89590-29-4

Basic information

• Product Name: 2-Butenedioic acid, 2-cyclohexyl-, dimethyl ester, (Z)-
• CAS NO: 89590-29-4
• Molecular Formula: C12H18O4
• Molecular Weight: 226.273
• Mol File: 89590-29-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-Butenedioic acid, 2-cyclohexyl-, dimethyl ester, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butenedioic acid, 2-cyclohexyl-, dimethyl ester, (Z)-(89590-29-4)
• EPA Substance Registry System: 2-Butenedioic acid, 2-cyclohexyl-, dimethyl ester, (Z)-(89590-29-4)

Safety Data

• Hazardous Substances Data: 89590-29-4(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 931-48-6 2-cyclohexylacetylene 
• 201230-82-2 carbon monoxide 
• 931-51-1 cyclohexylmagnesiumchloride 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 110-82-7 cyclohexane 

Relevant articles and documents

Asymmetric hydrogenation of maleic acid diesters and anhydrides

Asymmetric hydrogenation of maleic and fumaric acid derivatives with iridium catalysts based on N,P ligands provides an efficient route to chiral enantioenriched succinates. A new catalyst derived from a 2,6-difluorophenyl- substituted pyridine-phosphinite ligand was developed and enables the conversion of a wide range of 2-alkyl and 2-arylmaleic acid diesters into the corresponding succinates in high enantiomeric purity. Mixtures of cis/trans substrates can be hydrogenated in an enantioconvergent fashion with high enantioselectivity, and further enhances the scope of this transformation. The products are valuable chiral building blocks with a structural motif found in many bioactive compounds, such as metalloproteinase inhibitors. An attractive enantioselective route to 2-alkyl- and 2-aryl-substituted succinic acid derivatives is opened up by the asymmetric hydrogenation of maleic and fumaric acid derivatives, using the new catalyst [Ir(cod)L]BArF, derived from a 2,6-difluorophenyl-substituted pyridine-phosphinite ligand. The products are valuable chiral building blocks having a structural motif found in many bioactive compounds. cod=1,5-cyclooctadiene.

SELECTIVE HYDROESTERIFICATION OF ALKYNES TO MONO- OR DIESTERS

Terminal alkynes (including acetylene) undergo regioselective hydroesterification to unsaturated cis-diesters using PdCl2, CuCl2, HCl, alcohol, carbon monoxide, and oxygen; cis-monoesters are formed from internal alkynes.These reactions are complete within two hours at room temperature and atmospheric pressure.