637000-43-2

Basic information

• Product Name: 3-Cyclohexene-1-carboxylicacid,3-methyl-,methylester,(1S)-(9CI)
• Synonyms: 3-Cyclohexene-1-carboxylicacid,3-methyl-,methylester,(1S)-(9CI)
• CAS NO: 637000-43-2
• Molecular Formula: C9H14O2
• Molecular Weight: 154.21
• Product Categories: CARBOXYLICESTER
• Mol File: 637000-43-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Cyclohexene-1-carboxylicacid,3-methyl-,methylester,(1S)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyclohexene-1-carboxylicacid,3-methyl-,methylester,(1S)-(9CI)(637000-43-2)
• EPA Substance Registry System: 3-Cyclohexene-1-carboxylicacid,3-methyl-,methylester,(1S)-(9CI)(637000-43-2)

Safety Data

• Hazardous Substances Data: 637000-43-2(Hazardous Substances Data)

Upstream product

• 292638-85-8 acrylic acid methyl ester 
• 78-79-5 isoprene 
• 67-56-1 methanol 
• 54385-25-0 (+/-)-3-methylcyclohex-3-ene-1-carboxylic acid 
• 814-68-6 acryloyl chloride 
• 93604-50-3 3-Methyl-4-phenylsulfanyl-cyclohex-3-enecarboxylic acid methyl ester 
• 56980-32-6 3-methyl-3-cyclohexene-1-carbonylaldehyde 
• 209546-62-3 (E)-3-Phenylselanylcarbonyl-acrylic acid methyl ester 

Relevant articles and documents

Polyelectrolyte-catalyzed Diels–Alder reactions

Imidazolium-based poly(ionic liquids) bearing bromide and bis(trifluoromethane)sulfonimide as counteranions [poly(ViEIm)Br and poly(ViEIm)NTf2] derived from reversible addition fragmentation chain transfer (RAFT) polymerization techniques are u

Silica-supported chlorometallate(iii) ionic liquids as recyclable catalysts for Diels-Alder reaction under solventless conditions

A range of Lewis acidic metal chlorides were tested as homogeneous catalysts in a model Diels-Alder reaction; AlCl3and GaCl3performed best in terms of conversion andendo : exoselectivity. Based on this outcome, the corresponding chlorometallate(iii) ionic liquids were tested as homogeneous catalysts, without a decrease in performance compared to the chlorides. Finally, these ionic liquids were heterogenised by covalent tethering of the cation onto a multimodal porous silica support; such supported chlorogallate(iii) ionic liquids are reported for the first time. Supported chlorometallate(iii) ionic liquids were used as recyclable heterogeneous catalysts for the Diels-Alder reaction under solventless conditions. High yields (99%) and highendo-selectivities (95%) were obtained after very short reaction times (5 min) at near-ambient temperature (25 °C).

Diels-alder reaction between isoprene and methyl acrylate over different zeolites: Influence of pore topology and acidity

The Diels-Alder reaction between isoprene and methyl acrylate over several zeolites was thoroughly investigated. ZSM-5 zeolites provided the highest productivity in methyl 4-methylcyclohex-3-enecarboxylate isomer, achieving 0.219mmol product per mmolHsup

Impact of carbon dioxide pressurization on liquid phase organic reactions: A case study on Heck and Diels-Alder reactions

