ChemicalBook >> CAS DataBase List >>(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

CAS No.
500997-69-3
Chemical Name:
(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE
Synonyms
(S)-SIPHOS-PE;(R)-SIPHOS-PE;(RA,R,R)-SIPHOS-PE;(R)-SIPHOS-PE 97%;(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE;1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE;N-DI[(R)-1-PHENYLETHYL]-[(S)-1,1'-SPIROBIINDANE-7,7'-DIYL]-PHOSPHORAMIDITE;N-DI[(R)-1-PHENYLETHYL]-[(R)-1,1'-SPIROBIINDANE-7,7'-DIYL]-PHOSPHORAMIDITE;N-Di[(R)-1-phenylethyl]-[(R)-1,1'-spirobiindane-7,7'-diyl]-phosphoramidite ,98%;N,N-bis[(1R)-1-phenylethyl]-4,5,6,7-tetrahydroiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-12-amine
CBNumber:
CB4471613
Molecular Formula:
C33H32NO2P
Molecular Weight:
505.59
MDL Number:
MFCD08459342
MOL File:
500997-69-3.mol
MSDS File:
SDS
Last updated:2023-04-23 13:52:06

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

Melting point 98-100°C
alpha +300° (c 1.0, CH2Cl2)
Boiling point 617.8±65.0 °C(Predicted)
storage temp. -20°C
pka 0.40±0.20(Predicted)
form solid
color white
optical activity [α]22/D +337°, c = 1 in chloroform
Sensitive moisture sensitive
InChIKey ZXLQLIDJAURBDD-HRPAVAKOSA-N

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P305+P351+P338
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36/37
WGK Germany  3

(11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE:1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE price More Price(6)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 700770 (R)-SIPHOS-PE 97% 500997-69-3 50mg $190 2022-05-15 Buy
Strem Chemicals 15-5162 (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 500997-69-3 100mg $160 2024-03-01 Buy
Strem Chemicals 15-5162 (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 500997-69-3 500mg $632 2024-03-01 Buy
ChemScene CS-0037331 (R)-SIPHOS-PE ≥97.0% 500997-69-3 50mg $95 2021-12-16 Buy
ChemScene CS-0037331 (R)-SIPHOS-PE ≥97.0% 500997-69-3 100mg $185 2021-12-16 Buy
Product number Packaging Price Buy
700770 50mg $190 Buy
15-5162 100mg $160 Buy
15-5162 500mg $632 Buy
CS-0037331 50mg $95 Buy
CS-0037331 100mg $185 Buy

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

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.

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(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 (R)-SIPHOS-PE 97% (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,99%e.e. 1',7'-FG][1,3,2]DIOXAPHOSPHOCIN-5-BIS(R)-1PHENYLETHYL]AMINE N,N-bis[(1R)-1-phenylethyl]-4,5,6,7-tetrahydroiindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-12-amine (11AR)-(+)-10,11,12,13-TETRAHYDRODIINDENO[7,1-DE Diindeno[7,1-de:1',7'-fg][1,3,2]dioxaphosphocin-5-amine,10,11,12,13-tetrahydro-N,N-bis[(1R)-1-phenylethyl]-, (11aR)- (11aR)-(+)-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 (R)-SIPHOS-PE,(R,R,R)-SIPHO,N-Di[(R)-1-phenylethyl]-[(R)-1,1′-spirobiindane-7,7′-diyl]-phosphoramidite (S)-SIPHOS-PE (R)-SIPHOS-PE (RA,R,R)-SIPHOS-PE (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 500997-69-3 Chiral Phosphine Chiral Spiro Ligand CPN