(R)-3-(methylamino)-1-phenylpropan-1-ol
Overview
Description
®-3-(methylamino)-1-phenylpropan-1-ol is an organic compound with significant importance in various fields of chemistry and pharmacology. It is a chiral molecule, meaning it has a specific three-dimensional arrangement that is not superimposable on its mirror image. This compound is known for its applications in the synthesis of pharmaceuticals and as an intermediate in organic synthesis.
Scientific Research Applications
®-3-(methylamino)-1-phenylpropan-1-ol has a wide range of applications in scientific research:
Chemistry: It is used as an intermediate in the synthesis of various organic compounds, including pharmaceuticals and agrochemicals.
Biology: The compound is studied for its potential effects on biological systems, including its interactions with enzymes and receptors.
Medicine: It serves as a precursor in the synthesis of drugs used to treat conditions such as asthma and nasal congestion.
Preparation Methods
Synthetic Routes and Reaction Conditions: The synthesis of ®-3-(methylamino)-1-phenylpropan-1-ol can be achieved through several methods. One common approach involves the reductive amination of 1-hydroxy-1-phenylpropan-2-one with methylamine. This reaction typically requires a catalyst, such as platinum or palladium, and is carried out under hydrogenation conditions . The stereoselectivity of this reaction is crucial, as it determines the specific enantiomer produced.
Industrial Production Methods: In an industrial setting, the production of ®-3-(methylamino)-1-phenylpropan-1-ol may involve dynamic kinetic resolution (DKR) techniques. These methods utilize enzymes or metal catalysts to selectively produce the desired enantiomer while converting the undesired enantiomer back to the starting material . This approach enhances the overall yield and efficiency of the production process.
Chemical Reactions Analysis
Types of Reactions: ®-3-(methylamino)-1-phenylpropan-1-ol undergoes various chemical reactions, including:
Oxidation: The compound can be oxidized to form corresponding ketones or aldehydes.
Reduction: It can be reduced to form secondary or tertiary amines.
Substitution: The hydroxyl group can be substituted with other functional groups, such as halides or esters.
Common Reagents and Conditions:
Oxidation: Common oxidizing agents include potassium permanganate and chromium trioxide.
Reduction: Reducing agents such as sodium borohydride or lithium aluminum hydride are typically used.
Substitution: Reagents like thionyl chloride or phosphorus tribromide can facilitate substitution reactions.
Major Products: The major products formed from these reactions depend on the specific conditions and reagents used. For example, oxidation may yield ketones or aldehydes, while reduction can produce secondary or tertiary amines .
Mechanism of Action
The mechanism of action of ®-3-(methylamino)-1-phenylpropan-1-ol involves its interaction with specific molecular targets, such as enzymes or receptors. The compound can act as an agonist or antagonist, depending on the target and the context of its use. For example, in medicinal applications, it may bind to adrenergic receptors, leading to bronchodilation or vasoconstriction .
Comparison with Similar Compounds
- ®-3-(methylamino)piperidine-1-carboxylate
- ®-3-(methylamino)butan-1-ol
- ®-2-(methylamino)-2-phenylacetic acid
Comparison: ®-3-(methylamino)-1-phenylpropan-1-ol is unique due to its specific chiral configuration and the presence of both a hydroxyl and a methylamino group. This combination of functional groups allows it to participate in a wide range of chemical reactions and makes it a valuable intermediate in organic synthesis. Compared to similar compounds, it offers distinct advantages in terms of reactivity and selectivity in various applications.
Properties
IUPAC Name |
(1R)-3-(methylamino)-1-phenylpropan-1-ol |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C10H15NO/c1-11-8-7-10(12)9-5-3-2-4-6-9/h2-6,10-12H,7-8H2,1H3/t10-/m1/s1 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
XXSDCGNHLFVSET-SNVBAGLBSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CNCCC(C1=CC=CC=C1)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Isomeric SMILES |
CNCC[C@H](C1=CC=CC=C1)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C10H15NO |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Weight |
165.23 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
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Retrosynthesis Analysis
AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.
One-Step Synthesis Focus: Specifically designed for one-step synthesis, it provides concise and direct routes for your target compounds, streamlining the synthesis process.
Accurate Predictions: Utilizing the extensive PISTACHIO, BKMS_METABOLIC, PISTACHIO_RINGBREAKER, REAXYS, REAXYS_BIOCATALYSIS database, our tool offers high-accuracy predictions, reflecting the latest in chemical research and data.
Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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Please be aware that all articles and product information presented on BenchChem are intended solely for informational purposes. The products available for purchase on BenchChem are specifically designed for in-vitro studies, which are conducted outside of living organisms. In-vitro studies, derived from the Latin term "in glass," involve experiments performed in controlled laboratory settings using cells or tissues. It is important to note that these products are not categorized as medicines or drugs, and they have not received approval from the FDA for the prevention, treatment, or cure of any medical condition, ailment, or disease. We must emphasize that any form of bodily introduction of these products into humans or animals is strictly prohibited by law. It is essential to adhere to these guidelines to ensure compliance with legal and ethical standards in research and experimentation.
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