13504-37-5

Upstream product

• 18855-51-1 Diaethyl-<α-dimethylamino-styryl>-phosphonat 
• 103-80-0 phenylacetyl chloride 
• 122-52-1 triethyl phosphite 
• 100-52-7 benzaldehyde 
• 103-82-2 phenylacetic acid 
• 18855-52-2 tetraethyl dimethylaminomethylenediphosphonate 
• 62999-73-9 [1,3]Dithian-2-yl-phosphonic acid diethyl ester 

Downstream Products

• 37127-99-4 2-benzyl-4,5-dimethyl-4H-[1,4]thiazin-3-one 
• 30015-72-6 2,4-dibenzyl-2H-benzo[b][1,4]thiazin-3(4H)-one 
• 57180-20-8 C₂₂H₂₇N₂O₅P 
• 141543-06-8 (1-Hydroxy-1-nitromethyl-2-phenyl-ethyl)-phosphonic acid diethyl ester 
• 77526-86-4 {1-[(E)-Hydroxyimino]-2-phenyl-ethyl}-phosphonic acid diethyl ester 
• 93544-95-7 Bromphenylacetylphosphonsaeure-diethylester 
• 762-04-9 phosphonic acid diethyl ester 
• 937-39-3 2-phenylacetylhydrazine 
• 98732-86-6 Z-1-Benzyliden-3-oxobutyl-phosphonsaeure-diethylester 
• 98732-85-5 (E)-2-(diethoxyphosphinyl)-3-phenylprop-2-enyl methyl ketone 
• 173848-00-5 (1-Hydrazono-2-phenyl-ethyl)-phosphonic acid diethyl ester 
• 243137-81-7 1,1,2,2,3,3,4,4,4-Nonafluoro-butane-1-sulfonic acid (E)-1-(diethoxy-phosphoryl)-2-phenyl-vinyl ester 
• 10264-08-1 N-cyclohexyl-2-phenyl-acetamide 
• 10264-09-2 N-butyl-2-phenylacetamide 

Relevant academic research and scientific papers

A new synthesis of α-ketophosphonates

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

Diazophosphonates: Effective Surrogates for Diazoalkanes in Pyrazole Synthesis

Diazophosphonates, readily prepared from α-ketophosphonates by oxidation of the corresponding hydrazones in batch or in flow, are useful partners in 1,3-dipolar cycloaddition reactions to alkynes to give N-H pyrazoles, including the first intramolecular examples of such a process. The phosphoryl group imbues a number of desirable properties into the diazo 1,3-dipole. The electron-withdrawing nature of the phosphoryl stabilizes the diazo compound making it easier to handle, whilst the ability of the phosphoryl group to migrate readily in a [1,5]-sigmatropic rearrangement enables its transfer from C to N to aromatize the initial cycloadduct, and hence its facile removal from the final pyrazole product. Overall, the diazophosphonate acts as a surrogate for the much less stable diazoalkane in cycloadditions, with the phosphoryl group playing a vital, but traceless, role. The cycloaddition proceeds more readily with alkynes bearing electron-withdrawing groups, and is regiospecific with asymmetrical alkynes. The potential of diazophosphonates for use in bioorthogonal cycloadditions is demonstrated by their facile addition to strained alkynes.

Phosphonic acid analogs of fluorophenylalanines as inhibitors of human and porcine aminopeptidases N: Validation of the importance of the substitution of the aromatic ring

A library of phosphonic acid analogs of phenylalanine substituted with fluorine, chlorine and trifluoromethyl moieties on the aromatic ring was synthesized and evaluated for inhibitory activity against human (hAPN) and porcine (pAPN) aminopeptidases. Fluorogenic screening indicated that these analogs are micromolar or submicromolar inhibitors, both enzymes being more active against hAPN. In order to better understand the mode of the action of the most active compounds, molecular modeling was used. It confirmed that aminophosphonic portion of the enzyme is bound nearly identically in the case of all the studied compounds, whereas the difference in activity results from the placement of aromatic side chain of an inhibitor. Interestingly, both enantiomers of the individual compounds are usually bound quite similarly.

First Synthesis of (R)- and (S)-1,2,3,4-Tetrahydroisoquinoline-3-phosphonic Acid (TicP) Using a Pictet-Spengler Reaction

We report here a practical and efficient synthesis of diethyl 1,2,3,4-tetrahydroisoquinoline-3-phosphonate derivatives. The target compounds were prepared in good yield using a Pictet-Spengler reaction involving α-amino phosphonates that were easily obtai

Potassium N-iodo p-toluenesulfonamide (TsNIK, iodamine-T): A new reagent for the oxidation of hydrazones to diazo compounds

A new reagent for the oxidation of hydrazones to diazo compounds is described. N-Iodo p-toluenesulfonamide (TsNIK, iodamine-T) allows the preparation of α-diazoesters, α-diazoamides, α-diazoketones and α-diazophosphonates in good yield and in high purity after a simple extractive work-up. α-Diazoesters were also obtained in high yield from the corresponding ketones through a one-pot process of hydrazone formation/oxidation. Diazo compounds: N-Iodo p-toluenesulfonamide (TsNIK, iodamine-T), readily prepared from p-toluenesulfonamide and iodine in aqueous KOH, is a new reagent for the oxidation of hydrazones to diazo compounds in good yields and high purity (see scheme).

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

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.

Synthesis of some α-ketophosphonates comprising mobile hydrogens in position α: Spectroscopic characteristics of 1H, 13C, 31P NMR and IR reactivities among amines and hydrazine derivatives

In the present work we describe the keto-enol equilibrium of some acylphosphonates 1 by means of 1H, 13C, 31P NMR, and IR data which show that the enol form has E configuration. The keto/enol ratio is determined on the basis of 31P NMR data. The reactivity of 1 with hydrazines derivatives and primary amines are reported. The structure of all compounds is determined by 1H, 13C, 31P NMR, and IR.

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.

STUDIES ON ORGANOPHOSPHORUS COMPOUNDS. 94. SYNTHESES OF 1-HYDRAZINO- AND 2-HYDRAZINO-ALKYLPHOSPHONIC ACIDS AND DERIVATIVES THEREOF

A series of 1-hydrazino- and 2-hydrazino-alkyl (aryl) phosphonic acids and their derivatives were prepared from the corresponding hydrazono compounds by treatment with sodium cyanoborohydride or with the borane-tetrahydrofuran complex, respectively. - Key words: Hydrazino-, hydrazono-alkylphosphonates; sodium cyanoborohydride; borane-tetrahydrofuran complex