30094-33-8

Upstream product

• 3095-95-2 diethylphosphonoacetic acid 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 7071-12-7 triethyl 2-chloro-2-phosphonoacetate 
• 3167-63-3 diethyl chloromethylphosphonate 
• 124-38-9 carbon dioxide 

Downstream Products

• 66279-60-5 (2Z,4E)-2-Chloro-5-phenyl-penta-2,4-dienoic acid 
• 705-54-4 (Z)-α-chlorocinnamic acid 
• 119288-65-2 [3-Chloro-1-(4-methoxy-phenyl)-2-oxo-4-phenyl-azetidin-3-yl]-phosphonic acid diethyl ester 
• 119288-64-1 (3-Chloro-2-oxo-1,4-diphenyl-azetidin-3-yl)-phosphonic acid diethyl ester 
• 119288-68-5 [(3S,4S)-1-(4-Methoxy-phenyl)-2-oxo-4-phenyl-azetidin-3-yl]-phosphonic acid diethyl ester 
• 119288-67-4 diethyl (+/-)-trans-1,4-diphenyl-2-oxo-azetidin-3-yl-phosphonate 
• 34255-80-6 chloro-diethoxyphosphoryl-ketene 
• 1552-72-3 (Z)-2-chloro-3-(4-methoxyphenyl)acrylic acid 

Relevant academic research and scientific papers

Discovery, Synthesis, and Biological Evaluation of Anaenamides C and D from a New Marine Cyanobacterium, Hormoscilla sp.

Our ongoing efforts to explore the chemical space associated with marine cyanobacteria from coral reefs of Guam have yielded two new members of the anaenamide family of natural products, anaenamides C (3) and D (4). These compounds were isolated from a novel Hormoscilla sp. (VPG16-58). Our phylogenetic profiling (16S rDNA) of this cyanobacterium indicated that VPG16-58 is taxonomically distinct from the previously reported producer of the anaephenes, VPG16-59 (Hormoscilla sp.), and other previously documented species of the genus Hormoscilla. The planar structures of 3 and 4 were determined via spectroscopic methods, and absolute configurations of the α-hydroxy acids were assigned by enantioselective HPLC analysis. To address the requirement for sufficient material for testing, we first adapted our published linear synthetic approach for 1 and 2 to generate anaenoic acid (7), which served as a point for diversification, providing the primary amides 3 and 4 from synthetic intermediates 5 and 6, respectively. The compounds were then tested for effects on HCT116 colon cancer cell viability and in an ARE-luciferase reporter gene assay for Nrf2 modulation using HEK293 human embryonic kidney cells. Our findings indicate that, in contrast to cytotoxic methyl esters 1 and 2, the primary amides 3 and 4 activate the Nrf2 pathway at noncytotoxic concentrations. Overall, our data suggest that the anaenamide scaffold is tunable to produce differential biological outcomes.

A new general approach to 4-substituted-3-halo-2-quinolones

A general procedure for the preparation of 4-substituted-3-halo-2-quinolones (halo = F, Cl, Br) utilizing 2-halo diethylphosphonoacetic acids (halo = F, Cl, Br) and o-aminophenylketones as the starting materials is described. The title compounds are obtained by an intramolecular Horner-Wadsworth-Emmons olefination of halogen-containing N-acyl-o-aminophenylketones. The transformation process is generally applicable under mild conditions.

A useful synthesis of diethyl 1-substituted vinylphosphonates

A variety of diethyl 1-substituted vinylphosphonates 8 has been conveniently synthesized by piperidine catalyzed decarboxylative condensation of 2-diethoxyphosphorylalkanoic acids and 2-diethoxyphosphorylalkenoic acids 7 with formaldehyde.

Cycloaddition Reactions of (Diethylphosphono)ketenes

Methyl- and chloro(diethylphosphono)ketenes were found to add to cyclopentadiene or imines in unusual manner in the certain cases.Some chemical conversions and the Horner-Wittig reaction of the cycloadducts were examined.

A Facile and General, One-pot Synthesis of 2-Oxoalkane Phosphonates from Diethylphosphonocarboxylic Acid Chlorides and Organometallic Reagents

An efficient and general method for the preparation of 2-oxoalkane phosphonates 2 is described.Diethylphosphono-2-alkanoyl chlorides are used to introduce directly the 2-oxophosphonate 1-substituted synthons on Grignard or cuprate reagents.