(+)-2,2'-Isopropylidenebis[(4R)-4-phenyl-2-oxazoline]

Base Information

• Chemical Name: (+)-2,2'-Isopropylidenebis[(4R)-4-phenyl-2-oxazoline]
• CAS No.: 150529-93-4
• Molecular Formula: C21H22 N2 O2
• Molecular Weight: 334.418
• Hs Code.: 29349990
• European Community (EC) Number: 625-198-1
• UNII: CG7P67W7W0
• Nikkaji Number: J725.781C
• Wikidata: Q27275445
• Mol file: 150529-93-4.mol

Synonyms:150529-93-4;(+)-2,2'-Isopropylidenebis[(4R)-4-phenyl-2-oxazoline];(R,R)-Ph-box;Ph-box, (R,R)-;(R,R)-2,2'-Isopropylidenebis(4-phenyl-2-oxazoline);(R,R)-Ph-box [MI];(R,R)-2,2'-(Dimethylmethylene)bis(4-phenyl-2-oxazoline);(4R,4'R)-2,2'-(propane-2,2-diyl)bis(4-phenyl-4,5-dihydrooxazole);(R,R)-2,2-Isopropylidenebis(4-phenyl-2-oxazoline);CG7P67W7W0;OXAZOLE, 2,2'-(1-METHYLETHYLIDENE)BIS[4,5-DIHYDRO-4-PHENYL-, (4R,4'R)-;(4R)-4-phenyl-2-[2-[(4R)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]propan-2-yl]-4,5-dihydro-1,3-oxazole;2,2-Bis((4R)-4,5-dihydro-4-phenyloxazol-2-yl)propane;Oxazole, 2,2'-(1-methylethylidene)bis(4,5-dihydro-4-phenyl-, (4R,4'R)-;C21H22N2O2;trans-2,2'-(Propane-2,2-diyl)bis(4-phenyl-4,5-dihydrooxazole);(R,R)-2,2/'-(DIMETHYLMETHYLENE)BIS(4-PHENYL-2-OXAZOLINE);302598-31-8;UNII-CG7P67W7W0;(4R)-4-phenyl-2-{2-[(4R)-4-phenyl-4,5-dihydro-1,3-oxazol-2-yl]propan-2-yl}-4,5-dihydro-1,3-oxazole;Bis(oxazoline) ligands (R,R)-ph-box [MI];Bis(oxazoline) ligands derivative (R,R)-ph-box;SCHEMBL249479;JTNVCJCSECAMLD-ROUUACIJSA-N;AMY25577;MFCD00192244;AKOS015838409;CS-W011367;FS-6030;SC11772;D2823;T70318;(R,R)-2,2-Bis(4-phenyl-2-oxazolin-2-yl)propane;J-008716;(R,R)-2,2'-Bis(4-phenyl-2-oxazolin-2-yl)propane;2,2'-isopropylidenebis[(4R)-4-phenyl-2-oxazoline];2,2-bis[(4r)-4-phenyl-1,3-oxazolin-2-yl] propane;Q27275445;(+)-2,2'-Isopropylidenebis[(4R)-4-phenyl-2-oxazoline], 97%;944475-59-6

Chemical Property of (+)-2,2'-Isopropylidenebis[(4R)-4-phenyl-2-oxazoline]

Chemical Property:

• Melting Point: 56-58 °C(lit.)
• Refractive Index: 1.611
• Boiling Point: 468.9°Cat760mmHg
• PKA: 4.85±0.70(Predicted)
• Flash Point: 190.5°C
• 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%, ^*data from raw suppliers

(4R,4''R)-2,2''-(Propane-2,2-diyl)bis(4-phenyl-4,5-dihydrooxazole) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 26-36-45

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: (+)-2,2′-Isopropylidenebis[(4R)-4-phenyl-2-oxazoline] in the presence of copper iodide, can catalyze the asymmetric cyclopropanation reaction of phenyliodonium ylides with alkenes to form cyclopropane α-amino acid esters.

Technology Process of (+)-2,2'-Isopropylidenebis[(4R)-4-phenyl-2-oxazoline]

There total 2 articles about (+)-2,2'-Isopropylidenebis[(4R)-4-phenyl-2-oxazoline] 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: 83.0%

N1,N3-bis((R)-2-hydroxy-1-phenylethyl)-2,2-dimethylmalonamide → (4R,4'R)-2,2'-(propane-2,2'diyl)bis(4-phenyl-4,5-dihydrooxazole) (150529-93-4,276254-59-2)

Guidance literature:

With ammonium molybdate; In toluene; for 3h; Inert atmosphere; Dean-Stark; Reflux;

DOI:10.1039/d1ob00604e

Reference yield:

(S,S)-2,2'-methylenebis(4-phenyl-2-oxazoline) (132098-59-0) + methyl iodide (74-88-4) → (4R,4'R)-2,2'-(propane-2,2'diyl)bis(4-phenyl-4,5-dihydrooxazole) (150529-93-4,276254-59-2)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; for 72h;

DOI:10.1039/c3cy00232b

Reference yield: 85.0%

[Cu(NCMe)4](bis[(R)-1,1'-bi-2-naphtholato]borate) + dichloromethane (75-09-2) + (S,S)-2,2'-isopropylidenebis(4-phenyl-2-oxazoline) (131457-46-0,276254-59-2) + (4R,4'R)-2,2'-(propane-2,2'diyl)bis(4-phenyl-4,5-dihydrooxazole) (150529-93-4,276254-59-2) → (Cu((C6H5C3H3ON)2C(CH3)2)2)(1+)*B((C10H6O)2)2(1-)*0.5CH2Cl2=(((C6H5C3H3ON)2C(CH3)2)2Cu)(B((C10H6O)2)2)*0.5CH2Cl2

Guidance literature:

In acetonitrile; under inert atm. to soln. Cu complex in MeCN (R,R)- and (S,S)-2,2'isopropylidenebis(4-phenyl-2-oxazoline) were added; soln. was concd., Et2O was added, ppt. was dissolved in CH2Cl2 and recrystd. by addn. pentane; elem. anal.;

DOI:10.1139/v03-141

upstream raw materials:

(S,S)-2,2'-methylenebis(4-phenyl-2-oxazoline)

methyl iodide

Refernces

• 1、 Silva, Ana Rosa,Carneiro, Liliana,Carvalho, Ana P.,Pires, Joao. "Asymmetric benzoylation of hydrobenzoin by copper(ii) bis(oxazoline) anchored onto ordered mesoporous silicas and their carbon replicas". . p. 2415 - 2424. Retrieved 2013/09/02.