Home Other Building Blocks Glycoluril

Glycoluril

CAS No.:
496-46-8
Catalog Number:
AG0039UN
Molecular Formula:
C4H6N4O2
Molecular Weight:
142.1160
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
5g
98%
In Stock USA
United States
$13
- +
25g
98%
In Stock USA
United States
$19
- +
100g
98%
In Stock USA
United States
$50
- +
500g
98%
In Stock USA
United States
$188
- +
Product Description
Catalog Number:
AG0039UN
Chemical Name:
Glycoluril
CAS Number:
496-46-8
Molecular Formula:
C4H6N4O2
Molecular Weight:
142.1160
MDL Number:
MFCD00005539
IUPAC Name:
1,3,3a,4,6,6a-hexahydroimidazo[4,5-d]imidazole-2,5-dione
InChI:
InChI=1S/C4H6N4O2/c9-3-5-1-2(7-3)8-4(10)6-1/h1-2H,(H2,5,7,9)(H2,6,8,10)
InChI Key:
VPVSTMAPERLKKM-UHFFFAOYSA-N
SMILES:
O=C1NC2C(N1)NC(=O)N2
EC Number:
207-821-5
UNII:
U9H2W4OS13
NSC Number:
2765
Properties
Complexity:
165  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
142.049g/mol
Formal Charge:
0
Heavy Atom Count:
10  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
142.118g/mol
Monoisotopic Mass:
142.049g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
82.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.6  
Literature
Title Journal
Hydration of isocyanates in an expandable, self-assembled capsule. Chemical communications (Cambridge, England) 20120904
Encapsulation of ion pairs in extended, self-assembled structures. Journal of the American Chemical Society 20120725
Reversibly expanded encapsulation complexes. Topics in current chemistry 20120101
Self-assembled capsules of unprecedented shapes. Angewandte Chemie (International ed. in English) 20111209
Combinatorial optimization of a molecular glass photoresist system for electron beam lithography. Advanced materials (Deerfield Beach, Fla.) 20111201
Poly[[μ-aqua-triaqua-[μ(6)-1,3,4,6-tetra-kis-(carboxyl-atometh-yl)-7,8-diphenyl-glycoluril]dizinc] monohydrate]. Acta crystallographica. Section E, Structure reports online 20111201
Templated synthesis of glycoluril hexamer and monofunctionalized cucurbit[6]uril derivatives. Journal of the American Chemical Society 20111109
Deconstruction of capsules using chiral spacers. Angewandte Chemie (International ed. in English) 20110919
Bambus[n]urils: a new family of macrocyclic anion receptors. Organic letters 20110805
Recognition properties of acyclic glycoluril oligomers. Organic letters 20110805
(4R,11R)-9-(1-hydroxypropan-2-yl)-4,11-diphenyl-1,3,5,7,9-pentaazatri-cyclo[5.3.1.0]undecane-2,6-dithione. Acta crystallographica. Section E, Structure reports online 20110801
A transparent photo-responsive organogel based on a glycoluril supergelator. Chemical communications (Cambridge, England) 20110714
Encapsulated carboxylic acid dimers with compressed hydrogen bonds. Angewandte Chemie (International ed. in English) 20110110
Molecular clips and tweezers hosting neutral guests. Chemical Society reviews 20110101
Acyclic cucurbit[n]uril congeners are high affinity hosts. The Journal of organic chemistry 20100716
8b,8c-Diphenyl-2,6-bis(4-pyridyl-meth-yl)-perhydro-2,3a,4a,6,7a,8a-hexa-aza-cyclo-penta-[def]fluorene-4,8-dithione chloro-form solvate. Acta crystallographica. Section E, Structure reports online 20100701
3,6,14,17-Tetramethoxy-22,23-diphenyl-1,10,12,21-tetraazahexacyclo[19.2.1.0.0.0.0]tetracosa-2(7),3,5,13(18),14,16-hexaene-11,24-di-thione. Acta crystallographica. Section E, Structure reports online 20100701
Diethyl 7,8,18,19-tetra-methyl-2,13-dioxo-hexa-cyclo-[10.10.2.0.0.0.0]tetra-cosa-5,7,9,16,18,20-hexa-ene-23,24-dicarboxyl-ate. Acta crystallographica. Section E, Structure reports online 20100701
Reasons why aldehydes do not generally participate in cucurbit[n]uril forming reactions. The Journal of organic chemistry 20100507
Adverse health effects due to arsenic exposure: modification by dietary supplementation of jaggery in mice. Toxicology and applied pharmacology 20100201
Microwave synthesis of cucurbit[n]urils. Future medicinal chemistry 20100201
Diethyl 2-tert-butyl-4,11-dioxo-2,3-di-hydro-cis-1H,5H,10H-2,3a,4a,10a,11a-penta-azabenzo[f]indeno[2,1,7-ija]azulene-11b,11c-dicarboxyl-ate. Acta crystallographica. Section E, Structure reports online 20100201
Synthesis of glycoluril catalyzed by potassium hydroxide under ultrasound irradiation. Ultrasonics sonochemistry 20100101
