1218791-13-9 | 4-(Benzyloxycarbonylamino)-2-fluorophenylboronic acid, pinacol ester

CAS:1218791-13-9 | 4-(Benzyloxycarbonylamino)-2-fluorophenylboronic acid, pinacol ester,Description

Benzyl (3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate is a chemical compound with the molecular formula C20H23BFNO4. It has a molecular weight of 371.2 g/mol. This compound is also known by other names such as 4-(Cbz-Amino)-2-fluorophenylboronic acid, pinacol ester, and benzyl N-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate.

Synthesis Analysis

The synthesis of this compound involves a two-step substitution reaction. The structure of the compound is verified by FTIR, 1H and 13C NMR, and MS.

Molecular Structure Analysis

The single crystal structure of the compound is gauged by X-ray diffraction and subjected to crystallographic and conformational analyses. Density functional theory (DFT) is applied to further calculate the molecular structure and compare it with X-ray values. The result of the conformational analysis shows that the molecular structure optimized by DFT is identical with the single crystal structure determined by single crystal X-ray diffraction.

Physical And Chemical Properties Analysis

The compound has a molecular weight of 371.2 g/mol. It has one hydrogen bond donor.

Scientific Research Applications

• Synthesis and Crystal Structure Study

  • Field : Structural Chemistry.
  • Application : These compounds are obtained by substitution reactions and their structures are confirmed by FTIR, 1H and 13C NMR spectroscopy, and mass spectrometry. Single crystals of the compounds are measured by X-ray diffraction and subjected to crystallographic and conformational analyses.
  • Methods : The molecular structures are further calculated using density functional theory (DFT), which were compared with the X-ray diffraction value.
  • Results : The results of the conformational analysis indicate that the molecular structures optimized by DFT are consistent with the crystal structures determined by single crystal X-ray diffraction.

• Drug Research

  • Field : Pharmacology.
  • Application : Boric acid compounds are often used as enzyme inhibitors or specific ligand drugs which can be used not only in the treatment of tumors and microbial infections, but also in the design of anticancer drugs.
  • Methods : In the research of anticancer drugs, enzymes produced by boric acid compounds had highly reactive oxygen species, which could lead to apoptosis of the HCT116 human colon cancer cell.
  • Results : It was found that these compounds could lead to apoptosis and necrosis of HeLa cells in the process of inducing oxidative stress.

• Organic Synthesis Reactions

  • Field : Organic Chemistry.
  • Application : Boronic acid pinacol ester compounds are significant reaction intermediates which have many applications in carbon-carbon coupling and carbon heterocoupling reactions.
  • Methods : Because of their unique structure, they have good biological activity and pharmacological effects. They have been widely used in boron neutron capture therapy and feedback control drug transport polymers in cancer treatment.
  • Results : Arylboronic acid is economical and easy to obtain, and it is stable to water and air. It is one of the important nucleophiles in the Suzuki reaction and has a wide range of applications.

• LCMS Technique

  • Field : Analytical Chemistry.
  • Application : Boronate esters are used as model compounds in the study of the stability of boronate esters in different alcohols using the LCMS technique.
  • Methods : The stability of boronate esters in different alcohols is studied using the LCMS technique.
  • Results : This study provides valuable information about the stability of boronate esters in different alcohols.

• Palladium-Catalyzed Methylation

  • Field : Organic Chemistry.
  • Application : Boronate esters are used as substrates in the study of palladium-catalyzed methylation of heteroaryl boronate esters using iodomethane.
  • Methods : The palladium-catalyzed methylation of heteroaryl boronate esters is studied using iodomethane.
  • Results : This study provides valuable information about the palladium-catalyzed methylation of heteroaryl boronate esters.

• Synthesis of tert-Butyl 4- (4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate

  • Field : Organic Synthesis.
  • Application : The title compound is synthesized from 1-Boc-4- (4-Iodo-1H-pyrazol-1-yl)piperidine and 1-4,4,4’,4’,5,5,5’,5’-Octamethyl-2,2’-bi (1,3,2-dioxaborolane), which can also be obtained by purification and isolation from tert-Butyl 4- ((methylsulfonyl)oxy)piperidine-1-carboxylate.
  • Methods : The title compound is synthesized through a two-step substitution reaction.
  • Results : The successful synthesis of the title compound provides a new method for the synthesis of similar compounds.

• Fluorescent Probes

  • Field : Biochemistry.
  • Application : Boric acid compounds can also be used as fluorescent probes to identify hydrogen peroxide, saccharides, copper and fluorine ions, and catecholamine substances.
  • Methods : The fluorescent properties of these compounds are studied using various spectroscopic techniques.
  • Results : These studies provide valuable information about the potential use of these compounds as fluorescent probes.

• Glycol Protection

  • Field : Organic Chemistry.
  • Application : In the organic synthesis of drugs, boric acid compounds are often used in glycol protection.
  • Methods : The protective properties of these compounds are studied using various chemical reactions.
  • Results : These studies provide valuable information about the potential use of these compounds in glycol protection.

• Asymmetric Synthesis of Amino Acids

  • Field : Biochemistry.
  • Application : Boric acid compounds are often used in the asymmetric synthesis of amino acids.
  • Methods : The synthetic properties of these compounds are studied using various chemical reactions.
  • Results : These studies provide valuable information about the potential use of these compounds in the asymmetric synthesis of amino acids.

• Diels–Alder and Suzuki Coupling Reactions

  • Field : Organic Chemistry.
  • Application : Boric acid compounds are often used in Diels–Alder and Suzuki coupling reactions.
  • Methods : The reactivity of these compounds is studied using various chemical reactions.
  • Results : These studies provide valuable information about the potential use of these compounds in Diels–Alder and Suzuki coupling reactions.

• Boron Neutron Capture Therapy

  • Field : Medical Physics.
  • Application : Boronic acid pinacol ester compounds have been widely used in boron neutron capture therapy.
  • Methods : The therapeutic properties of these compounds are studied using various medical techniques.
  • Results : These studies provide valuable information about the potential use of these compounds in boron neutron capture therapy.

• Feedback Control Drug Transport Polymers

  • Field : Pharmacology.
  • Application : Boronic acid pinacol ester compounds have been widely used in feedback control drug transport polymers in cancer treatment.
  • Methods : The therapeutic properties of these compounds are studied using various medical techniques.
  • Results : These studies provide valuable information about the potential use of these compounds in feedback control drug transport polymers.

Future Directions

Boronic acid pinacol ester compounds, which this compound is a derivative of, have many applications in carbon-carbon coupling and carbon heterocoupling reactions. They have been widely used in boron neutron capture therapy and feedback control drug transport polymers in cancer treatment. Fluorine-containing compounds are also widely used in medicine. Therefore, the future research directions could involve exploring more applications of this compound in these areas.

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