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456713 Sigma-Aldrich

(DHQD)2AQN

95%

Synonym: Hydroquinidine (anthraquinone-1,4-diyl) diether

  • CAS Number 176298-44-5

  • Empirical Formula (Hill Notation) C54H56N4O6

  • Molecular Weight 857.05

  •  MDL number MFCD00467216

  •  PubChem Substance ID 329756886

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Cinchona Alkaloids, Dihydroxylation,
Quality Level   100
assay   95%
optical activity   [α]/D -498°
mp   165 °C (lit.)
SMILES string   CC[C@@H]1CN2CCC1CC2[C@@H](Oc3ccc(O[C@H](C4CC5CCN4C[C@H]5CC)c6ccnc7ccc(OC)cc67)c8C(=O)c9ccccc9C(=O)c38)c%10ccnc%11ccc(OC)cc%10%11
InChI   1S/C54H56N4O6/c1-5-31-29-57-23-19-33(31)25-45(57)53(39-17-21-55-43-13-11-35(61-3)27-41(39)43)63-47-15-16-48(50-49(47)51(59)37-9-7-8-10-38(37)52(50)60)64-54(46-26-34-20-24-58(46)30-32(34)6-2)40-18-22-56-44-14-12-36(62-4)28-42(40)44/h7-18,21-22,27-28,31-34,45-46,53-54H,5-6,19-20,23-26,29-30H2,1-4H3/t31-,32-,33+,34+,45-,46-,53+,54+/m1/s1
InChI key   ARCFYUDCVYJQRN-ZPCQJLRDSA-N

Description

General description

(DHQD)2AQN is a biscinchona alkaloid.

Application

(DHQD)2AQN may be used to:
• Catalyze the asymmetric cyanation of ketones to form tertiary cyanohydrin carbonates.
• Facilitate the asymmetric ring opening of terminal N-nosylaziridines with trimethylsilyl cyanide.

Superior ligand for asymmetric dihydroxylation reactions of most olefins bearing aliphatic substituents or olefins having heteroatoms in the allylic position.

Packaging

500 mg in amber glass bottle

Legal Information

Sold under license from Rhodia Pharma Solutions.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles

Articles

Barry Sharpless Group – Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Barry Sharpless Group – Professor Product Portal
Keywords: Asymmetric synthesis, Building blocks, Chemical reactions, Click chemistry, Oxidations, Solvents, transformation

Cinchona Alkaloids - Aldrich ChemFiles 2008, 8.2, 74.

Cinchona alkaloids and their derivatives have proven to catalyze an astonishing array of enantioselective transformations, providing access to chiral products of high enantiopurity.1 The presence of ...
William Sommer and Daniel Weibel
Aldrich ChemFiles 2008, 8.2, 74.
Keywords: Addition reactions, Aminations, Antimicrobials, Asymmetric synthesis, Catalysis, Desymmetrizations, Dihydroxylations, Ligands, Reductive aminations

Cinchona Alkaloids - Chemfiles Volume 6 Article 4

Abundant in nature, cinchona alkaloids are readily accessible chiral amine catalysts that exist in pseudoenantiomeric forms. Indeed, some of the very first examples of organocatalyzed reactions were ...
Chemfiles Volume 6 Article 4
Keywords: Addition reactions, Alkylations, Asymmetric synthesis, Building blocks, Catalysis, Desymmetrizations, Dihydroxylations, Halogenations, Ligands, transformation

Cinchona Alkaloids

Asymmetric phase-transfer catalysis (PTC) has been recognized as a “green” alternative to many homogeneous synthetic organic transformations, and has found widespread application. Synthetically modif...
Aldrich ChemFiles 2007, 7.9, 16.
Keywords: Addition reactions, Alkylations, Aminations, Asymmetric synthesis, Catalysis, Methods

Peer-Reviewed Papers
15

References

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