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77943-39-6

Basic Information
CAS No.: 77943-39-6
Name: (4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE
Article Data: 90
Molecular Structure:
Molecular Structure of 77943-39-6 ((4R,5S)-(+)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE)
Formula: C10H11NO2
Molecular Weight: 177.203
Synonyms: 2-Oxazolidinone,4-methyl-5-phenyl-, (4R-cis)-;(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone;(4R,5S)-4-Methyl-5-phenyl-2-oxazolidinone;(4R,5S)-4-Methyl-5-phenyloxazolidinone;
Density: 1.132 g/cm3
Melting Point: 121-123 °C(lit.)
Boiling Point: 395.8 °C at 760 mmHg
Flash Point: 193.2 °C
Appearance: white to light yellow crystal powder
Hazard Symbols: DangerousN
Risk Codes:  N:;
">  N:;
Safety: 22-24/25
PSA: 38.33000
LogP: 2.18480
Synthetic route
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

779353-80-9

(4R,5S)-3-((E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

A

541511-47-1

(E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoic acid methoxy-methyl-amide

B

77943-39-6

4-methyl-5-phenyloxazolidin-2-one

Conditions
ConditionsYield
Stage #1: N,O-dimethylhydroxylamine*hydrochloride With trimethylaluminum In tetrahydrofuran; toluene at 0 - 20℃;
Stage #2: (4R,5S)-3-((E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one In tetrahydrofuran; toluene at 0℃; for 1h;
A 100%
B 272 mg
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

70-07-5

mephenoxalone

77943-39-6

4-methyl-5-phenyloxazolidin-2-one

Conditions
ConditionsYield
With hydrogenchloride; AlMe3 In tetrahydrofuran; hexane; dichloromethane100%
With hydrogenchloride; AlMe3 In tetrahydrofuran; hexane; dichloromethane100%
With hydrogenchloride; AlMe3 In tetrahydrofuran; hexane; dichloromethane100%
201230-82-2

carbon monoxide

37577-28-9

(1S,2R)-(+)-norphedrine

77943-39-6

4-methyl-5-phenyloxazolidin-2-one

Conditions
ConditionsYield
With copper diacetate; air; palladium diacetate In toluene under 760 Torr; for 2h; Heating;99%
With sodium acetate; palladium diacetate In acetonitrile at 20℃; under 760 Torr; Electrolysis;86%
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

132969-62-1

(2'R,3'S,4'S,4R,5S)-3-[3'-hydroxy-5'-(4"-methoxyphenyl)methoxy-2',4'-dimethylpentanoyl]-5-phenyl-4-methyl-2-oxazolidinone

A

77943-39-6

4-methyl-5-phenyloxazolidin-2-one

B

252342-49-7

(2R,3S,4S)-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentanoic acid methoxymethylamide

Conditions
ConditionsYield
Stage #1: N,O-dimethylhydroxylamine*hydrochloride With trimethylaluminum In tetrahydrofuran; hexane at 0 - 20℃; Metallation;
Stage #2: (2'R,3'S,4'S,4R,5S)-3-[3'-hydroxy-5'-(4"-methoxyphenyl)methoxy-2',4'-dimethylpentanoyl]-5-phenyl-4-methyl-2-oxazolidinone In tetrahydrofuran; hexane at -20℃; for 2.5h; Substitution; Further stages.;
A 80%
B 98%
124-38-9

carbon dioxide

37577-28-9

(1S,2R)-(+)-norphedrine

77943-39-6

4-methyl-5-phenyloxazolidin-2-one

Conditions
ConditionsYield
With triethylamine; acetyl chloride In acetonitrile at -40 - 25℃;97%
Stage #1: carbon dioxide; (1S,2R)-(+)-norphedrine With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 0.75h;
Stage #2: With tributylphosphine; di-tert-butyl-diazodicarboxylate In acetonitrile at 0℃; for 0.333333h; Mitsunobu reaction;
84%
With tetramethylphenylguanidine; chlorophosphoric acid diphenyl ester In acetonitrile at -40 - 20℃;82%
Stage #1: carbon dioxide; (1S,2R)-(+)-norphedrine With N(Et)4(1+)*(2-pyrrolidone-anion) In acetonitrile at 20℃; for 1h; Carboxylation;
Stage #2: With p-toluenesulfonyl chloride In acetonitrile at 20℃; Cyclization; Further stages.;
79%
179927-67-4

