Production Method 1

832114-06-4

864754-07-4

Reaction Conditions

1.1 Reagents: Nitromethane ,  Oxygen Catalysts: Iridium(1+), [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-κN1,κN1′]bis[3,5-diflu… Solvents: Methanol ;  2 h, rt

Reference

Mild and Functional Group-Tolerant Aerobic N-Dealkylation of Tertiary Amines Promoted by Photoredox Catalysis

Yilmaz, Ozgur ; et al, Journal of Organic Chemistry, 2023, 88(13), 8874-8881

1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]piperazine Raw materials

• 4-(4-Methylpiperazine-1-carbonyl)phenylboronic Acid Pinacol Ester

1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]piperazine Preparation Products

• 1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]piperazine (864754-07-4)

• 1. An artificial photosynthesis system comprising a covalent triazine framework as an electron relay facilitator for photochemical carbon dioxide reduction?
  Siquan Zhang,Shengyao Wang,Liping Guo,Hao Chen,Bien Tan,Shangbin Jin J. Mater. Chem. C, 2020,8, 192-200
• 2. An atomically efficient, highly stable and redox active Ce0.5Tb0.5Ox (3% mol.)/MgO catalyst for total oxidation of methane?
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• 3. An investigation into the origin of variations in photovoltaic performance using D–D–π–A and D–A–π–A triphenylimidazole dyes with a copper electrolyte?
  Govind Reddy Mol. Syst. Des. Eng., 2021,6, 779-789
• 4. An antimonate pyrochlore (H1.23Sr0.45SbO3.48) for photocatalytic oxidation of benzene: effective oxygen usage and excellent activity?
  Jing Chen,Yu Shao,Danzhen Li J. Mater. Chem. A, 2017,5, 937-941
• 5. An amplified fluorescence detection of T4 polynucleotide kinase activity based on coupled exonuclease III reaction and a graphene oxide platform?
  Ni-Na Sun,Fengli Qu,Xiaobing Zhang,Shufang Zhang,Jinmao You Analyst, 2015,140, 1827-1831

• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzamides
• Solvents and Organic Chemicals Organic Compounds Benzenoids Benzene and substituted derivatives Benzoic acids and derivatives Benzamides

Introduction to 1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]piperazine and Its Significance in Modern Chemical Research

1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]piperazine (CAS No. 864754-07-4) is a sophisticated organic compound that has garnered significant attention in the field of chemical biology and pharmaceutical research. This compound, characterized by its intricate molecular structure, plays a pivotal role in the development of novel therapeutic agents and advanced synthetic methodologies. The unique combination of a piperazine ring and a benzoyl group substituted with a tetramethyl-1,3,2-dioxaborolan-2-yl moiety makes it a versatile intermediate in organic synthesis, particularly in cross-coupling reactions that are fundamental to modern drug discovery.

The tetramethyl-1,3,2-dioxaborolan-2-yl group is a key feature of this compound, providing a stable boronic acid equivalent that is highly reactive in Suzuki-Miyaura coupling reactions. These reactions are widely employed in the construction of complex molecular architectures, including biaryl compounds that are prevalent in many pharmacologically active molecules. The benzoyl component of the compound contributes to its ability to act as a chelating agent and a structural scaffold for further functionalization. This dual functionality makes 1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]piperazine an invaluable tool in the chemist's arsenal.

In recent years, there has been a surge in research focused on developing more efficient and selective synthetic routes for complex organic molecules. The use of boronic acids and their derivatives has been particularly prominent in this area. The tetramethyl-1,3,2-dioxaborolan-2-yl group enhances the stability of boronic acids under various reaction conditions, thereby improving yields and reducing unwanted side reactions. This has led to the adoption of this moiety in numerous industrial and academic settings where precision and efficiency are paramount.

The piperazine ring in 1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]piperazine also contributes to its significance in pharmaceutical research. Piperazine derivatives are well-known for their biological activity and have been incorporated into drugs targeting various diseases. The structural flexibility of the piperazine ring allows for the facile introduction of additional functional groups, making it an ideal platform for drug design. Recent studies have highlighted the potential of piperazine-based compounds as modulators of enzyme activity and as scaffolds for antiviral and anti-inflammatory agents.

The benzoyl group further enhances the potential applications of this compound by providing a site for further chemical modification. For instance, it can be used to introduce fluorescence tags or other reporter groups for biochemical assays. Additionally, the benzoyl group can participate in hydrogen bonding interactions, which is crucial for designing molecules with specific binding properties. These characteristics make 1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]piperazine a valuable building block in the development of novel materials and bioactive compounds.

Recent advancements in computational chemistry have also played a significant role in understanding the reactivity and potential applications of 1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]piperazine. Molecular modeling studies have provided insights into how this compound interacts with biological targets at the atomic level. These insights have been instrumental in guiding synthetic modifications aimed at improving binding affinity and selectivity. Furthermore, computational methods have been used to predict the outcomes of various chemical reactions involving this compound, thereby accelerating the drug discovery process.

The synthesis of 1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]piperazine involves several key steps that highlight its complexity as a chemical entity. The introduction of the tetramethyl-1,3,2-dioxaborolan-2-yl group requires careful control over reaction conditions to ensure high yield and purity. This is often achieved through palladium-catalyzed cross-coupling reactions under inert atmospheres. The subsequent functionalization of the benzoyl group further demonstrates the compound's versatility as a synthetic intermediate.

In conclusion, 1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoyl]piperazine (CAS No. 864754-07-4) is a multifaceted compound with significant implications in chemical biology and pharmaceutical research. Its unique structural features make it an excellent candidate for use as an intermediate in organic synthesis and as a scaffold for drug design. The ongoing research into its reactivity and potential applications continues to expand its utility across various scientific disciplines.

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• 400727-57-3(4-(N,N-Dimethylaminocarbonyl)phenylboronic acid, pinacol ester)
• 832114-06-4(4-(4-Methylpiperazine-1-carbonyl)phenylboronic Acid Pinacol Ester)
• 1073353-57-7(4-(N-Benzylaminocarbonyl)phenylboronic Acid Pinacol Ester)
• 840521-76-8(3-(2-(Dimethylamino)ethylcarbamoyl)phenylboronic acid, pinacol ester)
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• 832114-11-1(4-(2-(Dimethylamino)ethylcarbamoyl)phenylboronic acid, pinacol ester)
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