39758-40-2

Basic information

• Product Name: Phosphonic acid, [2-(4-fluorophenyl)-2-oxoethyl]-, diethyl ester
• CAS NO: 39758-40-2
• Molecular Formula: C12H16FO4P
• Molecular Weight: 274.229
• Mol File: 39758-40-2.mol
• Article Data: 25

Chemical Properties

• CAS DataBase Reference: Phosphonic acid, [2-(4-fluorophenyl)-2-oxoethyl]-, diethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Phosphonic acid, [2-(4-fluorophenyl)-2-oxoethyl]-, diethyl ester(39758-40-2)
• EPA Substance Registry System: Phosphonic acid, [2-(4-fluorophenyl)-2-oxoethyl]-, diethyl ester(39758-40-2)

Safety Data

• Hazardous Substances Data: 39758-40-2(Hazardous Substances Data)

Upstream product

• 683-08-9 Diethyl methylphosphonate 
• 403-43-0 4-fluorobenzoyl chloride 
• 766-98-3 1-ethynyl-4-fluorobenzene 
• 762-04-9 phosphonic acid diethyl ester 
• 403-33-8 methyl 4-flurobenzoate 
• 75175-77-8 3-(dimethylamino)-1-(4-fluorophenyl)prop-2-en-1-one 
• 29681-98-9 p-fluorobenzoylacetone 
• 459-32-5 4-fluorocinnamic acid 
• 405-99-2 para-fluorostyrene 
• 102692-35-3 4,4'-difluorochalcone 
• 399-10-0 4'-fluorochalcone 
• 451-46-7 4-fluorobenzoic acid ethyl ester 
• 24393-50-8 ethyl 4-fluorocinnamate 
• 403-29-2 2-bromo-4'-fluoroacetophenone 

Downstream Products

• 1451191-61-9 C₁₅H₂₁FNO₃P 
• 1451191-73-3 C₁₅H₂₁FNO₃P 
• 1451191-75-5 C₁₅H₂₁FNO₃P 
• 1441045-96-0 diethyl (1-chloro-2-(4-fluorophenyl)-2-oxoethyl)phosphonate 

Relevant articles and documents

Copper-Catalyzed Microwave-Expedited Oxyphosphorylation of Alkynes with Diethyl Phosphite and t-Butyl Hydroperoxide Synthesis of Densely Functionalized Phosphonylated Indenones

Treatment of alkynes with diethyl phosphite and t-butyl hydroperoxide in the presence of [Cu(MeCN)4]BF4 under microwave irradiation produced the oxyphosphorylation of the triple bond, giving rise to the corresponding β-ketophosphonates in moderate-to-good yields. When the triple bond was conjugated to a carbonyl group bearing an aromatic ring, it led to the cyclization of the resulting ketone intermediate, producing eventually different phosphonylated indenones.

Access to chiral α-substituted-β-hydroxy arylphosphonates enabled by biocatalytic dynamic reductive kinetic resolution

Ketoreductase (KRED)-catalyzed dynamic reductive kinetic resolution (DYRKR) of α-substituted-β-keto arylphosphonates was developed as a generic and stereoselective approach to synthesize chiral α-substituted-β-hydroxy arylphosphonates, with moderate-to-excellent isolated yield (up to 96%), good-to-excellent diastereoselectivity (up to >99 : 99% ee) being achieved.

Synthesis and antiproliferative evaluation of new zampanolide mimics

(?)-Zampanolide is a marine microtubule-stabilizing macrolide that has been shown by in vitro experiments to be a promising anticancer lead compound. Through its unique covalent-binding with β-tubulin, zampanolide exhibits cytotoxic potency towards multi-drug resistant cancer cells that is superior to paclitaxel. However, the limited availability of zampanolide impedes its further in vivo evaluation as a viable drug candidate. Zampanolide is envisioned to become more drug-like if its chemically fragile side chain can be stabilized; hence, this project aims to develop mimics of zampanolide with a stable side chain using straightforward synthetic methods. To this end, twelve novel zampanolide mimics (51-62) with conjugated and planar side chains have been synthesized via a 24-step sequence for each mimic from commercially available 2-butyn-1-ol as starting material. A Horner-Wadsworth-Emmons reaction incorporates the α,β-unsaturated ketone side chain and also closes the core macrocycle. WST-1 cell proliferation assays in three docetaxel-sensitive and two docetaxel-resistant human prostate cancer cell models confirm that a suitably designed side chain can serve as a bioisostere for the N-acyl hemiaminal side chain in zampanolide. Mimic 52 with a 17R chiral center was identified as the optimal candidate with IC50 values of 0.29-0.46 μM against both docetaxel-sensitive (PC-3 and DU145) and docetaxel-resistant prostate cancer cell lines (PC-3/DTX and DU145/DTX). Zampanolide mimic 52 exhibited equivalent antiproliferative potency towards both docetaxel-sensitive and docetaxel-resistant cell lines, with relative resistance in the range of 0.9-1.6.