2,5-Diphenyl-4,6-bis(dihydroquinine)pyrimidine - ≥97% , CAS No.149820-65-5

CAS: 149820-65-5 Cat. No.: H137471 Molecular Weight: 881.11 EC Number: 604-704-4

GRADE & PURITY ≥97%

Synonyms

AC-30191 | (3R,3'R,4S,4'S,6S,6'S)-6,6'-((1R,1'R)-(2,5-diphenylpyrimidine-4,6-diyl)bis(oxy)bis((6-methoxyquinolin-4-yl)methylene))bis(3-ethylquinuclidine) | Hydroquinine 2,5-diphenyl-4,6-pyrimidinediyl diether | J-008628 | (3R,3'R,4S,4'S,6S,6'S)-6,6'-((1R,

Storage

Room temperature

Shipped In

Normal

Overview

(DHQ)2Pyr is a bis-Cinchona alkaloid ligand used in enantioselective synthesis applications. Cinchona alkaloids catalyze many useful processes with high enantioselectivities. Cinchona alkaloids can be used as bases to deprotonate substrates with relatively acidic protons forming a contact ion pair between the resulting anion and protonated amine. This interaction leads to a chiral environment around the anion and permits enantioselective reactions with electrophiles. Amination with diimides at the remote γ-position can be carried out using (DHQ)2Pyr to form a diverse range of highly functionalized amine compounds.
A bis-Cinchona alkaloid ligand used in enantioselective synthesis applications.

Specifications

Synonyms

AC-30191 | (3R, 3'R, 4S, 4'S, 6S, 6'S)-6, 6'-((1R, 1'R)-(2, 5-diphenylpyrimidine-4, 6-diyl)bis(oxy)bis((6-methoxyquinolin-4-yl)methylene))bis(3-ethylquinuclidine) | Hydroquinine 2, 5-diphenyl-4, 6-pyrimidinediyl diether | J-008628 | (3R, 3'R, 4S, 4'S, 6S, 6'S)-6, 6'-((1R,

Specifications & Purity

≥97%

Storage

Room temperature

Shipped In

Normal

Purity

≥97%

Names and Identifiers

• Pubchem Sid: 504765976
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504765976
• Canonical Smiles: CCC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)OC)OC5=C(C(=NC(=N5)C6=CC=CC=C6)OC(C7CC8CCN7CC8CC)C9=C1C=C(C=CC1=NC=C9)OC)C1=CC=CC=C1
• IUPAC Name: 4-[(R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-[6-[(R)-[(2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methoxy]-2,5-diphenylpyrimidin-4-yl]oxymethyl]-6-methoxyquinoline
• InChIKey: SWKRDCRSJPRVNF-CVCJRGCISA-N
• INCHI: 1S/C56H60N6O4/c1-5-35-33-61-27-23-39(35)29-49(61)52(43-21-25-57-47-19-17-41(63-3)31-45(43)47)65-55-51(37-13-9-7-10-14-37)56(60-54(59-55)38-15-11-8-12-16-38)66-53(50-30-40-24-28-62(50)34-36(40)6-2)44-22-26-58-48-20-18-42(64-4)32-46(44)48/h7-22,25-26,31-32,35-36,39-40,49-50,52-53H,5-6,23-24,27-30,33-34H2,1-4H3/t35-,36-,39-,40-,49-,50-,52+,53+/m0/s1
• Isomeric SMILES: CC[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](C3=C4C=C(C=CC4=NC=C3)OC)OC5=C(C(=NC(=N5)C6=CC=CC=C6)O[C@@H]([C@@H]7C[C@@H]8CCN7C[C@@H]8CC)C9=C1C=C(C=CC1=NC=C9)OC)C1=CC=CC=C1
• WGK Germany: 3
• Molecular Weight: 881.11
• Reaxy-Rn: 39973105
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=39973105&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Cinchona alkaloids

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Cinchona alkaloids
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Cinchona alkaloids
• Alternative Parents: Phenylpyrimidines Quinolines and derivatives Quinuclidines Anisoles Aralkylamines Alkyl aryl ethers Pyridines and derivatives Piperidines Benzene and substituted derivatives Heteroaromatic compounds Trialkylamines Azacyclic compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Cinchonan-skeleton - 5-phenylpyrimidine - Quinoline - Anisole - Phenol ether - Quinuclidine - Alkyl aryl ether - Aralkylamine - Monocyclic benzene moiety - Benzenoid - Pyrimidine - Pyridine - Piperidine - Heteroaromatic compound - Tertiary aliphatic amine - Tertiary amine - Azacycle - Ether - Organoheterocyclic compound - Amine - Organic nitrogen compound - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Organic oxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as cinchona alkaloids. These are alkaloids structurally characterized by the presence of the cinchonan skeleton, which consists of a quinoline linked to an azabicyclo[2.2.2]octane moiety.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in methanol.
• Molecular Weight: 881.100 g/mol
• XLogP3: 11.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 14
• Exact Mass: 880.468 Da
• Monoisotopic Mass: 880.468 Da
• Topological Polar Surface Area: 95.000 Ų
• Heavy Atom Count: 66
• Formal Charge: 0
• Complexity: 1440.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1