Description

(1r,4r)-Methyl 4-formylcyclohexanecarboxylate (CAS No. 37942-76-0) is a high-purity cyclohexane derivative with the molecular formula C₉H₁₄O₃. This compound, also known as methyl 4-formylcyclohexane-1-carboxylate, is a valuable intermediate in organic synthesis and pharmaceutical research. Its rigid cyclohexane backbone, combined with reactive formyl and ester functional groups, makes it a versatile building block for the preparation of complex molecules. The trans configuration (1r,4r) ensures stereochemical consistency, critical for applications requiring precise molecular geometry. Available in >98% purity by GC, this product is supplied as a clear, colorless to pale yellow liquid with a characteristic ester-like odor. Proper storage under inert atmosphere at 2-8°C is recommended to maintain stability.

Properties

• CAS Number: 37942-76-0
• Complexity: 169
• IUPAC Name: methyl 4-formylcyclohexanecarboxylate
• InChI: InChI=1S/C9H14O3/c1-12-9(11)8-4-2-7(6-10)3-5-8/h6-8H,2-5H2,1H3
• InChI Key: LARSGJZNVQJRMD-UHFFFAOYSA-N
• Exact Mass: 170.094294304
• Molecular Formula: C9H14O3
• Molecular Weight: 170.21
• SMILES: COC(=O)C1CCC(CC1)C=O
• Topological: 43.4
• Monoisotopic Mass: 170.094294304
• Synonyms: 54274-80-5, (1r,4r)-methyl 4-formylcyclohexanecarboxylate, 37942-76-0, methyl 4-formylcyclohexanecarboxylate, Methyl trans-4-Formylcyclohexanecarboxylate, trans-Methyl 4-formylcyclohexanecarboxylate, Methyl 4-formylcyclohexane-1-carboxylate, 4-FORMYL-CYCLOHEXANECARBOXYLIC ACID METHYL ESTER, trans-4-Formyl-cyclohexanecarboxylic acid methyl ester, MFCD12965033, MFCD16659932, 121317-96-2, Rel-methyl (1s,4s)-4-formylcyclohexane-1-carboxylate, Cyclohexanecarboxylic acid, 4-formyl-, methyl ester, trans-, Methyl4-formylcyclohexanecarboxylate, Cyclohexanecarboxylic acid, 4-formyl-, methyl ester, SCHEMBL108455, SCHEMBL142778, SCHEMBL15005440, DTXSID80969303, LARSGJZNVQJRMD-OCAPTIKFSA-N, LARSGJZNVQJRMD-UHFFFAOYSA-N, LARSGJZNVQJRMD-ZKCHVHJHSA-N, BCP27237, CS-D1139, methyl 4-formylcyclohexane carboxylate, methyl 4-formylcyclohexane-carboxylate, AKOS015851346, AKOS015999877, AKOS040804838, AT33186, SB11026, SB13987, Cis-methyl 4-formylcyclohexanecarboxylate, AS-43781, DA-16639, DS-15568, methyl cis-4-formylcyclohexane carboxylate, SY027704, SY279395, DB-208420, (trans)-methyl 4-formylcyclohexanecarboxylate, CS-0183744, Methyl trans-4-formylcyclohexane-1-carboxylate, 4-formylcyclohexane carboxylic acid methyl ester, methyl (1s,4s)-4-formylcyclohexane-1-carboxylate, METHYL CIS-4-FORMYLCYCLOHEXANE-1-CARBOXYLATE

Application

(1r,4r)-Methyl 4-formylcyclohexanecarboxylate serves as a key synthon in asymmetric synthesis of bioactive compounds, particularly in prostaglandin and terpenoid pathways. The formyl group enables reductive amination for chiral amine production, while the ester moiety allows for further functionalization via hydrolysis or transesterification. Researchers utilize this compound in medicinal chemistry for structure-activity relationship studies of constrained analogs. It also finds application in materials science as a precursor for liquid crystals and polymer modifiers.

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