(E)-3,5-dichloro-4-(3-ethoxy-2-methyl-3-oxoprop-1-enyl)benzoic acid

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Cat Number

INT1110767899

CAS Number

1110767-89-9

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Product Detail Description Customer Q&A

CAS Number

1110767-89-9

Storage

Sealed in dry, room temperature

Synonyms

3,5-Dichloro-4-[(1E)-3-ethoxy-2-methyl-3-oxo-1-propen-1-yl]benzoic acid; 3,5-dichloro-4-(3-ethoxy-2-methyl-3-oxoprop-1-enyl)benzoic acid; 4-((E)-2-(ethoxycarbonyl)prop-1-enyl)-3,5-dichlorobenzoic acid

Molecular Formula

C12H10Cl2O4

Molecular Weight

303.14

Smiles

CCOC(=O)/C(=C/C1=C(C=C(C=C1Cl)C(=O)O)Cl)/C

Appearance

White to off-white solid

Boiling Point

442.1℃

Relative Density

1.38

pKa

3.43

General Description

(E)-3,5-dichloro-4-(3-ethoxy-2-methyl-3-oxoprop-1-enyl)benzoic acid is a structurally complex aromatic derivative that integrates an alpha,beta-unsaturated ester functionality with a highly substituted benzoic acid core. This molecule features a rigid (E)-alkene linkage, which dictates its precise spatial geometry. It serves as a specialized pharmaceutical intermediate designed for the construction of advanced therapeutic agents where rigid, unsaturated linkers are essential for optimized binding and target recognition.

Mechanism of Action

As a sophisticated synthetic building block, (E)-3,5-dichloro-4-(3-ethoxy-2-methyl-3-oxoprop-1-enyl)benzoic acid functions as a platform for multi-step chemical assembly. The (E)-configured alkene serves as a rigid structural spacer, while the ethyl ester and the carboxylic acid groups provide orthogonal reactive sites for selective functionalization. In medicinal chemistry, this molecular architecture is used to mimic natural products or enzyme substrates, providing a scaffold that can be refined through further chemical transformations to achieve high specificity and affinity for its biological targets.

Application

(E)-3,5-dichloro-4-(3-ethoxy-2-methyl-3-oxoprop-1-enyl)benzoic acid is employed in the development of therapeutic molecules aimed at addressing complex chronic diseases, particularly those involving intricate protein-ligand interactions. Additionally, it serves as a valuable reagent in medicinal chemistry for the construction of diverse chemical libraries required for high-throughput screening and structure-activity relationship (SAR) studies of novel heterocyclic or macrocyclic therapeutic candidates.

What is the significance of the (E)-configuration in (E)-3,5-dichloro-4-(3-ethoxy-2-methyl-3-oxoprop-1-enyl)benzoic acid?

The (E)-configuration in it provides a specific, rigid three-dimensional orientation that is crucial for it to successfully interact with its intended biological target.

How do the chlorine atoms influence the reactivity of (E)-3,5-dichloro-4-(3-ethoxy-2-methyl-3-oxoprop-1-enyl)benzoic acid?

The chlorine atoms in it provide electronic stabilization to the aromatic core and contribute to the overall lipophilicity and binding profile of the final drug candidate.

What is the primary pharmaceutical use for (E)-3,5-dichloro-4-(3-ethoxy-2-methyl-3-oxoprop-1-enyl)benzoic acid?

It is primarily used as a key building block in the synthesis of advanced APIs, facilitating the construction of complex therapeutic molecules.

How should (E)-3,5-dichloro-4-(3-ethoxy-2-methyl-3-oxoprop-1-enyl)benzoic acid be stored?

It should be stored in a cool, dry place in a tightly sealed container, protected from light and moisture to prevent the hydrolysis of the ester or oxidation of the alkene.