178098
Glutarimide
98%
Synonym(s):
2,6-Piperidinedione, NSC 58190
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About This Item
Empirical Formula (Hill Notation):
C5H7NO2
CAS Number:
Molecular Weight:
113.11
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
214-340-4
MDL number:
Assay:
98%
Form:
solid
Product Name
Glutarimide, 98%
InChI key
KNCYXPMJDCCGSJ-UHFFFAOYSA-N
InChI
1S/C5H7NO2/c7-4-2-1-3-5(8)6-4/h1-3H2,(H,6,7,8)
SMILES string
O=C1CCCC(=O)N1
assay
98%
form
solid
mp
155-157 °C (lit.)
Quality Level
General description
A glutarimide antibiotic, 9-methylstreptimidone, shows antiviral, antitumor and antifungal activities.
Application
Reactant for:
Thionations
Biocatalytic asymmetric synthesis of chiral amines from ketones applied to sitagliptin manufacture
Synthesis of β-adrenoceptor ligands
Enantioselective synthesis of securinega alkaloids
Intramolecular amidocyclopropanation reactions
Synthesis of alpha-fluoro-alpha amino amides
Thionations
Biocatalytic asymmetric synthesis of chiral amines from ketones applied to sitagliptin manufacture
Synthesis of β-adrenoceptor ligands
Enantioselective synthesis of securinega alkaloids
Intramolecular amidocyclopropanation reactions
Synthesis of alpha-fluoro-alpha amino amides
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Matthew Hoffmann et al.
Cancer chemotherapy and pharmacology, 71(2), 489-501 (2012-12-04)
To investigate the pharmacokinetics and disposition of [(14)C]pomalidomide following a single oral dose to healthy male subjects. Eight subjects were administered a single 2 mg oral suspension of [(14)C]pomalidomide. Blood (plasma), urine and feces were collected. Mass balance of radioactivity
Hung-Wei Chen et al.
Organic letters, 8(14), 3033-3035 (2006-06-30)
[reaction: see text] The reaction of alpha-sulfonyl acetamide 1 with various cyclic unsaturated esters 2 to fused bicyclic glutarimides is reported. Syntheses of (+/-)-alloyohimbane (4) and louisianin D (5) have been accomplished.
Cai-Yun Geng et al.
Journal of computational chemistry, 29(5), 686-693 (2007-09-13)
The reaction mechanism of the Rh-catalyzed [4 + 2] annulation of 4-alkynals with isocyanates is unraveled using density functional calculations. The reaction mechanisms of the model system and the real substituted system have been investigated and the results are compared.
Yohsuke Watanabe et al.
Organic letters, 12(2), 268-271 (2009-12-22)
The boron aldol reaction of beta-substituted glutaric imides bearing an oxazolidinone-based auxiliary proceeds with excellent diastereoselectivity; switching the tertiary amine employed between i-Pr(2)EtN or Et(3)N affords enantiomeric lactone product.
Jianhua Ju et al.
Organic letters, 9(25), 5183-5186 (2007-11-14)
Lactimidomycin (LTM, 1) is a macrolide antitumor antibiotic with a glutarimide side chain from Streptomyces amphibiosporus ATCC53964. To further develop LTM and related analogues as drug candidates we have (i) improved LTM production by approximately 20 fold, (ii) identified three
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