(R)-4-Benzhydryloxazolidin-2-one

Base Information

• Chemical Name: (R)-4-Benzhydryloxazolidin-2-one
• CAS No.: 173604-33-6
• Molecular Formula: C16H15NO2
• Molecular Weight: 253.301
• European Community (EC) Number: 806-304-7
• DSSTox Substance ID: DTXSID00431618
• Nikkaji Number: J1.185.268H
• Mol file: 173604-33-6.mol

Synonyms:173604-33-6;(R)-4-Benzhydryloxazolidin-2-one;(R)-(+)-4-(Diphenylmethyl)-2-oxazolidinone;(4R)-4-benzhydryl-1,3-oxazolidin-2-one;2-Oxazolidinone, 4-(diphenylmethyl)-, (4R)-;(4R)-4-(Diphenylmethyl)-1,3-oxazolidin-2-one;(R)-(+)-4-(DIPHENYLMETHYL)-2-OXAZOLIDIN;(R)-(+)-4-(DIPHENYLMETHYL)-2-OXAZOLIDIN&;SCHEMBL5168082;DTXSID00431618;YGA60433;(4R)-4-Benzhydryloxazolidine-2-one;MFCD01863565;(r)-4-(diphenylmethyl)oxazolidin-2-one;AS-65715;2-Oxazolidinone,4-(diphenylmethyl)-,(4R)-;CS-0132494;E76572;(R)-(+)-4-(Diphenylmethyl)-2-oxazolidinone, 98%

Chemical Property of (R)-4-Benzhydryloxazolidin-2-one

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 145-148 °C(lit.)
• Refractive Index: 1.591
• Boiling Point: 472.603 °C at 760 mmHg
• PKA: 12.29±0.40(Predicted)
• Flash Point: 239.622 °C
• PSA: 38.33000
• Density: 1.181 g/cm³
• LogP: 3.25570
• Storage Temp.: 2-8°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 253.110278721
• Heavy Atom Count: 19
• Complexity: 288

Purity/Quality:

99% ^*data from raw suppliers

(R)-4-Benzhydryloxazolidin-2-one 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(NC(=O)O1)C(C2=CC=CC=C2)C3=CC=CC=C3
• Isomeric SMILES: C1[C@H](NC(=O)O1)C(C2=CC=CC=C2)C3=CC=CC=C3
• Uses: (R)-(+)-4-(Diphenylmethyl)-2-oxazolidinone is used as organic chemical synthesis intermediate.

Technology Process of (R)-4-Benzhydryloxazolidin-2-one

There total 5 articles about (R)-4-Benzhydryloxazolidin-2-one 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: 79.0%

(R)-2-Hydroxymethyl-3,3-diphenyl-propionic acid (204851-65-0) → (4R)-4-(diphenylmethyl)-2-oxazolidinone (173604-33-6,312624-01-4)

Guidance literature:

With diphenyl phosphoryl azide; triethylamine; In toluene; at 80 ℃; for 8h;

DOI:10.1021/jo9720804

Reference yield: 79.0%

(S)-4-(hydroxydiphenylmethyl)oxazolidin-2-one (173604-32-5) → (4R)-4-(diphenylmethyl)-2-oxazolidinone (173604-33-6,312624-01-4)

Guidance literature:

With sodium; In ammonia; for 0.25h;

DOI:10.1016/0040-4039(95)01983-O

Reference yield:

4-(diphenylmethyl)-2-oxazolidinone (312624-01-4) → (4R)-4-(diphenylmethyl)-2-oxazolidinone (173604-33-6,312624-01-4) + (S)-(-)-4-diphenylmethyl-2-oxazolidinone (312624-01-4)

Guidance literature:

With trifluoroacetic acid; In hexane; isopropyl alcohol; Reagent/catalyst; Resolution of racemate;

DOI:10.1002/chir.22766

upstream raw materials:

(S)-4-(hydroxydiphenylmethyl)oxazolidin-2-one

(S)-2-tert-butyl-dimethyl-silanyloxy propanal

4-((R)-4-Benzhydryl-2-oxo-oxazolidin-3-yl)-4-oxo-butyric acid methyl ester

(2R)-2-(tert-butyldimethylsilyloxy)propanal

Downstream raw materials:

(R)-4-Benzhydryl-3-(7-methyl-octanoyl)-oxazolidin-2-one

(R)-4-Benzhydryl-3-hexadecanoyl-oxazolidin-2-one

C₂₃H₂₃NO₃

C₂₄H₂₃NO₅

Refernces

• 1、 Yu, Jeongjae,Armstrong, Daniel W.,Ryoo, Jae Jeong. "Synthesis of new C3 symmetric amino acid- and aminoalcohol-containing chiral stationary phases and application to HPLC enantioseparations". . p. 74 - 84. Retrieved 2017/12/26.
• 2、 Sibi, Mukund P.,Lu, Jianliang,Edwards, Jessica. "A new route to 3-amino sugars. A concise synthesis of L-daunosamine and D-ristosamine derivatives". . p. 5864 - 5872. Retrieved 2007/10/03.