Related Experiment Video
Updated: May 26, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
rac-syn-Diethyl 2-hy-droxy-4-oxo-1-phenyl-cyclo-hexane-1,2-dicarboxyl-ate
Ya-Jun Wang1, Sheng-Liang Ni, Yue Meng
1Department of Chemistry, Huzhou University, Huzhou, Zhejiang 313000, People's Republic of China.
Abstract:
The title compound, C(18)H(22)O(6), was obtained by the domino oxa-Michael-aldol (DOMA) reaction and has the cyclo-hexa-none ring in a chair conformation with intra-annular torsion angles in the range 49.9 (2)-58.9 (2)°. The two eth-oxy-carbonyl substituents on the cyclo-hexa-none ring adopt a syn configurations. In the crystal, the mol-ecules self-assemble through duplex inter-molecular hy-droxy-carbonyl O-H⋯O hydrogen bonds, giving centrosymmetric cyclic dimers [graph set R(2) (2)(12)] which inter-associate through weak C-H⋯O hydrogen-bonding inter-actions.
Related Concept Videos
Racemic Mixtures and the Resolution of Enantiomers
Disubstituted Cyclohexanes: cis-trans Isomerism
In cyclohexane, the substituents can occupy different positions generating distinct isomers.
Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.
Preparation of Epoxides
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...