Heck coupling reactions of methyl acrylate with various aryl bromides have been investigated using a Pd/TPP catalyst in toluene under pressurized CO 2 conditions up to 13 MPa. Although CO2 is not a reactant, the pressurization of the reaction liquid phase with CO2 has positive and negative impacts on the rate of Heck coupling depending on the structures of the substrates examined. In the case of either 2-bromoacetophenone or 2-bromocinnamate, the conversion has a maximum at a CO2 pressure of about 3 MPa; for the former, it is much larger by a factor of 3 compared with that under ambient pressure. For 2-bromobenzene, in contrast, the conversion is minimized at a similar CO2 pressure, being half compared with that at ambient pressure. In the other substrates, including the other isomers of these three aryl bromides, the conversion simply decreases or does not change so much with the CO2 pressure. To examine the factors responsible for the effects of CO2 pressurization, the phase behavior and the molecular interactions with dense phase CO2 have also been studied by visual observation and in situ high pressure FT-IR spectroscopy. In addition, impact of CO2 pressurization was also studied for the Diels-Alder reactions of isoprene with a few dienophiles like methyl acrylate, methyl vinyl ketone, and acrolein in the same solvent, toluene, but a heterogeneous silica-alumina catalyst was used (the reaction system was liquid-solid biphasic). When the CO2 pressure is raised, the conversion monotonously decreases for the three dienophiles; however, the product selectivity changes with the pressure, in particular for acrolein. The FT-IR spectroscopic measurements suggest that its reactivity is altered by interactions with CO2 molecules under pressurized conditions.

Fructose-derived ionic liquids: Recyclable homogeneous supports

A new homogeneous support has been developed that is based on a fructose-derived ionic liquid. It has been applied to the preparation of a series of supported Diels-Alder adducts. The cleavage of these adducts from the ionic liquid has resulted in some interesting observations regarding the base stability of imidazolium cations. Using a transesterification cleavage, the ionic support can be recovered and recycled.

High-pressure effect on organic reactions in fluorophobic media

The kinetic effect of fluorophobic interactions was examined in Diels-Alder reactions and the conjugate addition of amines to acrylonitrile at different pressures. Its magnitude is lower than for other solvophobic media (water, ethylene glycol). Activatio

Nanoporous solid acid catalyst for the Diels-Alder reaction of 1,3-dienes with acrylates

Nanoporous aluminosilicate, Al-HMS with a high aluminum content, strong acidity, and nanoporosity was found to catalyze the Diels-Alder reaction of 1,3-dienes with methacrylate and acrylate, and turned out to be a green alternative to homogeneous acid catalysts.

Phosphonium tosylates as solvents for the Diels-Alder reaction

Phosphonium tosylates have been investigated as solvents for the Diels-Alder reactions of isoprene with methyl acrylate, but-3-en-2-one and acrylonitrile. The reactions with oxygen-containing dienophiles showed high regioselectivity.

Silica-Promoted Diels-Alder Reactions in Carbon Dioxide from Gaseous to Supercritical Conditions

Amorphous fumed silica (SiO2) was shown to increase yields and selectivities of several Diels-Alder reactions in gaseous and supercritical CO2. Pressure effects on the Diels-Alder reaction were explored using methyl vinyl ketone and penta-1,3-diene at 80°C. The selectivity of the reaction was not affected by pressure/ density. As pressure was increased, the yield decreased. At the reaction temperature, adsorption isotherms at various pressures were obtained for the reactants and the Diels-Alder adduct. As expected when pressure is increased, the ratio of the amount of reactants adsorbed to the amount of reactants in the fluid phase decreases, thus causing the yield to decrease. The Langmuir adsorption model fit the adsorption data. The Langmuir equilibrium partitioning constants all decreased with increasing pressure. The effect of temperature on adsorption was experimentally determined and traditional heats of adsorption were calculated. However, since supercritical CO2 is a highly compressible fluid, it is logical to examine the effect of temperature at constant density. In this case, entropies of adsorption were obtained. The thermodynamic properties that influence the real enthalpy and entropy of adsorption were derived. Methods of doping the silica and improving yields and selectivities were also explored.

Diels-Alder reactions of α,β-unsaturated thioesters and α,β-unsaturated selenoesters

α,β-Unsaturated thioesters and selenoesters serve as dienophiles in Diels-Alder reactions with a variety of 1,3-dienes. Good levels of regioselectivity are obtained with unsymmetrical dienes when Lewis acid promoters are used. Thioesters and selenoesters