135613-99-9

Basic information

• Product Name: (R,S)-(3al,7al,1'lu)-1,3-dibenzyloctahydro-2-(4'-methyl-1',2'-pentadienyl)-1H-1,3,2-benzodiazaphosphole 2-oxide
• CAS NO: 135613-99-9
• Molecular Weight: 420.535
• Mol File: 135613-99-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (R,S)-(3al,7al,1'lu)-1,3-dibenzyloctahydro-2-(4'-methyl-1',2'-pentadienyl)-1H-1,3,2-benzodiazaphosphole 2-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: (R,S)-(3al,7al,1'lu)-1,3-dibenzyloctahydro-2-(4'-methyl-1',2'-pentadienyl)-1H-1,3,2-benzodiazaphosphole 2-oxide(135613-99-9)
• EPA Substance Registry System: (R,S)-(3al,7al,1'lu)-1,3-dibenzyloctahydro-2-(4'-methyl-1',2'-pentadienyl)-1H-1,3,2-benzodiazaphosphole 2-oxide(135613-99-9)

Safety Data

• Hazardous Substances Data: 135613-99-9(Hazardous Substances Data)

Upstream product

• 565-68-4 4-methylpent-1-yn-3-ol 
• 65838-10-0 N,N′-dibenzyl-(±)-trans-1,2-diaminocyclohexane 
• 3187-82-4 (±)-trans-N,N′-1,2-cyclohexylenebis(benzylideneamine) 
• 1121-22-8 trans-1,2-Diaminocyclohexane 

Downstream Products

• 135614-36-7 (R,S)-(3al,7al,3'lu)-1,3-dibenzyloctahydro-2-<3'-isopropyl-2'-oxo-5'-hexen-1'-yl>-1H-1,3,2-benzodiazaphosphole 2-oxide 
• 135614-18-5 (R,S)-(2'E)-(3al,7al)-1,3-dibenzyl-2-<4'-methyl-2'-(2''-propenyloxy)-2'-pentenyl>octahydro-1H-1,3,2-benzodiazaphosphole 2-oxide 

Relevant articles and documents

Carbanion-Accelerated Claisen Rearrangements. 8. Phosphonamide Anion-Stabilizing Groups

The utility of various phosphonamide groups has been examined in the context of the carbanion-accelerated Claisen rearrangement (CACR).An extensive survey has identified the N,N'-dibenzyl-1,3,2-diazaphospholidine group 11 to be optimal in the ease of construction of the CACR precursors and the facility and stereoselectivity of the rearrangement.Using n-butyllithium as the base, the phosphonamides rearranged readily at -20 deg C with complete regioselectivity and in good yield (74-79percent).The phosphonates also showed a high level of diastereoselectivity (>95percent de) but the yield from the (Z)-2-butenyl precursor (anti product) was only 45percent.A chiral N,N'-dibenzyl-1,3,2-diazaphospholidine 12 derived from trans-1,2-cyclohexanediamine was examined.Although the CACR proceeded very cleanly (71-85percent) and with high internal selectivity (94percent de), the relative asymmetric induction was poor (16-20percent de).This was also the case for a chiral N,N'-dibenzyl-1,3,2-diazaphosphorinane 15 derived from (R,R)-1,3-diphenyl-1,3-propanediamine and N,N'-dibenzyl-1,3,2-diazaphosphepine 16 derived from 6,6'-dimethyl-2,2'-diaminobiphenyl.The characteristic features of the CACR were compared with the aryl sulfone and phosphonate versions.