(4R,5S)-(+)-(5-benzyloxy-2-fluoro-3-(E)-pentenoyl)-4-methyl-5-phenyl-2-oxazolidinone

A

77943-39-6

4-methyl-5-phenyloxazolidin-2-one

B

179927-65-2

5-O-benzyl-2-deoxy-2-fluoro-L-γ-xylonic lactone

C

179927-64-1

5-O-benzyl-2-deoxy-2-fluoro-D-γ-xylonic lactone

Conditions
ConditionsYield
With osmium(VIII) oxide; trimethylamine-N-oxide In water; acetone; tert-butyl alcohol at 20℃; for 2h; Oxidation; cyclization;A n/a
B 94%
C 86%
102-09-0

bis(phenyl) carbonate

40626-29-7

Acutrim

77943-39-6

4-methyl-5-phenyloxazolidin-2-one

Conditions
ConditionsYield
With potassium carbonate at 110℃; for 6h;93%
Stage #1: bis(phenyl) carbonate; Acutrim With potassium carbonate at 100℃; for 6h;
Stage #2: In methanol for 0.5h; Heating;
954106-23-1

C37H45NO6

A

954106-40-2

C27H36O5

B

77943-39-6

4-methyl-5-phenyloxazolidin-2-one

Conditions
ConditionsYield
With lithium hydroxide; dihydrogen peroxide In tetrahydrofuran at 20℃; for 2h;A 92%
B 79%
128891-59-8

(4R,5S)-3-[(Z)-(R)-2-(tert-Butyl-diphenyl-silanyloxy)-dec-4-enoyl]-4-methyl-5-phenyl-oxazolidin-2-one

A

77943-39-6

4-methyl-5-phenyloxazolidin-2-one

B

126617-76-3

(2R,4Z)-2(tert-Butyldiphenylsiloxy)-4-decen-1-ol

Conditions
ConditionsYield
With lithium borohydride; water In tetrahydrofuran; diethyl ether Product distribution; Ambient temperature; other reducing reagents; var. N-acyloxazolidinones;A n/a
B 90%
109687-75-4

(4R,5S)-3-((R)-2-Benzyl-4-methyl-pent-3-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one

A

77943-39-6

4-methyl-5-phenyloxazolidin-2-one

B

109687-76-5

4-methyl-2(R)-(phenylmethyl)-3-penten-1-ol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at -78 - 0℃; for 1.5h;A 70%
B 90%
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Specification

The (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone with the CAS number 77943-39-6 is also called 2-Oxazolidinone,4-methyl-5-phenyl-, (4R,5S)-. Both the systematic name and IUPAC name are (4R,5S)-4-methyl-5-phenyl-1,3-oxazolidin-2-one. Its molecular formula is C10H11NO2. This chemical belongs to the following product categories: (1)Chiral; (2)Peptide. While using this chemical, you should not breathe dust and avoid it contact with skin and eyes.

The properties of the (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone are: (1)ACD/LogP: 1.88; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.88; (4)ACD/LogD (pH 7.4): 1.88; (5)ACD/BCF (pH 5.5): 15.88; (6)ACD/BCF (pH 7.4): 15.88; (7)ACD/KOC (pH 5.5): 251.93; (8)ACD/KOC (pH 7.4): 251.93; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 29.54 Å2; (13)Index of Refraction: 1.526; (14)Molar Refractivity: 48.07 cm3; (15)Molar Volume: 156.4 cm3; (16)Polarizability: 19.05×10-24cm3; (17)Surface Tension: 36.3 dyne/cm; (18)Enthalpy of Vaporization: 64.6 kJ/mol; (19)Vapour Pressure: 1.79×10-6 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C2O[C@@H](c1ccccc1)[C@H](N2)C
(2)InChI: InChI=1/C10H11NO2/c1-7-9(13-10(12)11-7)8-5-3-2-4-6-8/h2-7,9H,1H3,(H,11,12)/t7-,9-/m1/s1
(3)InChIKey: PPIBJOQGAJBQDF-VXNVDRBHBU