3675-31-8

Basic information

• Product Name: cyclohex-2-en-1-ylacetic acid
• CAS NO: 3675-31-8
• Molecular Formula: C₈H₁₂O₂
• Molecular Weight: 140.1797
• Mol File: 3675-31-8.mol

Chemical Properties

• Boiling Point: 262.9°C at 760 mmHg
• Flash Point: 160.2°C
• Density: 1.062g/cm³
• Vapor Pressure: 0.00312mmHg at 25°C
• Refractive Index: 1.49
• CAS DataBase Reference: cyclohex-2-en-1-ylacetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: cyclohex-2-en-1-ylacetic acid(3675-31-8)
• EPA Substance Registry System: cyclohex-2-en-1-ylacetic acid(3675-31-8)

Safety Data

• Hazardous Substances Data: 3675-31-8(Hazardous Substances Data)

Upstream product

• 2138-99-0 cyclohex-2-enyl-malonic acid 
• 19656-95-2 2-cyclohexenylacetaldehyde 
• 21331-58-8 ethyl (cyclohexen-3-yl)acetate 
• 21448-77-1 (1α,6α,7α)-bicyclo[4.1.0]heptane-7-carboxylic acid 
• 64-19-7 acetic acid 
• 1521-51-3 rac-3-bromocyclohexene 
• 88850-07-1 C₁₅H₁₈Cl₂O₃Te 
• 78-39-7 Triethyl orthoacetate 
• 822-67-3 Cyclohex-2-enol 
• 110-86-1 pyridine 
• 54486-97-4 5α-iodo-1α,6α-7-oxabicyclo <4,3,0> nonan-8-one 
• 34939-28-1 dimethyl 2-(cyclohex-2-en-1-yl)malonate 
• 6305-63-1 diethyl 2-(cyclohex-2-enyl)malonate 
• 110-83-8 cyclohexene 

Downstream Products

• 111293-38-0 6-chloro-3-cyclohex-2-enylmethyl-1,1-dioxo-1,2(4)-dihydro-1λ⁶-benzo[1,2,4]thiadiazine-7-sulfonic acid amide 
• 54385-27-2 N-Methyl-2-(2-cyclohexen-1-yl)-acetamid 
• 65291-16-9 (3aα,7α,7aα)-hexahydro-7-(phenylseleno)-2(3H)-benzofuranone 
• 88850-07-1 C₁₅H₁₈Cl₂O₃Te 
• 82725-66-4 <1,1-(2)H2>-2-(3-Cyclohexenyl)ethanol 
• 112052-21-8 methyl 2-(cyclohex-2-en-1-yl)acetate 
• 71404-68-7 7-oxa-8-oxo-thiophenylbicyclo<4.3.0>nonane 
• 18955-93-6 1-(2'-cyclohexenyl)-2-propanone 
• 158233-84-2 1-Cyclohex-2-enyl-5-methylhexan-2-one 
• 197148-65-5 Cyclohex-2-enyl-acetic acid 2-thioxo-2H-pyridin-1-yl ester 
• 124803-84-5 isobutylamide of cyclohex-2-ene acetic acid 
• 16452-34-9 2-(cyclohex-2-enyl)ethanol 
• 20390-71-0 2-hydroxy-3-cyclohexen-1-acetic acid lactone 
• 34905-87-8 3a,4,7,7a-tetrahydro-1-benzofuran-2(3H)-one 

Relevant articles and documents

Bidentate auxiliary-directed alkenyl C-H allylation: Via exo-palladacycles: Synthesis of branched 1,4-dienes

An alkenyl C-H allylation by an exo-palladacycle intermediate is demonstrated, employing unactivated (Z)-Alkenes and allyl carbonates. With the use of an 8-Aminoquinoline (AQ) derived amide as the directing group, the N,N-bidentate-chelation-Assisted C-H activation protocol proceeded under mild and oxidant-free conditions with excellent selectivity. The utility of this approach is demonstrated by the preparative scale, selective conversion of inseparable Z/E alkenes and ready removal of the amide auxiliary to provide the corresponding ester.

Pyrrolidines and Piperidines by Ligand-Enabled Aza-Heck Cyclizations and Cascades of N-(Pentafluorobenzoyloxy)carbamates

Ligand-enabled aza-Heck cyclizations and cascades of N-(pentafluorobenzoyloxy)carbamates are described. These studies encompass the first examples of efficient non-biased 6-exo aza-Heck cyclizations. The methodology provides direct and flexible access to carbamate protected pyrrolidines and piperidines.

