1-Isopropylazetidin-3-ol
Overview
Description
1-Isopropylazetidin-3-ol is a chemical compound with the molecular formula C6H13NO and a molecular weight of 115.18 g/mol It is a member of the azetidine family, which are four-membered nitrogen-containing heterocycles
Scientific Research Applications
1-Isopropylazetidin-3-ol has several scientific research applications:
Chemistry: It serves as a building block for the synthesis of more complex molecules and heterocyclic compounds.
Biology: It is used in the study of enzyme inhibitors and as a potential scaffold for drug design.
Industry: It is used in the development of new materials and as a precursor for various industrial chemicals.
Safety and Hazards
The safety data sheet for 1-Isopropylazetidin-3-ol indicates that it is classified as a flammable liquid (Category 3, H226) . The safety data sheet for this compound hydrochloride indicates potential hazards including acute toxicity (H302), skin irritation (H315), eye irritation (H319), and specific target organ toxicity following single exposure (H335) .
Preparation Methods
Synthetic Routes and Reaction Conditions: 1-Isopropylazetidin-3-ol can be synthesized through several methods. One common approach involves the alkylation of primary amines with in situ generated bis-triflates of 2-substituted-1,3-propanediols . Another method includes the one-pot synthesis of nitrogen-containing heterocycles from alkyl dihalides and primary amines under microwave irradiation in an alkaline aqueous medium . Additionally, the direct alkylation of 1-azabicyclo[1.1.0]butane with organometal reagents in the presence of copper(II) triflate can rapidly provide bis-functionalized azetidines .
Industrial Production Methods: Industrial production methods for this compound are not extensively documented. the methods mentioned above can be adapted for large-scale synthesis with appropriate optimization of reaction conditions and purification processes.
Chemical Reactions Analysis
Types of Reactions: 1-Isopropylazetidin-3-ol undergoes various chemical reactions, including:
Oxidation: The hydroxyl group can be oxidized to form corresponding ketones or aldehydes.
Reduction: The compound can be reduced to form amines or other reduced derivatives.
Substitution: The hydroxyl group can be substituted with other functional groups using appropriate reagents.
Common Reagents and Conditions:
Oxidation: Reagents such as potassium permanganate or chromium trioxide can be used under acidic or basic conditions.
Reduction: Reagents like lithium aluminum hydride or sodium borohydride are commonly used.
Substitution: Reagents such as thionyl chloride or phosphorus tribromide can be employed for substitution reactions.
Major Products Formed:
Oxidation: Ketones or aldehydes.
Reduction: Amines or other reduced derivatives.
Substitution: Various substituted azetidines depending on the reagents used.
Mechanism of Action
The mechanism of action of 1-Isopropylazetidin-3-ol involves its interaction with specific molecular targets and pathways. The compound can act as an enzyme inhibitor by binding to the active site of enzymes, thereby preventing substrate binding and subsequent catalytic activity . Additionally, it may interact with cellular receptors and signaling pathways, leading to various biological effects .
Comparison with Similar Compounds
1-Isopropylazetidin-3-ol can be compared with other similar compounds, such as:
1-Methylazetidine: Similar in structure but with a methyl group instead of an isopropyl group.
1-Ethylazetidine: Contains an ethyl group instead of an isopropyl group.
1-Phenylazetidine: Contains a phenyl group, which significantly alters its chemical properties and applications.
Uniqueness: this compound is unique due to its specific isopropyl substitution, which imparts distinct steric and electronic properties. This uniqueness makes it a valuable compound for various synthetic and research applications.
Properties
IUPAC Name |
1-propan-2-ylazetidin-3-ol |
Source
|
|---|---|---|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI |
InChI=1S/C6H13NO/c1-5(2)7-3-6(8)4-7/h5-6,8H,3-4H2,1-2H3 |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
InChI Key |
XSGMJDQRZDWEPW-UHFFFAOYSA-N |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Canonical SMILES |
CC(C)N1CC(C1)O |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
Molecular Formula |
C6H13NO |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
DSSTOX Substance ID |
DTXSID60337783 |
Source
|
| Record name | 1-Isopropylazetidin-3-ol | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID60337783 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
Molecular Weight |
115.17 g/mol |
Source
|
| Source | PubChem | |
| URL | https://pubchem.ncbi.nlm.nih.gov | |
| Description | Data deposited in or computed by PubChem | |
CAS No. |
13156-06-4 |
Source
|
| Record name | 1-Isopropylazetidin-3-ol | |
| Source | EPA DSSTox | |
| URL | https://comptox.epa.gov/dashboard/DTXSID60337783 | |
| Description | DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology. | |
| Record name | 1-(propan-2-yl)azetidin-3-ol | |
| Source | European Chemicals Agency (ECHA) | |
| URL | https://echa.europa.eu/information-on-chemicals | |
| Description | The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness. | |
| Explanation | Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page. | |
Retrosynthesis Analysis
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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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