130948-64-0

Upstream product

• 111-24-0 1,5-dibromo-pentane 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 

Downstream Products

• 135603-64-4 α-Aminomethylcyclohexylphosphonic acid 
• 135603-69-9 (1-Ethylaminomethyl-cyclohexyl)-phosphonic acid 
• 135603-70-2 (1-Allylaminomethyl-cyclohexyl)-phosphonic acid 
• 135603-71-3 [(1-Phosphono-cyclohexylmethyl)-amino]-acetic acid 
• 135603-59-7 {[1-(Diethoxy-phosphoryl)-cyclohexylmethyl]-amino}-acetic acid ethyl ester 
• 135603-44-0 {1-[(Diethoxy-phosphorylamino)-methyl]-cyclohexyl}-phosphonic acid diethyl ester 
• 135603-53-1 (1-{[(Diethoxy-phosphoryl)-ethyl-amino]-methyl}-cyclohexyl)-phosphonic acid diethyl ester 
• 135603-54-2 (1-{[Allyl-(diethoxy-phosphoryl)-amino]-methyl}-cyclohexyl)-phosphonic acid diethyl ester 
• 135603-36-0 Diethyl α-aminomethylcyclohexylphosphonate 

Relevant academic research and scientific papers

Substituierte Methylphosphonate als Synthone fuer alicyclische α-funktionalisierte Phosphonate

Syntheses of cycloalkylphosphonates 4, and 6-8 are described, starting from the substituted methylphosphonates 1-3.Hydrolysis of the phosphonic esters 4 and 8 yield the free phosphonic acids 5 and 10; the partial hydrolysis of 7 leads to easily accessible 9.The benzo condensed phosphonates 12 and 13 are formed according to the solvent; a higher boiling medium should be used to obtain 15 and 17. Keywords: Phosphonates; Cycloalkylation and benzo condensed cycloalkylation.

α-FUNCTIONAL CYCLOALKYLPHOSPHONATES. I. SYNTHESIS

Cycloalkylphosphonates 2 of different sizes (from cyclopropyl to cycloheptyl) bearing various functional groups Z in α-position were synthesized by bis-alkylation of α-functional methylphosphonates 1 and ω-dibromoalkanes in presence of base.The choice of the basic system is determined by the nature of Z.With powerful electron-withdrawing groups, NaH-THF/DMSO (Method A, for Z = CN, SO2R) or liquid-solid phase transfer process proved to be the more suitable systems.For Z = aryl or SR, lithium diisopropylamide is required to achieve the deprotonation.A wide range of new phoshonates were obtained in high yields on preparative scale.