1-(11bS)-Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-ylpyrrolidine

Name: 1-(11bS)-Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-ylpyrrolidine
Brand: ChemScene
Availability: InStock
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CAS No. 627528-96-5
Cat. No. CS-0086852
Purity≥97%
MDL No.None

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Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
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1-(11bS)-Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-ylpyrrolidine|CS-0086852

Structure of 627528-96-5

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Description

This chiral dioxaphosphepine-pyrrolidine moiety integrates a rigid, electron-deficient phosphorus heterocycle with a pyrrolidine nitrogen, enabling precise stereocontrol in asymmetric synthesis. The 11bS configuration ensures predictable diastereoselectivity in transition-metal-catalyzed transformations, while the fused naphthalene units enhance stability and π-stacking potential.

Application

1-(11bS)-Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-ylpyrrolidine serves as a stereochemically defined phosphine ligand that facilitates transition-metal-catalyzed cross-coupling reactions. Its rigid, polycyclic backbone enhances thermal stability and electron-donating capacity, enabling efficient palladium-catalyzed C–C and C–heteroatom bond formations under mild conditions. The structure exhibits robust functional group tolerance and simplifies purification due to low volatility and high bench stability, making it suitable for scalable synthesis and process development in medicinal chemistry workflows.

General Information

CAS No. 627528-96-5
Cat. No. CS-0086852
Purity ≥97%
MDL No. None
Storage 4°C, protect from light, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₄H₂₀NO₂P
Molecular Weight 385.39
Synonym(s) 1-(11bS)-dinaphtho[2,1-d
SMILES C12=CC=CC=C1C=CC3=[C@]2[C@]4=C(C=CC=C5)C5=CC=C4OP(N6CCCC6)O3

Computational Chemistry Data

TPSA 29.52
LogP 7.3282
H_Acceptors 3
H_Donors 0
Rotatable_Bonds 1

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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1-(11bS)-Dinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepin-4-ylpyrrolidine

CAS No. 627528-96-5

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