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95530-58-8 molecular structure
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(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-one

ChemBase ID: 92245
Molecular Formular: C6H11NO2
Molecular Mass: 129.15704
Monoisotopic Mass: 129.0789786
SMILES and InChIs

SMILES:
N1[C@H](COC1=O)C(C)C
Canonical SMILES:
CC([C@H]1COC(=O)N1)C
InChI:
InChI=1S/C6H11NO2/c1-4(2)5-3-9-6(8)7-5/h4-5H,3H2,1-2H3,(H,7,8)/t5-/m1/s1
InChIKey:
YBUPWRYTXGAWJX-RXMQYKEDSA-N

Cite this record

CBID:92245 http://www.chembase.cn/molecule-92245.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-one
IUPAC Traditional name
(4S)-4-isopropyl-1,3-oxazolidin-2-one
Synonyms
(S)-(-)-4-Isopropyl-2-oxazolidinone
(S)-4-Isopropyl-2-oxazolidinone
4(S)-(1-Methylethyl)-2-oxazolidinone
4(S)-Isopropyloxazolidin-2-one
(S)-(-)-4-Isopropyl-2-oxazolidinone
(4s)-(-)-4-isopropyl-2-oxazolidinone
(4S)-(-)-Isopropyl-2-oxazolidinone
(4R)-4-Isopropyl-1,3-oxazolidin-2-one
(S)-(-)-4-异丙基-2-噁唑烷酮
(4S)-(-)-异丙基-2-恶唑啉酮
CAS Number
95530-58-8
17016-83-0
MDL Number
MFCD00075172
MFCD00010847
Beilstein Number
3588198
PubChem SID
162078943
24881639
24858002
PubChem CID
7157133

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 13.160297  H Acceptors
H Donor LogD (pH = 5.5) 0.94522417 
LogD (pH = 7.4) 0.9452235  Log P 0.94522417 
Molar Refractivity 32.4316 cm3 Polarizability 12.991205 Å3
Polar Surface Area 38.33 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Dichloromethane expand Show data source
Ethanol expand Show data source
Apperance
White to off-White Solid expand Show data source
Melting Point
70-72°C expand Show data source
70-73 °C expand Show data source
70-73 °C(lit.) expand Show data source
70-73°C expand Show data source
70-74°C expand Show data source
Optical Rotation
[α]20/D +14±1°, c = 7% in chloroform expand Show data source
[α]20/D -18°, c = 6 in ethanol expand Show data source
-17 (c=6 in ethanol) expand Show data source
Storage Warning
Irritant expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
TSCA Listed
expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Purity
≥99.0% (sum of enantiomers, GC) expand Show data source
98% expand Show data source
99% expand Show data source
Grade
purum expand Show data source
Optical Purity
ee: 98% (GLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C6H11NO2 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich
Sigma Aldrich - 298883 external link
Application
Reagent employed as a chiral ligand in dirhodium(II) complexes1 and as a chiral auxiliary in aldol addition reactions.2 Versatile chiral auxiliary for asymmetric synthesis. For a recent review, see Aldrichimica Acta.3
Packaging
1, 5 g in glass bottle
Sigma Aldrich - 59660 external link
Other Notes
The 3-acyl derivatives are used in many enantioselective reactions: the 3-propionyl derivative in aldol reactions1,2,3; and alkylations4

REFERENCES

REFERENCES

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  • • Alkyl carboxamides derived from the N-acylation of the oxazolidinone form enolates which undergo highly enantioselective aldol condensation with aldehydes. The products readily undergo hydrolysis, e.g. with base, to give chiral ? -hydroxyacids, with consequent easy recovery and recycle of the chiral auxiliary: J. Am. Chem. Soc., 103, 2127 (1981); Tetrahedron, 27, 897 (1986); Tetrahedron Lett., 31, 4699 (1990); J. Org. Chem., 56, 2489 (1991). For reaction scheme, see (S)-(-)-4-Benzyl-2-oxazolidinone, A18236.
  • • The enolates of the N-acyloxazolidinones can also undergo a variety of other enantioselective reactions including alkylation: J. Am. Chem. Soc., 104, 1737 (1982); acylation: J. Am. Chem. Soc., 106, 1154 (1984):
  • • Bromination (NBS), followed by azide displacement, gives a route to chiral amino acids: Tetrahedron Lett ., 28, 1123 (1987). Direct electrophilic azidation with triisopropylbenzenesulfonyl azide has also been used to effect this transformation: J. Am. Chem. Soc., 112, 4011 (1990).
  • • Chiral auxiliary introduced by Evans for use in enantioselective reactions.
  • • See also (S)-(-)-4-Benzyl-2-oxazolidinone, A18236.
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PATENTS

PATENTS

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INTERNET

INTERNET

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