1-(Tetrahydro-2-furyl)-3-(1-naphthyl)propane-2,2-dicarboxylic acid
[CAS# 113527-39-2]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Furan and pyran
• Name: 1-(Tetrahydro-2-furyl)-3-(1-naphthyl)propane-2,2-dicarboxylic acid
• Synonyms: 2-(naphthalen-1-ylmethyl)-2-(oxolan-2-ylmethyl)propanedioic acid
• Molecular Formula: C₁₉H₂₀O₅
• Molecular Weight: 328.36
• CAS Registry Number: 113527-39-2
• SMILES: C1CC(OC1)CC(CC2=CC=CC3=CC=CC=C32)(C(=O)O)C(=O)O

Properties

• Solubility: 53.46 mg/L (25 ºC water)
• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.625, Calc.^*
• Melting point: 217.62 ºC
• Boiling Point: 510.74 ºC, 529.4±45.0 ºC (760 mmHg), Calc.^*
• Flash Point: 191.3±22.2 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501

Discovory and Applicatios

1-(Tetrahydro-2-furyl)-3-(1-naphthyl)propane-2,2-dicarboxylic acid is a polyfunctional organic compound that contains both aromatic and heterocyclic features along with two carboxylic acid groups. Its molecular formula is C₁₇H₁₈O₅, and its structure consists of a naphthalene moiety substituted at the 1-position, a tetrahydrofuran ring (also referred to as tetrahydro-2-furyl), and a propane-2,2-dicarboxylic acid backbone.

The compound contains a central three-carbon chain in which the second carbon (the 2-position) bears two carboxylic acid groups (–COOH), making it a geminal dicarboxylic acid. The terminal carbons are substituted: one end is attached to a tetrahydrofuran ring, a saturated five-membered ether with four carbon atoms and one oxygen, while the other end is connected to a 1-naphthyl group, derived from naphthalene, a fused aromatic hydrocarbon with two benzene rings.

This compound is best categorized as a substituted malonic acid derivative due to the geminal dicarboxylic acid structure at the 2-position. Such structural features are often found in synthetic intermediates and compounds with potential biological activity. The combination of hydrophobic (naphthyl and tetrahydrofuryl) and hydrophilic (dicarboxylic acid) components allows for unique physicochemical properties, including amphiphilicity and potential interactions with both polar and nonpolar molecular targets.

The synthesis of this compound typically involves alkylation or acylation reactions starting from malonic acid or its esters, followed by substitution with naphthyl and tetrahydrofuryl groups. In classical organic synthesis, gem-dicarboxylic acids such as this one are accessed via alkylation of malonates, followed by hydrolysis and acidification.

Analytical methods used to characterize this compound include nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and infrared (IR) spectroscopy. In ²H NMR, characteristic signals from the aromatic protons of the naphthalene ring and the ring methylene groups of the tetrahydrofuran are observed, along with the proton environments near the carboxylic acid groups. ³C NMR reveals the carbon atoms of the aromatic ring system, the aliphatic chain, and the two carboxylic acids. The carboxyl groups typically show strong C=O stretching in the IR spectrum.

The compound has been reported in the literature primarily in the context of synthetic organic chemistry and structure-activity relationship (SAR) studies. Some derivatives of malonic acids containing aryl and heterocyclic groups have been explored for their potential biological activities, such as inhibition of enzymes or as ligands in receptor studies. However, this specific compound does not have broad pharmacological applications established in clinical settings.

Due to the presence of two acidic functional groups, 1-(tetrahydro-2-furyl)-3-(1-naphthyl)propane-2,2-dicarboxylic acid is generally soluble in polar solvents such as methanol, ethanol, or dimethyl sulfoxide (DMSO), and forms salts with bases like sodium or potassium hydroxide. The dicarboxylic acid functionality allows for the formation of esters and amides, enabling its use as a synthetic intermediate for more complex organic molecules.

In conclusion, 1-(tetrahydro-2-furyl)-3-(1-naphthyl)propane-2,2-dicarboxylic acid is a structurally diverse organic compound combining aromatic, heterocyclic, and dicarboxylic acid motifs. It serves as a versatile building block in organic synthesis and a candidate for research in the development of functionalized molecules with potential chemical or biological utility.