(DHQD)2AQN - CAS 176298-44-5

(DHQD)2AQN is a cinchona alkaloids organocatalyst that has been intensively applied as either standalone catalysts or chiral ligands in catalytic asymmetric reactions.

Catalog Number

176298-44-5

CAS

176298-44-5

IUPAC Name

1,4-bis[(S)-(5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl)-(6-methoxyquinolin-4-yl)methyl]anthracene-9,10-dione

Synonyms

Hydroquinidine (anthraquinone-1,4-diyl) diether

Application

(DHQD)2AQN is Superior ligand for asymmetric dihydroxylation reactions of most olefins bearing aliphatic substituents or olefins having heteroatoms in th

Molecular Weight

857.05

Molecular Formula

C54H56N4O6

Product Information

Canonical SMILES

O=C1C2=C(C(C3=C(C=CC(OC(C4=CC=NC5=CC=C(C=C45)OC)C6N7CC(C(C6)CC7)CC)=C13)OC(C8=CC=NC9=CC=C(C=C89)OC)C%10N%11CC(C(C%10)CC%11)CC)=O)C=CC=C2

InChI

InChI=1S/C54H52N4O4/c1-5-31-29-57-23-19-33(31)25-47(57)49(37-17-21-55-45-15-11-35(61-3)27-43(37)45)41-13-14-42(52-51(41)53(59)39-9-7-8-10-40(39)54(52)60)50(48-26-34-20-24-58(48)30-32(34)6-2)38-18-22-56-46-16-12-36(62-4)28-44(38)46/h5-18,21-22,27-28,31-34,47-50H,1-2,19-20,23-26,29-30H2,3-4H3/t31?,32?,33?,34?,47?,48?,49-,50-/m0/s1

InChI Key

QUIOWIWSMQWLNP-XJVYWJENSA-N

Purity

95%

MDL

MFCD00467216

Physical State

Solid

Appearance

Powder

Storage

Inert atmosphere. Room Temperature.

Melting Point

165 °C(lit.)

Optical Activity

-498°

WGK Germany

Safety Information

Signal Word

Warning

Precautionary Statement

P261 - P305 - P351 - P338

Hazard Statements

H315 - H319 - H335

Reference Reading

1. Asymmetric recognition and sequential ring opening of 2-substituted-n-nosylaziridines with (dhqd)2aqn and tmsnu.

Yuta Murakami, Mitsuo Komatsu, Satoshi Minakata, Ikumasa Hidaka, Masamitsu Satake, Yuriko Okada. Org Biomol Chem. 2009 Feb 21; 7(4): 641-3. DOI: 10.1039/b821650a. PMID: 19194575.

A new method for asymmetric ring opening of terminal aziridines using a chiral amine, (DHQD)(2)AQN, is described; the reaction is based on the asymmetric recognition of aziridines using (DHQD)(2)AQN and on sequential ring opening using TMSNu.

The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass