(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
• General Description: (DHQD)2PHAL is a chiral ligand derived from hydroquinidine, commonly used in asymmetric catalysis to achieve high enantioselectivity in organic transformations, such as the vinylation of azlactones. It functions as a key catalyst in enantioselective reactions, enabling the synthesis of enantioenriched α-vinyl quaternary amino acids with good yields and high stereocontrol (up to 86% ee). Its utility extends to further functionalization reactions, underscoring its importance in medicinal and synthetic chemistry.

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

One-Pot Vinylation of Azlactones: Fast Access to Enantioenriched α-Vinyl Quaternary Amino Acids

10.1002/ejoc.201700353

The study presents an efficient one-pot protocol for the synthesis of enantioenriched α-vinyl quaternary amino acids, which are important building blocks in medicinal chemistry and biology. The key chemicals used in the study include azlactones (oxazol-5-(4H)-ones), 2-(phenylselanyl)acetaldehyde, and catalytic chiral bases such as the Sharpless ligand (DHQD)2PHAL. Azlactones serve as substrates for the synthesis, 2-(phenylselanyl)acetaldehyde is used in the aldol addition step, and (DHQD)2PHAL is employed to achieve enantioselectivity in the reaction. The process involves aldol addition followed by dehydroxyselenation, resulting in the formation of α-vinyl quaternary amino acids with good overall yields (62–78%) and high enantioselectivity (up to 86% ee). The study also demonstrates the potential for further functionalization of the synthesized amino acids, such as through a Heck coupling reaction.

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