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389130-06-7

389130-06-7 Structure

389130-06-7 Structure
IdentificationBack Directory
[Name]

(S)-(+)-(8,9,10,11,12,13,14,15-OCTAHYDRO-3,5-DIOXA-4-PHOSPHA-CYCLOHEPTA[2,1-A:3,4-A']DINAPHTHALEN-4-YL)DIMETHYLAMINE
[CAS]

389130-06-7
[Synonyms]

MonoPhos Ligand
3,4-a']dinaphthalen-4-
3,4-a']dinaphthalen-4-yl)dimethylamine,97%
3,4-a']dinaphthalen-4-yl)dimethylamine,99%
(S)-(+)-(8,9,10,11,12,13,14,15-Octahydro-3,5-dioxa-4-phospha-cyclohepta[2,1-a
(S)-(+)-N,N-Dimethyl(8,9,10,11,12,13,14,15-Octahydro-3,5-Dioxa-4-Phospha-Cyclohe
(S)-N,N-Dimethyl-8,9,10,11,12,13,14,15-octahydrodinaphtho-[2,1-d:1',2'-f][1,3,2]dioxaphosphepi
(S)-N,N-Dimethyl-8,9,10,11,12,13,14,15-octahydrodinaphtho-[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4
(11bS)-N,N-dimethyl-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1μ,2μ-f][1,3,2]dioxaphosphepin-4-amine
(11bS)-8,9,10,11,12,13,14,15-octahydro-N,N-diMethyl-Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-aMine
(S)-(+)-(8,9,10,11,12,13,14,15-Octahydro-3,5-dioxa-4-phosphacyclohepta[2.1-a.3.4-a']dinaphthalen-4-yl)dimethylamine
(11bS)-8,9,10,11,12,13,14,15-Octahydro-N,N-dimethyl-di naphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-amine,99%e.e.
(S)-(+)-(8,9,10,11,12,13,14,15-OCTAHYDRO-3,5-DIOXA-4-PHOSPHA-CYCLOHEPTA[2,1-A:3,4-A']DINAPHTHALEN-4-YL)DIMETHYLAMINE
[Molecular Formula]

C22H26NO2P
[MDL Number]

MFCD04117692
[MOL File]

389130-06-7.mol
[Molecular Weight]

367.42
Chemical PropertiesBack Directory
[Melting point ]

112-113°C
[alpha ]

+318° (c 0.63, THF)
[Boiling point ]

523.3±60.0 °C(Predicted)
[storage temp. ]

under inert gas (nitrogen or Argon) at 2-8°C
[form ]

Powder
[pka]

2.15±0.20(Predicted)
[color ]

white
[Optical Rotation]

[α]22/D 282.0°, c = 1 in chloroform
[Sensitive ]

moisture sensitive, store cold
[InChI]

1S/C22H26NO2P/c1-23(2)26-24-19-13-11-15-7-3-5-9-17(15)21(19)22-18-10-6-4-8-16(18)12-14-20(22)25-26/h11-14H,3-10H2,1-2H3
[InChIKey]

OIZQADYWBXZQKE-UHFFFAOYSA-N
[SMILES]

CN(C)P1Oc2ccc3CCCCc3c2-c4c(O1)ccc5CCCCc45
[CAS DataBase Reference]

389130-06-7
Safety DataBack Directory
[Risk Statements ]

36/37/38
[Safety Statements ]

26-36/37/39
[WGK Germany ]

3
[Storage Class]

11 - Combustible Solids
Questions And AnswerBack Directory
[Reaction]

A ligand for enantioselective hydrogenation of prochiral functional olefins. Reactions of 389130-06-7
Hazard InformationBack Directory
[Uses]

(11bS)-N,N-dimethyl-8,9,10,11,12,13,14,15-octahydrodinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-amine is a monodentate phosphoramidite (MonoPhos) chiral ligand that can be used:
  • In the Cu-catalyzed synthesis of chiral 3-(arylbut-1-yn-1-yl)silane derivatives by reacting N-tosylhydrazones with silyl-substituted alkynes via asymmetric insertion.
  • In the Rh-catalyzed asymmetric hydrogenation of R-isopropylcinnamic acid derivative, a key intermediate of renin inhibitor aliskiren.
  • In the Rh-catalyzed conjugate addition of arylboronic acids to lactones, enones, and nitroalkenes.

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