90199-67-0

Usage

Uses

Used in Pharmaceutical Synthesis:
4-OXO-HEX-5-ENOIC ACID ETHYL ESTER is used as an intermediate in the synthesis of analogs of 5-aminolevulinic acid (ALA), which are potential inhibitors of ALA dehydratase (porphobilinogen synthase), an early enzyme of tetrapyrrole biosynthesis. This application is significant in the development of drugs targeting specific metabolic pathways.
Used in the Synthesis of Bivalent Ligands for D2/D3 Dopamine Receptors:
4-OXO-HEX-5-ENOIC ACID ETHYL ESTER is an intermediate in the synthesis of 4-Oxo-6-(2-oxo-5-vinylpyrrolidin-1-yl)hexanoic Acid (O858780), which is derived from Ethyl Succinoyl Chloride (E818230). 4-OXO-HEX-5-ENOIC ACID ETHYL ESTER is used in the development of bivalent ligands for D2/D3 dopamine receptors, playing a crucial role in the treatment of neurological disorders.
Used in the Preparation of Antimicrobial Pyrrolo-Isoquinolinones:
4-OXO-HEX-5-ENOIC ACID ETHYL ESTER is also utilized in the preparation of antimicrobial pyrrolo-isoquinolinones, which are compounds with potential applications in the development of new antibiotics to combat drug-resistant bacteria.
Used in the Synthesis of Vigabatrin Impurity 2:
In the pharmaceutical industry, 4-OXO-HEX-5-ENOIC ACID ETHYL ESTER is used in the synthesis of Vigabatrin Impurity 2, which is an important aspect of drug quality control and safety assessments. This application ensures that the final drug product meets the required purity and safety standards.

Upstream product

• 411238-29-4 6-Dimethylamino-4-oxo-hexansaeure-aethylester 
• 172946-73-5 Ethyl 4-(benzotriazol-1-yl)-4-ethoxy-5-hexenoate 
• 123-76-2 levulinic acid 
• 539-74-2 Ethyl 3-bromopropionate 
• 6414-69-3 ethyl 3-iodopropanoate 
• 814-68-6 acryloyl chloride 
• 14794-31-1 ethyl 3-(chloroformyl)propionate 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 408307-66-4 6-dimethylamino-4-oxo-hexanoic acid 

Downstream Products

• 139540-29-7 (4''R)-2-<4''-(benzyloxymethyl)-hexyl>-2-(3'-iodo-propyl)-<1,3>dioxolane 
• 157733-67-0 (4''R)-3-<2'-<4''-(benzyloxymethyl)-hexyl>-<1',3'>dioxolan-2'-yl>-propan-1-ol 
• 21963-38-2 5-vinyl-dihydrofuran-2(3H)-one 

Relevant academic research and scientific papers

Enantioselective allylic hydroxylation of w-alkenoic acids and esters by P450 BM3 monooxygenase

Chiral allylic alcohols of w-alkenoic acids and derivatives thereof are highly important building blocks for the synthesis of biologically active compounds. The direct enantioselective C-H oxidation of linear terminal olefins offers the shortest route toward these compounds, but known synthetic methods are limited and suffer from low selectivities. Described herein is an enzymatic approach using the P450 BM3 monooxygenase mutant A74G/L188Q, which catalyzes allylic hydroxylation with high to excellent chemo- and enantioselectivities providing the desirable secondary alcohols.

Bioavailable affinity label for collagen prolyl 4-hydroxylase

Collagen is the most abundant protein in animals. Its prevalent 4-hydroxyproline residues contribute greatly to its conformational stability. The hydroxyl groups arise from a post-translational modification catalyzed by the nonheme iron-dependent enzyme, collagen prolyl 4-hydroxylase (P4H). Here, we report that 4-oxo-5,6-epoxyhexanoate, a mimic of the α-ketoglutarate co-substrate, inactivates human P4H. The inactivation installs a ketone functionality in P4H, providing a handle for proteomic experiments. Caenorhabditis elegans exposed to the esterified epoxy ketone displays the phenotype of a worm lacking P4H. Thus, this affinity label can be used to mediate collagen stability in an animal, as is desirable in the treatment of a variety of fibrotic diseases.

N-(α-Ethoxyallyl)benzotriazole: A Novel Propenoyl Anion Synthon Route to Vinyl Ketones

Lithiation with butyllithium of (N-(α-ethoxyallyl)benzotriazole (2) (readily prepared in quantitative yield on a large scale from benzotriazole and acrolein diethyl acetal (9)) followed by reaction of lithio derivative 14 with halides, α,β-unsaturated esters, α,β-unsaturated ketones, and aldehydes gave exclusively α-alkylation adducts.These adducts are hydrolyzed under extremely mild conditions, enabling convenient syntheses of vinyl ketones 16 and functionalized vinyl ketones 21, 22, 24, and 27.