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Mar. 25th 2025
1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde, CAS 137076-22-3, The molecular formula C11H19NO3 is an important organic compound with wide applications in the fields of medicine and organic synthesis. This compound consists of 11 carbon atoms, 19 hydrogen atoms, 1 nitrogen atom, and 3 oxygen atoms. The molecular weight of 213.273 is the average molecular weight of the compound, and the precise mass provides more accurate mass information. It usually exists in the form of a white solid or colorless to pale yellow powder, and can be used as a reactant or catalyst in various chemical reactions in organic synthesis. It has a wide range of applications in the fields of medicine, organic synthesis, and chemical engineering. As a pharmaceutical intermediate, it can be used to synthesize various compounds with pharmacological activity; As an organic synthesis raw material, it can participate in various chemical reactions and construct complex molecular structures; As a chemical raw material, it can be used to synthesize various fine chemicals and pesticides.
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C.F |
C11H19NO3 |
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E.M |
213.14 |
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M.W |
213.28 |
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m/z |
213.14 (100.0%), 214.14 (11.9%) |
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E.A |
C, 61.95; H, 8.98; N, 6.57; O, 22.50 |
1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde (CAS number: 137076-22-3), also known as N-BOC-4-aldehyde pyridine, 1-BOC-piperidine-4-carboxaldehyde, etc., is an important organic compound with wide applications in the fields of medicine, organic synthesis, and chemical engineering.
1, Applications in the field of medicine
Selective MAO inhibitors
Monoamine oxidase (MAO) is an enzyme involved in neurotransmitter metabolism, and its activity is closely related to cardiovascular, neurological, and tumor diseases. By inhibiting MAO, the levels of neurotransmitters can be regulated to achieve the goal of treating diseases. It can be used as a raw material for synthesizing selective MAO-A and MAO-B inhibitors. These inhibitors can selectively inhibit the activity of MAO, thereby reducing the degradation of neurotransmitters and increasing their concentration in the body, achieving the effect of treating diseases.
Treatment of central nervous system diseases
Research has shown that derivatives of this substance have potential in the treatment of certain central nervous system diseases. For example, mouse experimental studies have shown that 1-propargyl-4-styrylpiperidine (a compound synthesized from this substance) has therapeutic potential for central nervous system diseases. These compounds can improve disease symptoms or delay disease progression by regulating the levels of neurotransmitters or receptor activity.
Anti inflammatory and sEH inhibitors
It can also be used to synthesize compounds with anti-inflammatory and sEH inhibitory activities. These compounds can serve as pharmacophore leads for the development of novel anti-inflammatory drugs and sEH inhibitors. SEH is an enzyme involved in arachidonic acid metabolism, and its inhibitors can inhibit the conversion of arachidonic acid to inflammatory mediators, thereby reducing the inflammatory response. Meanwhile, sEH inhibitors can also prevent elevated blood pressure and have a protective effect on the cardiovascular system.
2, Applications in the field of organic synthesis
Synthesis of Polycyclic Indazole Derivatives
It can serve as an important intermediate for the synthesis of polycyclic indazole derivatives. Polycyclic indazole derivatives are a class of compounds with a wide range of pharmacological activities, including anti-tumor, anti-inflammatory, antibacterial, and other activities. By introducing its functional groups, the structure of polycyclic indazole derivatives can be constructed and their pharmacological activity can be further optimized.
Wittig reaction
The aldehyde group of this substance can participate in Wittig reactions to generate olefin compounds. The Wittig reaction is an important organic synthesis reaction that generates olefins with specific structures through the reaction of aldehydes or ketones with phosphoylides. This reaction has a wide range of applications in organic synthesis and can be used to construct complex molecular structures.
Constructing complex molecular structures
The functional groups of this substance (such as aldehyde groups, tert butoxycarbonyl groups, etc.) can react with other compounds to construct complex molecular structures. These complex molecular structures have wide applications in organic synthesis and medicinal chemistry, and can be used to develop new drugs, catalysts, and materials.
