7301-81-7

Upstream product

• 141-52-6 sodium ethanolate 
• 5761-97-7 methyl(phenyl)phosphinic chloride 
• 64-17-5 ethanol 
• 657-37-4 methyl-phenylphosphinicacid-fluoride 
• 91606-80-3 ethyl hyponitrite 
• 34868-25-2 R(+)-Benzyl-methyl-phenyl-phosphin 
• 644-97-3 Dichlorophenylphosphine 
• 7301-81-7 ethyl (S)-methyl(phenyl)phosphinate 
• 6389-79-3 methyl methylphenylphosphinate 
• 2946-61-4 phenylphosphonous acid dimethyl ester 
• 941-69-5 N-phenyl-maleimide 
• 109891-15-8 5-methyl-4-chloro-1-phenyl-1,2-dihydrophosphinine 1-oxide 
• 109891-12-5 3-methyl-4-chloro-1,2-dihydro-1-phenylphosphorin 1-oxide 
• 172487-18-2 ethyl Phenylphosphinate 

Downstream Products

• 7301-82-8 Methyl-phenyl-phosphinsaeure-cyclohexylester 
• 16934-92-2 (R_p)-menthyl methylphenylphosphinate 
• 16934-93-3 (S_p)-Menthylmethylphenylphosphinate 
• 61260-16-0 (4-methoxyphenyl)(methyl)(phenyl)phosphine oxide 
• 81542-32-7 (4-(dimethylamino)phenyl)(methyl)(phenyl)phosphine oxide 
• 90421-02-6 (2,5-dimethoxyphenyl)(methyl)(phenyl)phosphine oxide 
• 42366-51-8 (+/-)-(cyclohexyl(methyl)phenylphosphine) oxide 

Relevant academic research and scientific papers

Stereoselective Transesterification of P-Chirogenic Hydroxybinaphthyl Phosphinates

The substitution reaction of phosphinates with a binaphthyloxy group at the phosphorus atom with lithium alkoxides proceeded with good to high efficiencies to give P-chirogenic phosphinates with a high enantiomeric ratio. As alcohols, primary, secondary, and tertiary alcohols could be used, and the use of tert-butyl alcohol yielded the products with a higher enantiomeric ratio. A substrate with two different alkyl groups on the phosphorus atom could also participate in the substitution reaction to give the corresponding products in good yields with excellent selectivity. The molecular structures of one of the substrates and the corresponding products, determined by X-ray analyses, proved that the substitution reaction at the phosphorus atom proceeded with inversion of the absolute configuration. The usefulness of the reaction was demonstrated by using it to prepare a drug candidate for Duchenne muscular dystrophy. Finally, thionation of the resulting phosphinates was carried out to form P-chirogenic phosphinothioates.

A facile and practical preparation ofP-chiral phosphine oxides

A practical and cost-effective synthetic method ofP-chiral diarylalkyl, aryldialkyl, and triaryl phosphine oxides by using readily available chiral diphenyl-2-pyrrolidinemethanol as the auxiliary is developed. The long-standing racemization issue during s

Dynamic Kinetic Resolution of Phosphinic Acid Derivatives via Nucleophilic Substitution at Phosphorus Center

Reaction of racemic phosphinic acid derivatives with chiral alcohols proceeds with predominant formation of one diastereomer. The highest level of enrichment has been obtained for transesterfication of racemic methyl benzylphenylphosphinate (64% de). The

Alkylation of H-phosphinate esters under basic conditions

(Chemical Equation Presented) An efficient and general procedure was developed for the direct alkylation of H-phosphinate esters with LHMDS at low temperature. The simplicity of the reaction allows the use of various H-phosphinate esters and takes place with a wide range of electrophiles. The approach can be employed to access some GABA analogues or precursors to GABA analogues. The isolated yields are moderate to good. This is the first report of an alkylation with a secondary iodide or a primary chloride.

Novel 2-Phosphabicyclo[2.2.2]oct-5-ene Derivatives and Their Use in Phosphinylations

The [4 + 2] cycloaddition of the double-bond isomers (A and B) of dihydrophosphinine oxide 1 afforded novel phosphabicyclo[2.2.2]oct-5-ene derivates (2-4), formation of which was justified by PM3 semiempirical calculations. The compounds of dimer type (2-

Synthesis and use of 6-, 7-and 8-membered P-heterocycles

The synthesis of new families of P-heterocycles by reductive modifications, ring enlargement and Diels-Alder cycloaddition is described.

Photolysis of the cycloadduct of a 1,2-dihydrophosphinine oxide with N-phenylmaleimide in the presence of protic species: New aspects on the mechanism of the fragmentation of a 2-phosphabicyclo[2.2.2]octene

Phosphabicyclo[2.2.2]octene 2 is useful in the UV light mediated phosphorylation of protic species. Experiments suggest that the fragmentation takes place according to concurrent EA and AE mechanisms.

REACTIONS OF ETHOXY RADICALS WITH OPTICALLY ACTIVE TERTIARY PHOSPHINES. STEREOCHEMISTRY OF THE SUBSTITUTION PROCESS AND THE QUESTION OF PERMUTATION MODES FOR THE POSSIBLE PHOSPHORANYL RADICAL INTERMEDIATES.

The reactions were shown to yield substitution products MePhPOEt and n-PrMePOEt, respectively. Both reactions occur with net inversion of configuration at phosphorus. Optical yields are very sensitive to reaction times and conversions, because the product phosphonites are readily racemized by EtOH formed during reaction. If indeed these substitutions take place via phosphoranyl radicals, then the stereochemistry for reaction of (-)(S)-2 is consistent with the pi * electronic configuration and presumed tetrahedral geometry normally assigned to phenyl-substituted phosphoranyl radicals. Potential trigonal-bipyramidal intermediates are considered with the assumption that the EtO multiplied by (times) in initial adducts is apical and that the PhCH//2 departs exclusively from the apical position.

PHOSPHORORGANISCHE VERBINDUNGEN 99 VERSUCHE ZUR AUFKLAERUNG DER O-SELEKTIVITAET VON VERBINDUNGEN MIT DER P(O)F-GRUPPE

The mechanism of the reaction of phosphoryl fluoride (P(O)F) with alcohols in the presence of an amine is fundamentally different from the reaction of phosphoryl chlorides (P(O)Cl) with primary or secondary amines.The following observations strongly support this proposal: 1. 1H-NMR-, 31P-NMR- and 19F-NMR-spectroscopic investigations show that methyl-phenyl-phosphinicacid-fluoride and n-butylamine form a thermolabile adduct, which yields the methyl-phenyl-phosphinicacid-amide only very slowly. 2.The rate of the reaction of methyl-phenyl-phosphinicacid-fluoride with ethanol is independent of the basicity of the amine but very sensitive to steric factors.Imidazole (which is only a weak base) is surprisingly active. 3.The application of optically active amines as bases in the reaction of racemic methyl-phenyl-phosphinicacid-fluoride with methanol leads to partially optically active methyl-phenyl-phosphinicacid-methylester.This observation proves that the amines are incorporated in the intermediate and have a directing influence on the esterfication process. 4.The reaction mechanism (7) involving a hexacovalent intermediate agrees best with all the known observations.