(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE

(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE Basic information
Reaction
Product Name:(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE
Synonyms:(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE;(11AS)-(-)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1-PHENYLETHYL]AMINE;N-DI[(R)-1-PHENYLETHYL]-[(R)-1,1'-SPIROBIINDANE-7,7'-DIYL]-PHOSPHORAMIDITE;N-DI[(R)-1-PHENYLETHYL]-[(S)-1,1'-SPIROBIINDANE-7,7'-DIYL]-PHOSPHORAMIDITE;(11aR)-(+)-10,11,12,13-Tetrahydrodiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine,min.98%(R)-SIPHOS-PE;N-Di[(R)-1-phenylethyl]-[(R)-1,1'-spirobiindane-7,7'-diyl]-phosphoramidite ,98%;(11aR)-(+)-10,11,12,13-Tetrahydrodiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine;(11aR)-10,11,12,13-tetrahydro-N,N-bis[(1R)-1-phenylethyl]-Diindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-aMine
CAS:500997-69-3
MF:C33H32NO2P
MW:505.59
EINECS:
Product Categories:Chiral Phosphine;Chiral Spiro Ligand;CPN
Mol File:500997-69-3.mol
(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE Structure
(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE Chemical Properties
Melting point 98-100°C
alpha +300° (c 1.0, CH2Cl2)
Boiling point 617.8±65.0 °C(Predicted)
storage temp. -20°C
pka0.40±0.20(Predicted)
form solid
color white
optical activity[α]22/D +337°, c = 1 in chloroform
Sensitive moisture sensitive
InChIKeyZXLQLIDJAURBDD-HRPAVAKOSA-N
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36/37
WGK Germany 3
MSDS Information
(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE Usage And Synthesis
Reaction
  1. Chiral ligands for copper-catalyzed asymmetric allylic alkylation with dialkylzincs.
  2. Chiral ligands for copper-catalyzed asymmetric conjugate addition of diethylzinc to enones.
  3. Chiral ligands for palladium-catalyzed asymmetric hydrosilylation of styrenes
  4. Chiral ligands for copper-catalyzed asymmetric ring-opening of oxabicyclic alkenes with Grignard reagents.
  5. Chiral ligands for nickel-catalyzed asymmetric hydrovinylation of α-alkyl vinylarenes.
  6. Chiral ligands for iridium-catalyzed asymmetric hydrogenation of cyclic enamines.
  7. Chiral ligands for iridium-catalyzed asymmetric hydrogenation of cyclic imines.
  8. Chiral ligands for gold-catalyzed asymmetric [2 + 2] cycloaddition reaction.
  9. Chiral ligands for rhodium-catalyzed asymmetric hydroacylation of salicylaldehydes to homoallylic sulfides.
  10. Chiral ligands for palladium-catalyzed asymmetric carboamination reactions. 
Reactions of 500997-69-3_1
Reactions of 500997-69-3_2
Reactions of 500997-69-3_3
Reactions of 500997-69-3_4


Uses(R)-SIPHOS-PE can be used as:
  • A catalyst in the preparation of tricyclic alkaloid (+)-aphanorphine via asymmetric carboamination and Friedel?Crafts reaction.
  • A ligand in the synthesis of chiral ketones via hydroacylation of olefins using salicylaldehyde derivatives.
  • A ligand in the enantioselective synthesis of substituted pyrrolidine derivatives via Pd-catalyzed alkene aminoarylation reactions.

(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE (R,R)-(+)-BIS(ALPHA-METHYLBENZYL)AMINE HYDROCHLORIDE (11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-DIMETHYLAMINE (11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE 3A,4,7,7A-TETRAHYDROINDENE

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