1523-68-8

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 30, p. 1265, 1965 DOI: 10.1021/jo01015a519

Upstream product

• 79-03-8 propionyl chloride 
• 122-52-1 triethyl phosphite 
• 762-04-9 Diethyl phosphonate 
• 62999-73-9 [1,3]Dithian-2-yl-phosphonic acid diethyl ester 

Downstream Products

• 122-70-3 2-phenethyl propanoate 
• 76782-67-7 Diethyl-(1-ethyl-1-hydroxy-3-phenyl-2-propinyl)phosphonat 
• 5331-64-6 1-phenyl-1,3-pentanedione 
• 42329-48-6 diethyl 1-(1-ethyl)ethenylphosphonate 
• 93-55-0 1-phenyl-propan-1-one 
• 77526-84-2 E,Z-Diethyl α-hydroxyiminopropylphosphonate 
• 76782-78-0 Diethyl-(1-ethyl-3-phenyl-1,2-propadienyl)phosphat 
• 1663-55-4 diethyl [hydroxy(phenyl)methyl]phosphonate 
• 152805-18-0 (E)-diethyl 1-benzyloxyiminopropylphosphonate 

Relevant academic research and scientific papers

Efficient catalytic asymmetric synthesis of α-substituted phenyloxyacetyloxy and aroyloxy phosphonates

Optically active α-substituted phenyloxyacetyloxy and aroyloxy phosphonates have been synthesized via catalytic asymmetric hydrogenation of the corresponding prochiral α,β-unsaturated phosphonates using Rh(I)/(R,R)-Me-DuPhos as the catalyst in methanol at

Catalytic Aldol-Cyclization Cascade of 3-Isothiocyanato Oxindoles with α-Ketophosphonates for the Enantioselective Synthesis of β-Amino-α-hydroxyphosphonates

A cascade aldol-cyclization reaction between 3-isothiocyanato oxindoles and α-ketophosphonates has been developed for the synthesis of β-amino-α-hydroxyphosphonate derivatives. Catalyzed by a quinine-based tertiary amino-thiourea derivative, this reaction

Enantioselective synthesis of quaternary α-aminophosphonates via conjugate addition of α-nitrophosphonates to enones

Enantioselective Michael addition of α-nitrophosphonates to enones for the synthesis of α-aminophosphonates is reported for the first time. The reaction proceeds in good to high yields and moderate to high selectivity in the presence of a new quinine thio

Non-hydrolysable analogues of inorganic pyrophosphate as inhibitors of hepatitis C virus RNA-dependent RNA-polymerase

Inorganic pyrophosphate (PPi) is the product of the polymerization reaction catalyzed by DNA-and RNA-polymerases. A number of novel non-hydrolsable PPi analogues was synthesized; some of them inhibited the polymerization reaction catalyzed by hepatitis C virus RNA-dependent RNA-polymerase (NS5B). A new pharmacophore based on a non-hydrolysable methylenediphosphonate backbone has been developed. The structure-activity relationship analysis of 12 bisphosphonates is presented and the structural features crucial for NS5B polymerase activity inhibition are stated. Pleiades Publishing, Ltd., 2012.

Rhodium-catalyzed enantioselective cyclizations of γ-alkynylaldehydes with acyl phosphonates: ligand- and substituent-controlled C-P or C-H bond cleavage

It has been established that a cationic rhodium(I)/(R)-H8-BINAP or (R)-Segphos complex catalyzes two modes of enantioselective cyclizations of γ-alkynylaldehydes with acyl phosphonates via C-P or C-H bond cleavage. The ligands of the Rh(I) comp

Room-temperature alternative to the arbuzov reaction: The reductive deoxygenation of Acyl phosphonates

The reductive deoxygenation of acyl phosphonates using a Wolff-Kishner-like sequence is described. This transformation allows direct access to alkyl phosphonates from acyl phosphonates at room temperature. The method can be combined with acyl phosphonate synthesis into a one pot, four-step procedure for the conversion of carboxylic acids into alkyl phosphonates. The methodology works well for a variety of aliphatic acids and shows a functional group tolerance similar to that of other hydrazone-forming reactions.

A new synthesis of α-ketophosphonates

α-Ketophosphonates are prepared from 2-alkyl-2-phosphonyl-1,3-dithianes.

Synthesis and structural properties of metal complexes of dialkyl α-hydroxyiminophosphonates

A range of dialkyl α-hydroxyiminophosphonates R'C=N(OH)P(O)(OR)2, with substituents of varying bulk (R=Et, R'=Me L1, Et L2, c-Pr L3, 3-heptyl L4; R=i-Pr, R'=Et L5, 3-heptyl L6; R=n-Bu, R'=Pr L7) have been used to synthesise neutral metal complexes with nickel(II)[Ni(L1-3,5)Cl2], cobalt(II) [Co(L1-3,5)Cl2] and lanthanides (La(III) with L1,2,5, Pr(III) with L1,2,4-7, Nd(III) with L5, Gd(III) with L2,5 and Dy(III) with L2,5) the charge being balanced by anionic ligands chloride or nitrate. Included in this range are two 3-heptyl derivatives which have not previously been reported. All the metal complexes have been fully characterised by elemental analysis, IR, electronic and NMR spectroscopy and mass spectrometry. X-Ray crystallography has been used to establish the structure of six key metal complexes and one of the free ligands (L3). Three different bonding modes have been established. The d-block metal chlorides consistently show symmetrical bidentate coordination in [ML2Cl2], the lanthanide chlorides [ML3Cl3] are all asymmetrically bidentate and monodentate coordination was observed in the neodymium nitrate complex [NdL52(NO3)3(H2O)].

Reactions of acyl tributylphosphonium chlorides and dialkyl acylphosphonates with Grignard and organolithium reagents

Ketones and esters (4) were effectively prepared by reaction of Grignard reagents with acyl tributylphosphonium chlorides (2), diethyl acylphosphonates (5), or diisopropyl acylphosphonate (6) derived from acid chlorides and chloroformates (1). Although by the method with 2, 4 is prepared in one-pot operation from 1 and generally in a higher yield, the method with 5 or 6 proved to compensate for the synthesis of 4 with 2 in some respects. The reactivities of 2, 5, and 6 as electrophiles were also evaluated by comparing their reduction potential with those of acid chlorides.

A simple synthesis of 1-aminophosphonic acids from 1-hydroxyiminophosphonates with NaBH4 in the presence of transition metal compounds

A new procedure has been developed for the synthesis of 1-aminophosphonic acids. Diethyl phosphonates are converted to hydroxyiminophosphonates when treated with hydroxylamine hydrochloride. Reduction of hydroiminophosphonates with NaBH4 in MeOH in the presence of MoO3 or NiCl2 and hydrolysis of 1-aminophosphonates gave 1-aminophosphonic acids in good yields.