67201-29-0

Usage

Physical state

Colorless to pale yellow liquid

Odor

Fruity, herbaceous

Uses

a. Fragrance ingredient in perfumes and personal care products
b. Intermediate in the synthesis of other organic compounds
c. Flavoring agent in the food industry
d. Building block for the synthesis of active ingredients in pharmaceuticals and agrochemicals

Appearance

Colorless to pale yellow liquid

Application

Widely used in the perfume, personal care, food, pharmaceutical, and agrochemical industries

Chemical structure

Contains a cyclohexene ring with a carboxylic acid group, an ester group, and a ketone group

Solubility

Soluble in organic solvents like ethanol, acetone, and diethyl ether

Stability

Stable under normal temperature and pressure conditions, but may decompose upon exposure to heat, light, or strong acids and bases

Upstream product

• 54125-02-9 danishefsky's diene 
• 292638-85-8 acrylic acid methyl ester 
• 208928-20-5 methyl 2-methoxy-4-[(trimethylsilyl)oxy]cyclohex-3-ene-1-carboxylate 
• 943442-63-5 4-carbomethoxy-3-dimethylamino-1-tert-butyldimethylsiloxy-1-cyclohexene 
• 38053-91-7 2-trimethylsilyloxy-1,3-butadiene 
• 922-67-8 propynoic acid methyl ester 
• 137033-10-4 4-(tert-Butyl-dimethyl-silanyloxy)-3-p-tolylsulfanyl-cyclohex-3-enecarboxylic acid methyl ester 
• 77611-97-3 7-Oxabicyclo<4.1.0>hept-4-en-4-carbonsaeure-methylester 
• 137033-05-7 3-(p-tolylthio)-2-(trimethylsilyloxy)-1,3-butadiene 
• 91281-50-4 2-tert-Butoxy-4-trimethylsilanyloxy-cyclohex-3-enecarboxylic acid methyl ester 
• 67201-23-4 methyl 2-trimethylsilyl-4-trimethylsilyloxycyclohex-3-enecarboxylate 
• 54584-38-2 methyl 1,4-dioxaspiro<4,5>dec-7-ene-8-carboxylate 

Relevant academic research and scientific papers

Pd-catalyzed stereospecific azide substitution of α,β- unsaturated γ,δ-epoxy esters with double inversion of configuration

(Chemical Equation Presented) Acyclic, cyclic, and optically active unsaturated γ,δ-epoxy esters are employed in a highly stereoselective synthesis of functionalized amino alcohols, amino acids, and α,α-disubstituted amino acids. The key step of the react

PYRROLO[2,3-B]PYRIDINE CDK9 KINASE INHIBITORS

Disclosed are compounds of Formula (IIa), wherein R1, R2, R3A, R3B, R3C, R3D, R3E, and R4 are as defined in the specification, and pharmaceutically acceptable salts thereof. The compounds may be used as agents in the treatment of diseases, including cancer. Also provided are pharmaceutical compositions comprising one or more compounds of Formula (IIa)

Synthesis of 3,4-fused cycloalkanopyrroles by 1,3-dipolar cycloaddition

The synthesis of a number of 3,4-fused cycloalkanopyrroles bearing substituents on the cycloalkane ring was accomplished by 1,3-dipolar cycloaddition. The yield of the cyclization appeared to depend on the base-sensitivity of the Michael acceptor, but the method is applicable across a broad range of cyclic α,β-unsaturated ketone esters. Functional group transformations can be undertaken following pyrrole synthesis to increase the diversity of cycloalkanopyrroles accessible by this method. One pyrrole thus made is a diester of a conformationally-constrained analogue of porphobilinogen, the precursor of the natural tetrapyrroles.

A new one-pot synthetic approach to the highly functionalized (Z)-2-(buta-1,3-dienyl)phenols and 2-methyl-2H-chromenes: Use of amine, ruthenium and base-catalysis

A practical and simple one-pot multi-catalysis process for the synthesis of highly substituted benzo[b]oxepines 5, (Z)-2-(buta-1,3-dienyl)phenols 6 and 2-methyl-2H-chromenes 7 from simple starting materials was achieved for the first time through ring-closing metathesis/base-induced ring opening/[1,7]-sigmatropic hydrogen shift reactions. The synthesis of privileged (Z)-2-(buta-1,3-dienyl)phenols 6 via base-induced ring opening of highly functionalized benzo[b]oxepines 5 is described. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Aminodeoxychorismate synthase inhibitors from one-bead one-compound combinatorial libraries: "Staged" inhibitor design

4-Amino-4-deoxychorismate synthase (ADCS) catalyzes the first step in the conversion of chorismate into p-aminobenzoate, which is incorporated into folic acid. We aim to discover compounds that inhibit ADCS and serve as leads for a new class of antimicrobial compounds. This report presents (1) synthesis of a mass-tag encoded library based on a "staged" design, (2) massively parallel fluorescence-based on-bead screening, (3) rapid structural identification of hits, and (4) full kinetic analysis of ADCS. All inhibitors are competitive against chorismate and Mg2+. The most potent ADCS inhibitor identified has a Ki of 360 μM. We show that the combinatorial diversity elements add substantial binding affinity by interacting with residues outside of but proximal to the active site. The methods presented here constitute a paradigm for inhibitor discovery through active site targeting, enabled by rapid library synthesis, facile massively parallel screening, and straightforward hit identification.

Synthesis of 4-aminocyclohex-1-enecarboxylates from Danishefsky's diene

An efficient BF3·Et2O mediated conversion of Diels-Alder adduct 1 of Danishefsky's diene and methyl acrylate yielded cyclohexenones 2 and 3. Subsequent reductive amination with several amines using NaBH(OAc)3 in acetic acid medium gave 4-alkylaminocyclohex-1-enecarboxylate derivatives (4a-e) in a concise form.

An improved synthesis of 4-methylene-2-cyclohexen-1-one

An improved synthesis of 4-methylene-2-cyclohexen-1-one (1) is described, which involves four steps from commercially available starting materials and proceeds in 65-75% overall yield.

Simple Synthesis and the Diels-Alder Reaction of 3-(p-Tolylthio)-2-(trimethylsilyloxy)-1,3-butadiene

The reaction of 3-(p-tolylsulfinyl)-2-butanone with trimethylsilyl trifluoromethanesulfonate in the presence of diisopropylethylamine gave 3-(p-tolylthio)-2-(trimethylsilyloxy)-1,3-butadiene (2) quantitatively.The Diels-Alder reactions of 2 and the relate