(S)-4-Isopropyl-2-oxazolidinone

Base Information

• Chemical Name: (S)-4-Isopropyl-2-oxazolidinone
• CAS No.: 17016-83-0
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.159
• Hs Code.: 29349990
• European Community (EC) Number: 640-491-4
• DSSTox Substance ID: DTXSID00428109
• Nikkaji Number: J307.690C
• Wikidata: Q72486115
• Mol file: 17016-83-0.mol

Synonyms:17016-83-0;(S)-4-Isopropyl-2-oxazolidinone;(S)-(-)-4-Isopropyl-2-oxazolidinone;(4S)-(-)-4-Isopropyl-2-oxazolidinone;(S)-4-isopropyloxazolidin-2-one;(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-one;(4S)-4-propan-2-yl-1,3-oxazolidin-2-one;2-Oxazolidinone, 4-(1-methylethyl)-, (4S)-;(4S)-4-Isopropyl-1,3-oxazolidin-2-one;(4S)-(-)-Isopropyl-2-oxazolidinone;4(S)-(1-methylethyl)-2-oxazolidinone;MFCD00010847;(4S)-4-Isopropyl-2-oxazolidinone;(S)-(+)-4-Isopropyl-2-oxazolidinone;(4S)-4-isopropyloxazolidin-2-one;(4R)-(+)-4-Isopropyl-2-oxazolidinone;SCHEMBL57409;S-4-Isopropyl-2-oxazolidone;4(S)-isopropyl-2-oxazolidinone;4beta-Isopropyloxazolidine-2-one;DTXSID00428109;4-(S)-isopropyl-2-oxazolidinone;4-(S)-isopropyloxazolidin-2-one;(S)-4-isopropyl-oxazolidin-2-one;4-(S)-isopropyl-oxazolidin-2-one;(4S)-4-isopropyl-oxazolidin-2-one;AKOS006237681;AKOS015838436;4-Isopropyl-1,3-oxazolidin-2-one #;AC-8767;AM81455;CS-W002062;HY-W002062;(4S)-(-)-4-Isopropyl-2-oxazolidone;(S)-( )-4-Isopropyl-2-oxazolidinone;(S)-4-(1-methylethyl)-2-oxazolidinone;4-(S)-(1-Methylethyl)-2-oxazolidinone;AS-12512;(4S)-4-(1-Methylethyl)-2-Oxazolidinone;(4S)-4-iso propyl-1,3-oxazolidin-2-one;A3757;I0451;(S)-(-)-4-Isopropyl-2-oxazolidinone, 99%;EN300-110128;(4S)-2-Oxo-4-(propan-2-yl)-1,3-oxazolidine;J-501465;J-502464

Chemical Property of (S)-4-Isopropyl-2-oxazolidinone

Chemical Property:

• Appearance/Colour: white to off-white solid
• Vapor Pressure: 0.00198mmHg at 25°C
• Melting Point: 70-73 °C(lit.)
• Refractive Index: -17.5 ° (C=6, EtOH)
• Boiling Point: 291.134 °C at 760 mmHg
• PKA: 12.72±0.40(Predicted)
• Flash Point: 129.873 °C
• PSA: 38.33000
• Density: 1.038 g/cm³
• LogP: 1.07960
• Storage Temp.: 0-6°C
• Solubility.: Chloroform, Dichloromethane, Ethanol
• Water Solubility.: Insoluble
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 129.078978594
• Heavy Atom Count: 9
• Complexity: 122

Purity/Quality:

99% ^*data from raw suppliers

(S)-(-)-4-Isopropyl-2-oxazolidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)C1COC(=O)N1
• Isomeric SMILES: CC(C)[C@H]1COC(=O)N1
• Uses: Reagent employed as a chiral ligand in dirhodium(II) complexes and as a chiral auxiliary in aldol addition reactions. Versatile chiral auxiliary for asymmetric synthesis. For a recent review, see Aldrichimica Acta.

Technology Process of (S)-4-Isopropyl-2-oxazolidinone

There total 143 articles about (S)-4-Isopropyl-2-oxazolidinone 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: 99.0%

ethanol (64-17-5) + (S)-N-dodecanoyl-4-isopropyloxazolidinone (153428-19-4) → ethyl laurate (106-33-2) + (4S)-4-isopropyl-1,3-oxazolidin-2-one (17016-83-0)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1055/s-2008-1072587

Reference yield: 99.0%

(S)-N-dodecanoyl-4-isopropyloxazolidinone (153428-19-4) + benzyl alcohol (100-51-6,185532-71-2) → benzyl dodecanoate (140-25-0) + (4S)-4-isopropyl-1,3-oxazolidin-2-one (17016-83-0)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1055/s-2008-1072587

Reference yield: 99.0%

(4S,2'R)-4-iso-propyl-3-(2'-phenylpropionyl)oxazolidin-2-one (311310-18-6) → (R)-2-Phenylpropionic acid (7782-26-5) + (4S)-4-isopropyl-1,3-oxazolidin-2-one (17016-83-0)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 20 ℃; for 12h;

DOI:10.1016/j.tetasy.2007.01.002

upstream raw materials:

phosgene

valinol

4-methoxy-1,3-oxazolidin-2-one

isopropylmagnesium bromide

Downstream raw materials:

(R)-4-isopropyloxazolidin-2-one

(4S)-3-((E)-2-butenoyl)-4-(1-methylethyl)-2-oxazolidinone

(4S)-3-<2'-(4-isobutylphenyl)ethanoyl>-4-(1-methylethyl)2-oxazolidinone

N-isopropyl oxazolidinone

Refernces

• 1、 Minor-Villar, Leticia,Tello-Aburto, Rodolfo,Olivo, Horacio F.,Fuentes, Aydee,Romero-Ortega, Moises. "Desulfurization-oxygenation of chiral 1,3-thiazolidine-2-thiones and 1,3-oxazolidine-2-thiones using propylene oxide and microwave irradiation". . p. 2835 - 2839. Retrieved 2012.
• 2、 Gazvoda, Martin,Hoferl-Prantz, Kathrin,Barth, Roland,Felzmann, Wolfgang,Pevec, Andrej,Ko??mrlj, Janez. "Completely stereocontrolled aldol reaction of chiral ?2-amino acids". . p. 512 - 515. Retrieved 2015.
• 3、 Dong, Xiu-Qin,Liu, Yuanhua,Wang, Heng,Wang, Minyan,Yang, Xuanliang,Yi, Zhiyuan,Yin, Congcong,Zhang, Xumu. "Efficient Access to Chiral 2-Oxazolidinones via Ni-Catalyzed Asymmetric Hydrogenation: Scope Study, Mechanistic Explanation, and Origin of Enantioselectivity". . p. 11153 - 11161. Retrieved 2020/11/23.
• 4、 -. "PROCESS FOR PREPARING OPTICALLY PURE (R)-4-N-PROPYL-DIHYDROFURAN-2(3H)-ONE". . . Retrieved 2019/12/10.