
1. Pharmaceutical Industry
In the pharmaceutical industry, tert – butyl 4 – (cyclopropanecarbonyl)piperazine – 1 – carboxylate has broad applications. It can be used in the development of drugs for the treatment of various diseases. For example, in the research of central nervous system (CNS) drugs, the piperazine – containing compounds often have good affinity for neurotransmitter receptors. By modifying the structure of tert – butyl 4 – (cyclopropanecarbonyl)piperazine – 1 – carboxylate, new drug candidates with potential antidepressant, antipsychotic, or analgesic activities can be designed. In the field of anti – cancer drug development, the compound can be incorporated into the structure of anti – cancer agents to enhance their targeting ability and cytotoxicity. It can also be used in the synthesis of antibiotics, where the piperazine ring can interact with bacterial cell membranes or enzymes, inhibiting their growth and reproduction.
2. Agrochemical Industry
In the agrochemical industry, this compound can be used to develop pesticides and herbicides. The cyclopropanecarbonyl and piperazine moieties can endow the final products with unique biological activities. For pesticides, they can target specific insect pests, interfering with their nervous systems or metabolic pathways. For herbicides, the compound can be used to design molecules that can inhibit the growth of weeds by affecting their photosynthesis or cell division processes. The use of tert – butyl 4 – (cyclopropanecarbonyl)piperazine – 1 – carboxylate in agrochemical synthesis can improve the effectiveness and environmental friendliness of the products.
3. Material Science
In material science, tert – butyl 4 – (cyclopropanecarbonyl)piperazine – 1 – carboxylate can be used as a monomer or modifier in the synthesis of polymers. The piperazine ring can introduce nitrogen – containing functional groups into the polymer chain, improving its mechanical properties, thermal stability, and solubility. It can also be used to prepare functional materials such as sensors and membranes. For example, by incorporating this compound into a polymer matrix, a sensor material with specific recognition ability for certain analytes can be obtained. The carbonyl and cyclopropane groups can participate in chemical reactions with the analytes, leading to changes in the physical properties of the material, which can be detected and used for sensing purposes.
IV. Preparation Methods
1. One – step Synthesis Method
A possible one – step synthesis method involves the reaction of tert – butyl piperazine – 1 – carboxylate with cyclopropanecarbonyl chloride in the presence of a base. The reaction is usually carried out in an organic solvent such as dichloromethane or tetrahydrofuran. The base, such as triethylamine or pyridine, is used to neutralize the hydrogen chloride generated during the reaction. The reaction equation is as follows: \(C_{9}H_{18}N_{2}O_{2}+C_{4}H_{5}ClO\rightarrow C_{13}H_{20}N_{2}O_{3}+HCl\) The reaction conditions need to be carefully controlled. The temperature is usually maintained at a relatively low level, such as 0 – 5°C, to avoid side reactions. The reaction time can vary from several hours to overnight, depending on the reaction scale and the reactivity of the reagents. After the reaction is completed, the product can be purified by extraction, washing, and column chromatography.
2. Multi – step Synthesis Method
The multi – step synthesis method may start from simpler starting materials. For example, piperazine can be first protected with a tert – butyl carbamate group to form tert – butyl piperazine – 1 – carboxylate. Then, the cyclopropanecarbonyl group can be introduced through a series of reactions. One possible way is to react the protected piperazine with a cyclopropane – containing carboxylic acid derivative under appropriate activation conditions. For instance, the carboxylic acid can be converted to an acid anhydride or an acyl chloride, and then reacted with the piperazine derivative. This multi – step method may require more purification steps between each step, but it can provide better control over the reaction and higher yields in some cases.
V. References
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2. [Reference 2 name]http://example2.com