(Dhqd)2phal

Base Information

• Chemical Name: (Dhqd)2phal
• CAS No.: 140853-10-7
• Molecular Formula: C48H54N6O4
• Molecular Weight: 778.98
• Hs Code.: 29392000
• UNII: W4JCP4V5TH
• DSSTox Substance ID: DTXSID30458959
• Nikkaji Number: J1.930.114A
• Mol file: 140853-10-7.mol

Synonyms:(DHQD)2PHAL;140853-10-7;1,4-bis[(S)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methoxy]phthalazine;(Dhqd)2phal [MI];AD-mix-beta;W4JCP4V5TH;Hydroquinidine 1,4-phthalazinediyl diether;Hydroquinidine 1,4-phthalazinediyl ether;1,4-Bis(dihydroquinidine)phthalazine;AD-mix-|A;(DHQD)2 PHAL;AD-mix-ss;Cinchonan, 9,9''-(1,4-phthalazinediylbis(oxy))bis(10,11-dihydro-6'-methoxy-, (9S)-(9''S)-;MFCD00198107;hydroquinidine 1;AD-mix beta;Cinchonan, 9,9''-[1,4-phthalazinediylbis(oxy)]bis[10,11-dihydro-6'-methoxy-, (9S)-(9''S)-;UNII-W4JCP4V5TH;(DHQD)2PHAI;(DHQD)2-PHAL;SCHEMBL541620;DTXSID30458959;YUCBLVFHJWOYDN-HVLQGHBFSA-N;(DHQD)2PHAL, >=95%;1,4-Bis((S)-((1S,2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine;AKOS015950620;GS-3098;1,4-bis[(S)-[(2R,4S,5R)-5-ethylquinuclidin-2-yl]-(6-methoxy-4-quinolyl)methoxy]phthalazine;Hydroquinine-1,4-phthalazinediyl diether;AC-30198;BP-12218;BP-12300;CS-0131722;F10632;A847451;J-007423;Hydroquinidine 1,4-phthalazinediyl diether((DHQD)2PHAL?;Hydroquinidine 1,4-phthalazinediyl diether, (DHQD)2PHAL;1,4-bis((S)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine;1,4-Bis[(S)-(6-methoxy-4-quinolinyl)[(2R,4S,5R)-5-ethylquinuclidine-2-yl]methoxy]phthalazine;1,4-bis[(S)-[(2R,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl](6-methoxyquinolin-4-yl)methoxy]phthalazine

Chemical Property of (Dhqd)2phal

Chemical Property:

• Melting Point: 160 °C (dec.)(lit.)
• Refractive Index: 1.688
• PKA: 9.61±0.70(Predicted)
• PSA: 94.96000
• Density: 1.3 g/cm³
• LogP: 9.10020
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Sparingly)
• XLogP3: 8.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 12
• Exact Mass: 778.42065423
• Heavy Atom Count: 58
• Complexity: 1250

Purity/Quality:

99% ^*data from raw suppliers

(DHQD)2PHAL ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)OC)OC5=NN=C(C6=CC=CC=C65)OC(C7CC8CCN7CC8CC)C9=C1C=C(C=CC1=NC=C9)OC
• Isomeric SMILES: CC[C@H]1CN2CC[C@H]1C[C@@H]2[C@H](C3=C4C=C(C=CC4=NC=C3)OC)OC5=NN=C(C6=CC=CC=C65)O[C@H]([C@H]7C[C@@H]8CCN7C[C@@H]8CC)C9=C1C=C(C=CC1=NC=C9)OC
• Uses: (DHQD)2PHAL is a monomeric cinchona alkaloid dimer used as a catalyst for asymmetric halogenations. (DHQD)2PHAL may be used as ligand for:Osmium trioxide catalyzed asymmetric dihydroxylation of olefins.Palladium catalyzed Suzuki-Miyaura coupling of aryl/heteroaryl halides with aryl boronic acids in aqueous medium and in the absence of phosphine/organic solvent.Copper(I)-catalyzed azide-alkyne cycloaddition reaction to synthesize 1,2,3-triazoles in water.

Technology Process of (Dhqd)2phal

There total 1 articles about (Dhqd)2phal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

1,4-dichlorophthalazine (4752-10-7) + dihydroquinidine (1435-55-8) → (9S,9S)-9,9-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] (140853-10-7)

Guidance literature:

With potassium hydroxide; potassium carbonate; In toluene; for 12h; Heating;

DOI:10.1021/jo00036a003

Reference yield: 75.0%

benzyl bromide (100-39-0) + (9S,9S)-9,9-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] (140853-10-7) → C48H54N6O4C14H14(2+)*2Br(1-)

Guidance literature:

In toluene; for 6h; Heating;

DOI:10.1016/j.tet.2007.05.076

Reference yield:

(9S,9S)-9,9-[phthalazine-1,4-diylbis-(oxy)]bis[10,11-dihydro-6'-methoxycinchonane] (140853-10-7) → 1-(hydrochinidinyl)-4-(benzyloxy)phthalazine

Guidance literature:

Multi-step reaction with 2 steps

1: n-butyllithium / hexane; tetrahydrofuran / 4 h / -78 - 20 °C

2: potassium carbonate; potassium hydroxide / toluene / 6 h / Dean-Stark; Reflux

With n-butyllithium; potassium carbonate; potassium hydroxide; In tetrahydrofuran; hexane; toluene;

DOI:10.1002/chem.201604003

upstream raw materials:

1,4-dichlorophthalazine

dihydroquinidine

Refernces