18733-15-8

Usage

Uses

Used in Pharmaceutical Industry:
DIMETHYL[2-(METHOXYCARBONYL)ETHYL]PHOSPHONATE is used as a key intermediate in the synthesis of various drugs, leveraging its reactivity and functional group compatibility for the development of new therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, DIMETHYL[2-(METHOXYCARBONYL)ETHYL]PHOSPHONATE is utilized as a precursor in the production of pesticides and other crop protection chemicals, contributing to its pesticidal properties and effectiveness.
Used in Neurodegenerative Disease Treatment:
DIMETHYL[2-(METHOXYCARBONYL)ETHYL]PHOSPHONATE is studied for its potential application as a treatment for neurodegenerative diseases such as Alzheimer's, due to its ability to inhibit acetylcholinesterase, thereby potentially slowing cognitive decline.
Used as a Reagent in Organic Synthesis:
DIMETHYL[2-(METHOXYCARBONYL)ETHYL]PHOSPHONATE serves as a reagent in organic synthesis, particularly for the formation of phosphonate esters and other functionalized phosphorus compounds, highlighting its versatility in creating a range of chemical entities.
Overall, DIMETHYL[2-(METHOXYCARBONYL)ETHYL]PHOSPHONATE's unique chemical properties and biological activities position it as a valuable compound across multiple industries.

InChI:InChI=1/C6H13O5P/c1-9-6(7)4-5-12(8,10-2)11-3/h4-5H2,1-3H3

Upstream product

• 67-56-1 methanol 
• 96-36-6 methyl phosphite 
• 124-41-4 sodium methylate 
• 292638-85-8 acrylic acid methyl ester 
• 79-10-7 acrylic acid 
• 121-45-9 phosphorous acid trimethyl ester 
• 30337-05-4 2,5-dioxo-2-methoxy-1,2-oxaphospholane 
• 868-85-9 Dimethyl phosphite 
• 20278-51-7 dimethyl methylphosphonite 
• 149-73-5 trimethyl orthoformate 
• 814-68-6 acryloyl chloride 
• 4537-55-7 3--propionsaeure-chlorid 

Downstream Products

• 30337-09-8 3-(dimethoxyphosphinyl)propanoic acid 

Relevant academic research and scientific papers

Synthesizing method for glufosinate-ammonium ammonium salt

The invention relates to a synthesizing method for glufosinate-ammonium ammonium salt. The synthesizing method comprises the following steps: 1) synthesizing methyl methoxyphosphoryl propionate by the reaction of methyl phosphite dimethyl phosphate with methyl acrylate and methyl alcohol; 2) synthesizing 2-[(methyl methoxy)phosphoryl]methyl-3-oxo-butyrate dimethyl ester by the Claisen condensation of methyl methoxyphosphoryl propionate and dimethyl oxalate; 3) under the acidic condition, carrying out the hydrolysis reaction to the 2-[(methyl methoxy)phosphoryl]methyl-3-oxo-butyrate dimethyl ester so as to generate 4-hydroxymethylphosphonic oxide butyric acid; and 4) under the catalyst function, successively reacting with ammonia gas and hydrogen by the 4-hydroxymethylphosphonic oxide butyric acid, and preparing the glufosinate-ammonium ammonium salt. The synthesizing method is capable of avoiding using cyanide poisonous materials. The format reaction is not used, the amount of the solvent used in the production process is small, the reaction condition is moderate and easily controlled, the synthesizing method is suitable for industrial production, the production is safe and convenient to operate, the reaction process is short, and the yield is high.

Me3P-catalyzed addition of hydrogen phosphoryl compounds P(O)H to electron-deficient alkenes: 1 to 1 vs 1 to 2 adducts

Trimethyl phosphine was used as an efficient catalyst for the addition of P(O)-H compounds to electron-deficient alkenes. The addition reactions were generally conducted using a catalytic amount of Me3P under mild reaction conditions. Both 1 to 1 and 1 to 2 adducts were obtained.

PS-BEMP as a basic catalyst for the phospha-Michael addition to electron-poor alkenes

PS-BEMP was used as a heterogeneous catalyst for the phospha-Michael addition of phosphorus nucleophiles to a variety of electron-poor alkenes. The addition reactions were generally performed with equimolar amounts of reagents under solvent free conditions. The protocol proved to be very efficient for the addition to aromatic, non-aromatic and cyclic ketones, giving good yields (78-85%) in all cases. The protocol was also extended with good results to α,β-unsaturated esters and nitriles. This demonstrates that PS-BEMP is a good catalyst for the phospha-Michael addition to electron-poor alkenes.