1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde in Computational Chemistry and Spectroscopy: A Probe for Revealing Hidden Interactions
1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde (CAS number 137076-22-3, molecular formula C ₁₁ H ₁₉ NO ∝), as a key intermediate in organic synthesis, is endowed with unique chemical activity due to its structural features - the N-Boc protecting group of the pyridine ring and the aldehyde group at position 4. In drug development, it is not only the core skeleton for synthesizing polycyclic indazole ERK inhibitors, but also an important participant in constructing olefin structures through Wittig reactions. However, its true value goes far beyond its synthetic tools: through the deep integration of computational chemistry and spectroscopy, 1-tert-Butoxycarbonyl-4-piperidine-carboxaldehyde can serve as a "molecular probe" that reveals the hidden interaction mechanisms between molecules, providing key clues for drug design, materials science, and even life sciences.
Molecular structure analysis: the cornerstone of probe design
Core structural features
The molecular structure of 1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde contains three key components:
Piperidine ring: As a six membered nitrogen-containing heterocyclic ring, its chair conformation determines the stereochemical properties of the molecule. Computational chemistry studies have shown that the N-Boc protecting group (tert butoxycarbonyl) of the pyridine ring stabilizes the conformation of the ring through steric hindrance effect, while its electronic effect (electron withdrawing induction effect) affects the reactivity of the aldehyde group.
Core structural features
Aldehyde group (- CHO): As a polar functional group, the carbon oxygen double bond (C=O) of aldehyde group has strong polarity (δ ⁺ C - δ ⁻ O), making it a hydrogen bond donor and acceptor, which can form dynamic interactions with protein residues (such as the ε - amino group of lysine and the carboxyl group of aspartic acid).
Tert butoxycarbonyl (Boc): As a protecting group, the Boc group is connected to the pyridine nitrogen atom through an ester bond (C (=O) O-tBu), and its larger tert butyl group (tBu) can shield the alkalinity of the nitrogen atom and prevent side reactions during the synthesis process.
Molecular Dynamics Simulation: Revealing Conformational Flexibility
The dynamic behavior of 1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde in solution can be revealed through molecular dynamics (MD) simulations. For example:
Flip of Piperidine Ring: In methanol solution, the pyridine ring may undergo a "chair boat" conformational flip, with an energy barrier of approximately 10-15 kcal/mol (calculated by density functional theory DFT). This flipping may affect the binding mode between aldehyde groups and target molecules.
Molecular Dynamics Simulation: Revealing Conformational Flexibility
Rotational degrees of freedom of aldehyde group: The C-C single bond of aldehyde group (connecting the pyridine ring and aldehyde group) has a high rotational degree of freedom, and its rotational potential barrier is only 2-3 kcal/mol (calculated by AM1 semi empirical method), resulting in multiple orientations of aldehyde group in space, which may enhance its adaptive binding with the target.
Computational Chemistry: A 'Virtual Microscope' for Predicting Hidden Interactions
Molecular Docking: Prediction of Target Binding Modes
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1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde As a drug intermediate, its binding mode with target proteins can be predicted through molecular docking technology. For example:
Binding of ERK inhibitors: In the synthesis of polycyclic indazole based ERK inhibitors, the aldehyde group of 1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde may bind to the Asp167 residue of ERK kinase through hydrogen bonding, while the hydrophobic side chain of the pyridine ring is inserted into the hydrophobic region of the ATP binding pocket. According to the AutoDock Vina docking software calculation, the binding free energy (Δ G) of the molecule is approximately -8.5 kcal/mol, indicating its moderate binding ability.
Binding of GPR119 agonists: In the synthesis of selective GPR119 agonists, aldehyde groups may enhance the molecular excitatory activity by forming salt bridges with the Arg241 residue of GPR119. The molecular docking results showed that the binding mode of the molecule is highly similar to known agonists (such as AR231453), suggesting that it may have similar biological activity.
Quantum Chemistry Calculation: Deep Analysis of Electronic Structure
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By using quantum chemical calculations (such as DFT methods), the electronic distribution characteristics of 1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde can be revealed, and its reaction activity and interaction mechanism can be predicted. For example:
Frontline molecular orbital analysis: Calculations at the B3LYP/6-31G (d) level indicate that the highest occupied molecular orbital (HOMO) of the molecule is mainly distributed on the nitrogen atom of the pyridine ring and the oxygen atom of the aldehyde group, while the lowest unoccupied molecular orbital (LUMO) is concentrated on the carbon atom of the aldehyde group. This electronic distribution characteristic indicates that the carbon atoms of aldehyde groups have high electrophilicity and are susceptible to attack by nucleophiles such as thiol groups in proteins.
