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ChemicalBook--->CAS DataBase List--->500997-69-3

500997-69-3

500997-69-3 Structure

500997-69-3 Structure
IdentificationBack Directory
[Name]

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

500997-69-3
[Synonyms]

(S)-SIPHOS-PE
(R)-SIPHOS-PE
(R)-SIPHOS-PE 97%
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
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)-1PHENYLETHYL]AMINE
(11AS)-(-)-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-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
(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.
(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
[Molecular Formula]

C33H32NO2P
[MDL Number]

MFCD08459342
[MOL File]

500997-69-3.mol
[Molecular Weight]

505.59
Chemical PropertiesBack Directory
[Melting point ]

98-100°C
[alpha ]

+300° (c 1.0, CH2Cl2)
[Boiling point ]

617.8±65.0 °C(Predicted)
[storage temp. ]

?20°C
[form ]

solid
[pka]

0.40±0.20(Predicted)
[color ]

white
[optical activity]

[α]22/D +337°, c = 1 in chloroform
[Sensitive ]

moisture sensitive
[InChIKey]

ZXLQLIDJAURBDD-HRPAVAKOSA-N
Safety DataBack Directory
[Symbol(GHS) ]


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
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethanol-->Sodium hydroxide-->Hydrochloric acid-->Ethyl acetate-->Tetrahydrofuran-->Dichloromethane-->PETROLEUM ETHER-->Toluene-->Triethylamine-->Sodium chloride-->Acetone-->n-Butyllithium-->Sodium bicarbonate-->Hydrogen peroxide-->Palladium-->Hydrogen-->Phosphorus trichloride-->Nickel-->Benzyl chloride-->N,N-Diisopropylethylamine-->Sodium bromide-->Methanesulfonic acid-->Boron tribromide-->3-Hydroxybenzaldehyde-->(R)-1,1'-SPIROBIINDANE-7,7'-DIOL-->Cinchonidine-->CALCIUM HYDRIDE-->(R,R)-(+)-BIS(ALPHA-METHYLBENZYL)AMINE HYDROCHLORIDE-->(R,R)-(+)-BIS(ALPHA-METHYLBENZYL)AMINE HYDROCHLORIDE
Questions And AnswerBack Directory
[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
Hazard InformationBack Directory
[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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