Synthesis of enantiomerically pure model compounds of the glucose-6-phosphate-T1-translocase inhibitors kodaistatins A-D. Inferences with regard to the stereostructure of the natural products

The kodaistatins A and C (5a,b) inhibit a step in glucose-metabolism at ～100 nM concentrations. This makes them potential 'leads' in the therapy of diabetes. We elucidated the (S)-configuration of the side-chain stereocenter of kodaistatin A by ozonolysis/reduction. The 13C NMR shifts of kodaistatin A model cis-11 suggest that the diol moiety in the dihydroxycyclopentanone core of kodaistatin is trans-configured. This model was prepared from the Feringa lactone (21) and (S)-2-methylbutanal (27) in 23 steps (14 steps in the longest linear sequence). We employed the same strategy for the simplified kodaistatin A model iso-cis-12, which resulted from the same substrates in 11 steps (6 steps in the longest linear sequence). The cyclopentenone cores of both targets stemmed from a C4+C1 approach. The C4 components were masked 'tartaric ketones' (16a,b) and a masked 'tartaric aldehyde' (18), respectively. The C1 components were the lithium-derivatives of the side-chain bearing phosphonates 19 and 22, respectively. The desired acylation/deprotonation/Horner-Wadsworth- Emmons tandem reaction succeeded in a single operation with the 'tartaric aldehyde' 18 but required partly or exclusively additional operations when we incorporated the 'tartaric ketones' 16a or 16b, respectively. The 'tartaric ketones' 16a,b contained an α-siloxyethyl substituent. It is noteworthy that it had to be introduced by adding the benzyltrimethylammonium enolate of lactone 18 to acetaldehyde because the lithium enolate of this lactone fragmented by an acetone-releasing β-elimination.

Thermodynamic study of lanthanide(iii) complexes with bifunctional monophosphinic acid analogues of H4dota and comparative kinetic study of yttrium(iii) complexes

New bifunctional H4dota-like ligands with three acetic acid and one phosphinic acid pendant arms and propionate (H5do3ap PrA) or 4-aminobenzyl (H4do3apABn) reactive groups bound to the phosphorus atom were investigated. Potentiometric studies showed that the ligands have a similar basicity to the parent H4dota and the stability constants of their complexes with sodium(i) and selected lanthanide(iii) ions are also similar. Formation and acid-assisted decomplexation kinetics of yttrium(iii) complexes with a series of H 4dota-like ligands (H4dota and its phosphinic/phosphonic acid analogues) were studied and the reactions are sensitive to a slight modification of the ligand structure. The (2-carboxyethyl)phosphinic acid derivative H5do3apPrA and the phosphonic acid ligand H5do3ap form complexes faster than H4dota. The most kinetically inert complex is that with H4do3apABn. Rates of complexation and decomplexation can depend on the ability to transfer proton(s) outside/inside the complex cavity and, therefore, on the hydrophobicity of the ligands. The results demonstrate that the new bifunctional ligands are suitable for labelling biomolecules with yttrium(iii) radioisotopes for utilization in nuclear medicine. The Royal Society of Chemistry 2007.

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-promoted efficient and versatile aza-Michael addition

A convenient and versatile method was developed for aza-Michael addition using a substoichiometric amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Various nitrogen nucleophiles were efficiently introduced to α,β-unsaturated carbonyl compounds employing 0.5 equiv of DBU. Furthermore, other heteroatomic nucleophiles could also be introduced successfully under the same reaction conditions.

Tetramethylguanidine (TMG)-catalyzed addition of dialkyl phosphites to α,β-unsaturated carbonyl compounds, alkenenitriles, aldehydes, ketones and imines

Tetramethylguanidine-catalyzed addition of dialkyl phosphites to α,β- unsaturated carbonyl compounds, alkenenitriles, aldehydes and ketones constitutes a practical route to a variety of phosphonate synthons. The very mild conditions employed, together with the short reaction times, make the procedure highly versatile and tolerant to a range of functionalities. The proposed methodology is also convenient for the preparation of α- aminophosphonates.

Synthesis of optically-active phosphono analogs of succinates

The present invention relates to catalytic asymmetric hydrogenation of phosphorus analogs of itaconic acid to synthesize novel optically active phosphono succinates.

Process for the preparation of phosphino compounds

Process for the preparation of phosphino compounds Phosphorus-containing compounds of the formula (I) in which R1 and R2 are alkyl, alkoxy or optionally substituted phenyl, R3 and R5 are H, R, optionally substituted phenyl, ROCO--, RO--CO--RO--, halogen, CN, RO--, RO--RO--R-CO--, H2 NCO--, RNHCO-- or RRNCO--, in which R is alkyl, R4 and R6 have the same meaning as defined for R1 and R2 or are a divalent radical in which R7 is oxygen, NR* or sulfur, and R* is H, optionally substituted phenyl or alkyl, are precursors for plant protection agents and fire retardants. According to the invention they can be prepared in high yields and high purity by reacting a compound (R1)(R2)P--OR8, in which R8 is alkyl or optionally substituted phenyl, with an alkene of the formula R3 R4 C=CR5 R6 and at least an equimolar amount of aprotic organic substance such as alcohols, amines, phenols, thiophenols or anilines.