2-(Diphenylphosphino)-N-[(8α,9S)-6'-methoxycinchonan-9-yl]benzamide

Name: 2-(Diphenylphosphino)-N-[(8α,9S)-6'-methoxycinchonan-9-yl]benzamide
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CAS No. 1630973-03-3
Cat. No. CS-0093196
Purity≥97%
MDL No.None

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2-(Diphenylphosphino)-N-[(8α,9S)-6'-methoxycinchonan-9-yl]benzamide|CS-0093196

Structure of 1630973-03-3

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General Information

CAS No. 1630973-03-3
Cat. No. CS-0093196
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 C₃₉H₃₈N₃O₂P
Molecular Weight 611.71
Synonym(s) 2-(diphenylphosphino)-N-[(8α,9S)-6'-methoxycinchonan-9-yl]-Benzamide
SMILES [H][C@]1([C@@H](NC(C2=CC=CC=C2P(C3=CC=CC=C3)C4=CC=CC=C4)=O)C5=C(C=C(OC)C=C6)C6=NC=C5)[N@](C[C@@H]7C=C)CC[C@H]7C1

Description

This phosphine-amide ligand integrates a diphenylphosphino group with a chiral cinchona-derived amide framework, enabling efficient asymmetric catalysis. The rigid scaffold delivers high enantioselectivity in transition-metal-catalyzed reactions, while the methoxy-substituted quinoline enhances solubility and stability under standard conditions.

Application

2-(Diphenylphosphino)-N-[(8α,9S)-6'-methoxycinchonan-9-yl]benzamide serves as a chiral ligand in palladium-catalyzed cross-coupling reactions, enabling efficient asymmetric synthesis of biaryl and alkylated aryl scaffolds. Its rigid cinchona alkaloid framework provides excellent enantiocontrol, while the diphenylphosphino group offers strong metal coordination. The molecule exhibits bench stability, ease of handling, and compatibility with diverse functional groups, making it well-suited for iterative synthesis and scale-up applications in medicinal chemistry and catalytic process development.

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-P330-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 54.46
LogP 6.3691
H_Acceptors 4
H_Donors 1
Rotatable_Bonds 9

Key Words

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2-(Diphenylphosphino)-N-[(8α,9S)-6'-methoxycinchonan-9-yl]benzamide

CAS No. 1630973-03-3

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