335304
(S)-(+)-4-Isopropyl-3-propionyl-2-oxazolidinone
98%
Synonym(s):
(S)-3-Propionyl-4-isopropyl-2-oxazolidinone
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About This Item
Empirical Formula (Hill Notation):
C9H15NO3
CAS Number:
Molecular Weight:
185.22
Beilstein:
3542849
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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Assay
98%
form
liquid
optical activity
[α]25/D +93°, c = 8.7 in methylene chloride
refractive index
n20/D 1.464 (lit.)
bp
102-106 °C/0.75 mmHg (lit.)
density
1.094 g/mL at 25 °C (lit.)
SMILES string
CCC(=O)N1[C@H](COC1=O)C(C)C
InChI
1S/C9H15NO3/c1-4-8(11)10-7(6(2)3)5-13-9(10)12/h6-7H,4-5H2,1-3H3/t7-/m1/s1
InChI key
HOWPHXVPNNPSAZ-SSDOTTSWSA-N
Application
(S)-(+)-4-Isopropyl-3-propionyl-2-oxazolidinone can be used as a building block to prepare:
- (25S)-cholestenoic-26-acid, a potent ligand for the hormonal DAF-12 receptor in Caenorhabditis elegans
- doliculide
Other Notes
Versatile chiral auxiliary for asymmetric synthesis. For a recent review, see Aldrichimica Acta .
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
235.4 °F - closed cup
Flash Point(C)
113 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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Enantioselective total synthesis of doliculide, a potent cytotoxic cyclodepsipeptide of marine origin and structure-cytotoxicity relationships of synthetic doliculide congeners
Hiroyuki I, et al.
Tetrahedron, 50(45), 12853-12882 (1994)
Stereoselective synthesis of the hormonally active (25 S)-δ7-dafachronic acid,(25 S)-δ4-dafachronic acid,(25 S)-dafachronic acid, and (25 S)-cholestenoic acid.
Martin R, et al.
Organic & Biomolecular Chemistry, 6(23), 4293-4295 (2008)
K Iseki et al.
Chemical & pharmaceutical bulletin, 43(11), 1897-1901 (1995-11-01)
A new fluorinated analog of vitamin D2, 24-epi-26,26,26,27,27,27-hexafluoro- 1 alpha,25-dihydroxyvitamin D2, was efficiently synthesized starting from (R)-4-isopropyl-3-propionyl-2- oxazolidinone with high stereochemical control. In all four physiological test systems, the fluorinate vitamin D2 analog was found to be slightly less active
Ager, D.J., et al.
Aldrichimica Acta, 30, 3-3 (1997)
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