Static potential diagram analysis: The static potential diagram generated by Multiwfn software shows that the oxygen atom surface of the aldehyde group exhibits a strong negative potential (-50 kcal/mol), while the nitrogen atom surface of the pyridine ring exhibits a weak positive potential (+20 kcal/mol). This charge distribution characteristic enables it to act as both a hydrogen bond donor and acceptor, participating in multiple non covalent interactions.
Molecular Dynamics Simulation: Tracking of Dynamic Interactions
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In a solution environment, the interaction between 1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde and target molecules is dynamic. Through MD simulation, the dynamic changes of these interactions can be tracked. For example:
Analysis of Hydration: In the explicit solvent model, the oxygen atom of the aldehyde group can form a hydrogen bond network with surrounding water molecules, with an average hydrogen bond lifetime of approximately 0.5 ps (calculated using the gmx hbond tool). This hydration may affect the binding affinity between the molecule and the target.
Calculation of conformational entropy: By calculating the conformational entropy (Sconf) of a molecule, the contribution of its conformational flexibility to the binding free energy can be evaluated. For example, when binding to ERK kinase, the conformational entropy of the molecule decreases by about 2 kcal/mol (calculated by MM-PBSA method), indicating that conformational fixation is an important driving force in the binding process.
Spectroscopy: The 'gold standard' for experimentally verifying covert interactions
Nuclear Magnetic Resonance (NMR) Spectroscopy: Interaction Analysis at Atomic Level Resolution
NMR spectroscopy is one of the most powerful tools for studying intermolecular interactions. For 1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde, NMR can provide the following information:
Chemical shift change: When a molecule binds to a target protein, the chemical shift of the aldehyde proton (δ 9.8 ppm) may shift (Δδ± 0.1 ppm), indicating a change in its electronic environment. For example, when binding to ERK kinase, the chemical shift of aldehyde proton towards low field shifts by 0.05 ppm, indicating the formation of hydrogen bonds with Asp167 residue.
NOE effect analysis: Through the nuclear Auerbach effect (NOE) experiment, the spatial proximity between different atoms in a molecule can be determined. For example, a strong NOE signal was observed between the aldehyde proton and the alpha proton of the pyridine ring (δ 3.5 ppm), indicating that the two are spatially close (about 3 Å apart), which is consistent with the predicted conformation of molecular docking.
Two dimensional NMR (2D NMR): Through HSQC or HMBC experiments, the correlation between carbon hydrogen or carbon carbon in molecules can be established, further confirming their structures. For example, through HMBC experiments, long-range coupling between the aldehyde carbon (δ 190 ppm) and the β - carbon of the pyridine ring (δ 40 ppm) can be observed, confirming their connection mode.
Infrared Spectroscopy (IR): Fingerprint of Functional Group Vibration
IR spectroscopy can provide vibrational information of functional groups in molecules for monitoring structural changes caused by interactions. For example:
C=O stretching vibration of aldehyde group: In free molecules, the C=O stretching vibration peak of aldehyde group is located at 1720 cm ⁻¹ (predicted by DFT calculation). When the molecule binds to the target protein, the peak may shift towards lower wavenumbers (up to 1700 cm ⁻¹), indicating a decrease in the strength of the C=O bond, possibly due to hydrogen bonding formation.
C-N stretching vibration of pyridine ring: The C-N stretching vibration peak of pyridine ring is located at 1250 cm ⁻¹, and its intensity change can reflect the conformational change of the ring. For example, when bound to GPR119 agonists, the peak intensity increases, indicating a more rigid conformation of the ring.
Circular dichroism spectroscopy (CD): conformational fingerprint of chiral molecules
If the derivative of 1-tert-Butoxycarbonyl-4-piperidinecarboxaldehyde has a chiral center, CD spectroscopy can be used to analyze its absolute configuration and conformation. For example:
Cotton effect analysis: In the wavelength range of 200-300 nm, the CD spectrum of chiral molecules may exhibit positive or negative Cotton effects, whose sign is related to the absolute configuration. By comparing with the CD spectra of known chiral molecules, their configurations can be determined.
Conformation dependent CD signal: When a molecule binds to a target protein, its CD spectrum may change, reflecting conformational adjustments. For example, when combined with HDAC inhibitors, the CD signal is enhanced at 220 nm, indicating an increase in alpha helix structure.
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