2833-24-1
Chemical Structure
Methyl trans-4-oxo-2-pentenoate
Synonym(s): Methyl (2E)-4-oxopent-2-enoate
- CAS No.: 2833-24-1
- Formula:C6H8O3
- Molecular Weight:128.13
IUPAC Name: methyl (E)-4-oxopent-2-enoate
InChIKey: GLVNZYODMKSEPS-ONEGZZNKSA-N
SMILES: C(/C=C/C(C)=O)(OC)=O
Biological Activity: Methyl trans-4-oxo-2-pentenoate (Methyl (2E)-4-oxopent-2-enoate) is a heterofunctionalized dienophile containing both ketone and ester functional groups. The enone structure within the Methyl trans-4-oxo-2-pentenoate molecule makes it a highly reactive Michael acceptor capable of regioselective conjugate addition, which is commonly used in reactions for constructing complex ring systems such as the Robinson annulation. Methyl trans-4-oxo-2-pentenoate can serve as a substrate in the synthesis of α-(alkylmethylene) butyrolactone derivatives. Methyl trans-4-oxo-2-pentenoate participates in asymmetric Diels-Alder reactions promoted by chiral palladium complexes[1][2].
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Methyl trans-4-oxo-2-pentenoate | Methyl trans-4-oxo-2-pentenoate (Methyl (2E)-4-oxopent-2-enoate) is a heterofunctionalized dienophile containing both ketone and ester functional groups. The enone structure within the Methyl trans-4-oxo-2-pentenoate molecule makes it a highly reactive Michael acceptor capable of regioselective conjugate addition, which is commonly used in reactions for constructing complex ring systems such as the Robinson annulation. Methyl trans-4-oxo-2-pentenoate can serve as a substrate in the synthesis of α-(alkylmethylene) butyrolactone derivatives. Methyl trans-4-oxo-2-pentenoate participates in asymmetric Diels-Alder reactions promoted by chiral palladium complexes. | |||||||||||||||||||||
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References
- [1]. Leung P H, et al. Molecular recognition in the palladium complex promoted asymmetric synthesis of a keto-ester heterofunctionalized P-chiral phosphine. Tetrahedron: Asymmetry, 1998, 9(17): 2961-2964.
- [2]. Ballini R. A New Synthesis of exo-Methylene Butyrolactones from Nitroalkanes. Synthesis, 2001, 2004: 1519-1522.