Rapid Access to Thiolactone Derivatives through Radical-Mediated Acyl Thiol-Ene and Acyl Thiol-Yne Cyclization

A new synthetic approach to thiolactones that employs an efficient acyl thiol-ene (ATE) or acyl thiol-yne (ATY) cyclization to convert unsaturated thiocarboxylic acid derivatives into thiolactones under very mild conditions is described. The high overall yields, fast kinetics, high diastereoselectivity, excellent regiocontrol, and broad substrate scope of these reaction processes render this a very useful approach for diversity-oriented synthesis and drug discovery efforts. A detailed computational rationale is provided for the observed regiocontrol.

Synthesis of β-Keto Lactone with Basic Skeleton of Przewalskin B

The synthesis of β-keto lactone was completed using cyclohexanone as starting material. The α,β-unsaturated lactone was obtained through Reformatsky reaction and iodolactonization. The aforementioned lactone was converted into target compound 1 (β-keto lactone) by Nef oxidation and Claisen condensation in six steps with 17.9% overall yield.

Synthesis of Secondary Unsaturated Lactams via an Aza-Heck Reaction

The preparation of unsaturated secondary lactams via the palladium-catalyzed cyclization of O-phenyl hydroxamates onto a pendent alkene is reported. This method provides rapid access to a broad range of lactams that are widely useful building blocks in alkaloid synthesis. Mechanistic studies support an aza-Heck-type pathway.

Diverse N-Heterocyclic Ring Systems via Aza-Heck Cyclizations of N-(Pentafluorobenzoyloxy)sulfonamides

Aza-Heck cyclizations initiated by oxidative addition of Pd0-catalysts into the N?O bond of N-(pentafluoro-benzoyloxy)sulfonamides are described. These studies, which encompass only the second class of aza-Heck reaction developed to date, provide direct access to diverse N-heterocyclic ring systems.

Oxidative cyclizations in a nonpolar solvent using molecular oxygen and studies on the stereochemistry of oxypalladation

Oxidative cyclizations of a variety of heteroatom nucleophiles onto unactivated olefins are catalyzed by palladium(II) and pyridine in the presence of molecular oxygen as the sole stoichiometric oxidant in a nonpolar solvent (toluene). Reactivity studies of a number of N-ligated palladium complexes show that chelating ligands slow the reaction. Nearly identical conditions are applicable to five different types of nucleophiles: phenols, primary alcohols, carboxylic acids, a vinylogous acid, and amides. Electronrich phenols are excellent substrates, and multiple olefin substitution patterns are tolerated. Primary alcohols undergo oxidative cyclization without significant oxidation to the aldehyde, a fact that illustrates the range of reactivity available from various Pd(II) salts under differing conditions. Alcohols can form both fused and spirocyclic ring systems, depending on the position of the olefin relative to the tethered alcohol; the same is true of the acid derivatives. The racemic conditions served as a platform for the development of an enantioselective reaction. Experiments with stereospecifically deuterated primary alcohol substrates rule out a "Wacker-type" mechanism involving anti oxypalladation and suggest that the reaction proceeds by syn oxypalladation for both mono- and bidentate ligands. In contrast, cyclizations of deuterium-labeled carboxylic acid substrates undergo anti oxypalladation.

Inversion of the direction of stereoinduction in the coupling of chiral γ,δ-unsaturated fischer carbene complexes with o-ethynylbenzaldehyde

(matrix presented) A variety of γ,δ-unsaturated carbene complexes that feature a stereogenic center at the β-carbon couple with 2-ethynylbenzaldehyde to afford hydrophenanthrene derivatives with a high degree of stereoinduction. The direction of stereoinduction is opposite for examples where the stereogenic center is acyclic vs examples where it is within a ring.

Ketone-directed peracid epoxidation of cyclic alkenes

Ketone carbonyl groups are shown to direct the peracid epoxidation of cyclic alkenes with greater selectivity than that displayed by esters. An 18O labelling study is used to show that a dioxirane intermediate is not involved in these reactions.

Ketone-directed peracid epoxidation

Ketone carbonyl groups are shown to direct the epoxidation of cyclic alkenes with higher selectivity than that displayed by esters. An 18O labelling study is used to show that a dioxirane intermediate is not involved in these reactions.