molecular formula C16H17NO6 B031883 Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate CAS No. 88150-75-8

Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate

Cat. No.: B031883
CAS No.: 88150-75-8
M. Wt: 319.31 g/mol
InChI Key: RIGKLAOKQFKWNN-UHFFFAOYSA-N
Attention: For research use only. Not for human or veterinary use.
In Stock
  • Click on QUICK INQUIRY to receive a quote from our team of experts.
  • With the quality product at a COMPETITIVE price, you can focus more on your research.

Description

Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate is a complex organic compound characterized by the presence of an isoindoline-1,3-dione moiety

Preparation Methods

Synthetic Routes and Reaction Conditions

The synthesis of Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate typically involves the condensation of an aromatic primary amine with a maleic anhydride derivative, leading to the formation of the isoindoline-1,3-dione scaffold . Another approach involves the reaction of phthalic anhydride with glycine and acetic acid in the presence of triethylamine in toluene as a solvent .

Industrial Production Methods

Industrial production methods for this compound are not extensively documented, but they likely involve similar synthetic routes with optimization for large-scale production. This includes the use of efficient catalysts and solvent systems to maximize yield and purity.

Chemical Reactions Analysis

Types of Reactions

Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate undergoes various types of chemical reactions, including:

    Oxidation: This compound can be oxidized to introduce additional functional groups.

    Reduction: Reduction reactions can modify the isoindoline-1,3-dione moiety.

    Substitution: Electrophilic and nucleophilic substitution reactions can occur at various positions on the molecule.

Common Reagents and Conditions

Common reagents used in these reactions include oxidizing agents like potassium permanganate, reducing agents such as lithium aluminum hydride, and various nucleophiles and electrophiles for substitution reactions .

Major Products

The major products formed from these reactions depend on the specific conditions and reagents used. For example, oxidation can lead to the formation of carboxylic acids, while reduction can yield amines or alcohols.

Comparison with Similar Compounds

Similar Compounds

Uniqueness

Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate is unique due to its specific structure, which combines the isoindoline-1,3-dione moiety with an ethoxy and oxobutanoate group. This unique combination of functional groups imparts distinct chemical and biological properties, making it a valuable compound for various research and industrial applications .

Properties

IUPAC Name

ethyl 4-[2-(1,3-dioxoisoindol-2-yl)ethoxy]-3-oxobutanoate
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

InChI

InChI=1S/C16H17NO6/c1-2-23-14(19)9-11(18)10-22-8-7-17-15(20)12-5-3-4-6-13(12)16(17)21/h3-6H,2,7-10H2,1H3
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

InChI Key

RIGKLAOKQFKWNN-UHFFFAOYSA-N
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Canonical SMILES

CCOC(=O)CC(=O)COCCN1C(=O)C2=CC=CC=C2C1=O
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

Molecular Formula

C16H17NO6
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

DSSTOX Substance ID

DTXSID90431687
Record name Ethyl 4-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethoxy]-3-oxobutanoate
Source EPA DSSTox
URL https://comptox.epa.gov/dashboard/DTXSID90431687
Description DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Molecular Weight

319.31 g/mol
Source PubChem
URL https://pubchem.ncbi.nlm.nih.gov
Description Data deposited in or computed by PubChem

CAS No.

88150-75-8
Record name Ethyl 4-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethoxy]-3-oxobutanoate
Source CAS Common Chemistry
URL https://commonchemistry.cas.org/detail?cas_rn=88150-75-8
Description CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society.
Explanation The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
Record name Ethyl 4-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethoxy]-3-oxobutanoate
Source EPA DSSTox
URL https://comptox.epa.gov/dashboard/DTXSID90431687
Description DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.
Record name Butanoic acid, 4-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethoxy]-3-oxo-, ethyl ester
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.

Synthesis routes and methods I

Procedure details

To a slurry of sodium hydride (57% dispersion in oil, 66.1 g; 1.57M), in tetrahydrofuran (500 ml) cooled to 0° under nitrogen was added 2-phthalimidoethanol (150 g; 0.785M) followed by ethyl 4-chloroacetoacetate (129 g; 0.785M) in tetrahydrofuran (250 ml) over 1 hour. The mixture was stirred at room temperature overnight then poured into a mixture of 1M hydrochloric acid (800 ml) and ethyl acetate (750 ml). The organic phase was separated and the solvent was evaporated at reduced pressure. The residue separated into two layers and the upper layer of mineral oil was removed to leave the title compound (243 g) as a crude product which was used without further purification.
Quantity
66.1 g
Type
reactant
Reaction Step One
Quantity
500 mL
Type
solvent
Reaction Step One
Quantity
150 g
Type
reactant
Reaction Step Two
Quantity
129 g
Type
reactant
Reaction Step Three
Quantity
250 mL
Type
solvent
Reaction Step Three
Quantity
800 mL
Type
reactant
Reaction Step Four
Quantity
750 mL
Type
solvent
Reaction Step Four

Synthesis routes and methods II

Procedure details

Sodium hydride (57% [by weight] in oil, 66.1 g) was stirred in dry tetrahydrofuran (500 ml) under nitrogen at -10° while N-(2-hydroxyethyl)phthalimide (150 g) was added. To this slurry was added at -10° a solution of ethyl 4-chloroacetoacetate (129.3 g), in dry tetrahydrofuran, over 1 hour. The reaction mixture was then allowed to warm to room temperature and stirring was continued for 18 hours. This mixture was poured into 1N hydrochloric acid (800 ml) and ethyl acetate was added (750 ml). The aqueous layer was washed with ethyl acetate (300 ml) and the organic solutions were combined. After washing with water (300 ml), the ethyl acetate was evaporated to give the title compound as a crude oil (243 g), sufficiently pure for further use.
Quantity
66.1 g
Type
reactant
Reaction Step One
Quantity
150 g
Type
reactant
Reaction Step One
Quantity
500 mL
Type
solvent
Reaction Step One
Quantity
129.3 g
Type
reactant
Reaction Step Two
Quantity
800 mL
Type
reactant
Reaction Step Three
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Three
Quantity
0 (± 1) mol
Type
solvent
Reaction Step Four

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

Reactant of Route 1
Reactant of Route 1
Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate
Reactant of Route 2
Reactant of Route 2
Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate
Reactant of Route 3
Reactant of Route 3
Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate
Reactant of Route 4
Reactant of Route 4
Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate
Reactant of Route 5
Reactant of Route 5
Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate
Reactant of Route 6
Ethyl 4-(2-(1,3-dioxoisoindolin-2-yl)ethoxy)-3-oxobutanoate

Disclaimer and Information on In-Vitro Research Products

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.