Oxazole, 2,2'-(1-methylethylidene)bis[4,5-dihydro-4-phenyl-, (4S,4'S)-

Base Information

• Chemical Name: Oxazole, 2,2'-(1-methylethylidene)bis[4,5-dihydro-4-phenyl-, (4S,4'S)-
• CAS No.: 131457-46-0
• Molecular Formula: C21H22 N2 O2
• Molecular Weight: 334.418
• Hs Code.: 2934999090
• European Community (EC) Number: 678-562-7
• UNII: 6Q4X8PAO1T
• Nikkaji Number: J725.780E
• Wikidata: Q27265321
• Mol file: 131457-46-0.mol

Synonyms:131457-46-0;(4S,4'S)-2,2'-(Propane-2,2-diyl)bis(4-phenyl-4,5-dihydrooxazole);(S,S)-Phbox;Ph-box, (S,S)-;Oxazole, 2,2'-(1-methylethylidene)bis[4,5-dihydro-4-phenyl-, (4S,4'S)-;(S,S)-2,2'-ISOPROPYLIDENE-BIS(4-PHENYL-2-OXAZOLINE);(S,S)-Ph-box [MI];(S,S)-2,2'-Isopropylidenebis(4-phenyl-2-oxazoline);(S,S)-2,2-Bis(4-phenyl-2-oxazolin-2-yl)propane;6Q4X8PAO1T;(4S,4S)-2,2-(Propane-2,2-diyl)bis(4-phenyl-4,5-dihydrooxazole);2,2'-(S)-Isopropylidene-bis(4-phenyl-2-oxazoline);(4S)-4-phenyl-2-[2-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]propan-2-yl]-4,5-dihydro-1,3-oxazole;(-)-2,2'-ISOPROPYLIDENEBIS[(4S)-4-PHENYL-2-OXAZOLINE];(4S,4'S)-2,2'-(1-Methylethylidene)bis(4,5-dihydro-4-phenyloxazole);Oxazole, 2,2'-(1-methylethylidene)bis(4,5-dihydro-4-phenyl-, (4S,4'S)-;C21H22N2O2;(-)-2,2'-Isopropylidenebis[(4S)-4-phenyl-2-oxazoline], 97%;(-)-2,2-BIS[(4S)-4-PHENYL-2-OXAZOLIN-2-YL]PROPANE;(4S)-4-phenyl-2-{2-[(4S)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]propan-2-yl}-4,5-dihydro-1,3-oxazole;Bis(oxazoline) ligands;UNII-6Q4X8PAO1T;(S,S)-ph-box;Bis(oxazoline) ligands (S,S)-ph-box [MI];SCHEMBL917712;JTNVCJCSECAMLD-QZTJIDSGSA-N;AMY25556;BCP26530;MFCD00192245;AKOS015838408;AKOS015913345;CS-W014499;SC11775;AS-72642;I0582;T71709;J-006007;2,2'-isopropylidenebis[(4S)-4-phenyl-2-oxazoline];Q27265321;(S,S)-2,2'-(Dimethylmethylene)bis(4-phenyl-2-oxazoline);(S)-4-phenyl-2-(2-((S)-4-phenyl-4,5-dihydrooxazol-2-yl)propan-2-yl)-4,5-dihydrooxazole;2-[1-methyl-1-(4-phenyl-4,5-dihydro-1,3-oxazol-2-yl)ethyl]-4-phenyl-4,5-dihydro-1,3-oxazole

Chemical Property of Oxazole, 2,2'-(1-methylethylidene)bis[4,5-dihydro-4-phenyl-, (4S,4'S)-

Chemical Property:

• Melting Point: 37-41 °C(lit.)
• Refractive Index: 1.611
• Boiling Point: 193 °C0.03 mm Hg(lit.)
• PKA: 4.85±0.70(Predicted)
• Flash Point: 110 ºC
• PSA: 43.18000
• Density: 1.18g/cm³
• LogP: 3.22380
• Storage Temp.: −20°C
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 334.168127949
• Heavy Atom Count: 25
• Complexity: 482

Purity/Quality:

98%,99%ee ^*data from raw suppliers

(S,S)-2,2''-Isopropylidenebis(4-phenyl-2-oxazoline) ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C1=NC(CO1)C2=CC=CC=C2)C3=NC(CO3)C4=CC=CC=C4
• Isomeric SMILES: CC(C)(C1=N[C@H](CO1)C2=CC=CC=C2)C3=N[C@H](CO3)C4=CC=CC=C4
• Uses: C2 symmetric ligand for enantioselective catalysis. Easily forms bidentate coordination complexes due to the strong affinity of the oxazoline nitrogen for various metals.

Technology Process of Oxazole, 2,2'-(1-methylethylidene)bis[4,5-dihydro-4-phenyl-, (4S,4'S)-

There total 11 articles about Oxazole, 2,2'-(1-methylethylidene)bis[4,5-dihydro-4-phenyl-, (4S,4'S)- 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: 89.0%

2,2-dimethylmalononitrile (7321-55-3) + (2S)-2-phenylglycinol (20989-17-7) → (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline) (131457-46-0,276254-59-2)

Guidance literature:

With zinc(II) chloride; In chlorobenzene; for 24h; Inert atmosphere; Reflux;

DOI:10.1002/chem.201904822

Reference yield: 83.0%

N1-((R)-2-hydroxy-1-phenylethyl)-N3-((S)-2-hydroxy-1-phenylethyl)-2,2-dimethylmalonamide (131457-47-1) → (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline) (131457-46-0,276254-59-2)

Guidance literature:

With ammonium molibdate; In toluene; for 3h; Heating;

DOI:10.1021/ol050543j

Reference yield:

N,N'-Bis-((S)-2-chloro-1-phenyl-ethyl)-2,2-dimethyl-malonamide (131457-48-2) → (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline) (131457-46-0,276254-59-2)

Guidance literature:

With sodium hydroxide; In methanol; water; for 1h; Yield given; Heating;

DOI:10.1021/ja00002a081

upstream raw materials:

N,N'-Bis-((S)-2-chloro-1-phenyl-ethyl)-2,2-dimethyl-malonamide

N¹-((R)-2-hydroxy-1-phenylethyl)-N³-((S)-2-hydroxy-1-phenylethyl)-2,2-dimethylmalonamide

2,2-dimethylmalononitrile

(2S)-2-phenylglycinol