Toxicology and drug delivery by cucurbit[n]uril type molecular containers. PloS one 20100101
Enhanced efficiency of the visible-light photocatalytic hydrogen generation by the ruthenium tris(2,2'-bipyridyl)-methyl viologen system in the presence of cucurbit[n]urils. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20091201
Diethyl 6,13-dioxo-5,7,12,13b,13c,14-hexa-hydro-6H,13H-5a,6a,12a,13a-tetra-azabenz[5,6]azuleno[2,1,8-ija]benz[f]azulene-13b,13c-dicarboxyl-ate 1,2-dichloro-ethane solvate. Acta crystallographica. Section E, Structure reports online 20091101
Glycoluril trimers: selective synthesis and supramolecular properties. Organic letters 20090917
Metal-ion-induced folding and dimerization of a glycoluril decamer in water. Organic letters 20090903
Diethyl 7,8-dibromo-4,11-dioxo-11b,11c-dihydro-5H,10H-2-oxa-3a,4a,10a,11a-tetra-azabenz[f]indeno[2,1,7,7a-ija]azulene-11b,11c-dicarboxyl-ate. Acta crystallographica. Section E, Structure reports online 20090901
Supramolecular rhombic grids formed from bimolecular building blocks. Journal of the American Chemical Society 20090826
N-[2-(6-Methyl-4-oxo-4H-chromen-3-yl)-4-oxothia-zolidin-3-yl]furan-2-carbox-amide N,N-dimethyl-formamide solvate. Acta crystallographica. Section E, Structure reports online 20090801
2,6-Bis(2-chloro-ethyl)-8b,8c-diphenyl-perhydro-2,3a,4a,6,7a,8a-hexa-azacyclo-penta-[def]fluorene-4,8-dithione. Acta crystallographica. Section E, Structure reports online 20090701
2,6-Bis(2-hydroxy-ethyl)-8b,8c-diphenyl-perhydro-2,3a,4a,6,7a,8a-hexa-azacyclo-penta-[def]fluorene-4,8-dithione. Acta crystallographica. Section E, Structure reports online 20090601
Diethyl 1,4-dioxo-1,2,2a,3,4,10b-hexahydro-5H,10H-2,3,4a,10a-tetraaza-benzo[g]cyclopenta[cd]azulene-2a,10b-dicarboxylate. Acta crystallographica. Section E, Structure reports online 20090501
Compressed alkanes in reversible encapsulation complexes. Nature chemistry 20090401
Diethyl 2,6-(2,4-dichloro-phen-yl)-4,8-dioxo-2,3,6,7-tetra-hydro-1H,5H-2,3a,4a,6,7a,8a-hexa-azacyclo-penta-[def]fluorene-8b,8c-dicarboxyl-ate. Acta crystallographica. Section E, Structure reports online 20090401
Diethyl 6,9,17,20-tetra-bromo-2,13-di-oxo-hexa-cyclo-[10.10.2.0.0.0.0]tetra-cosa-5,7,9,16,18,20-hexa-ene-23,24-dicarboxyl-ate. Acta crystallographica. Section E, Structure reports online 20090401
Positron annihilation lifetimes in cucurbiturils: evidence of internal inclusion of gold in CB[7]. Chemphyschem : a European journal of chemical physics and physical chemistry 20090323
Ruthenium(II) complexes of bipyridine-glycoluril and their interactions with DNA. Bioconjugate chemistry 20090318
Cucurbit[n]urils: from mechanism to structure and function. Chemical communications (Cambridge, England) 20090214
4,4'-[8b,8c-Bis(ethoxycarbonyl)-4,8-dioxo-2,3,5,6-tetra-hydro-1H,4H-2,3a,4a,6,7a,8a-hexa-azacyclo-penta-[def]fluorene-2,6-diyl]dipyridinium bis-(tetra-fluorido-borate). Acta crystallographica. Section E, Structure reports online 20080901
1,3,5,7,9,11,13,15-Octa-azapenta-cyclo-[9.5.1.1.0.0]octa-decane-4,8,12,16-tetrone monohydrate: a methyl-ene-bridged glycoluril dimer. Acta crystallographica. Section E, Structure reports online 20080901
Tetrameric molecular bowl assembled from glycoluril building blocks. Chemical communications (Cambridge, England) 20080721
Cucurbit[n]uril formation proceeds by step-growth cyclo-oligomerization. Journal of the American Chemical Society 20080702
Glycoluril dimers bearing hydrogen atoms on their convex face and their self-assembly in the solid state. The Journal of organic chemistry 20080620
Two-dimensional hydrogen-bonded networks in two novel glycoluril derivatives. Acta crystallographica. Section C, Crystal structure communications 20080201
3α,6α-Bis(ethoxy-carbon-yl)glycoluril (diethyl 2,5-dioxoperhydro-imidazo[4,5-d]imidazole-3a,6a-dicarboxyl-ate). Acta crystallographica. Section E, Structure reports online 20080101
13b,13c-Di-2-pyridyl-5,7,12,13b,13c,14-hexa-hydro-6H,13H-5a,6a,12a,13a-tetra-azabenz[5,6]azuleno[2,1,8-ija]benz[f]azulene-6,13-dione methanol hemisolvate. Acta crystallographica. Section E, Structure reports online 20080101
Dipropyl 4,8-dioxo-1H,5H-2,6-dioxa-3a,4a,7a,8a-tetra-azacyclo-penta-[def]fluorene-8b,8c-dicarboxyl-ate. Acta crystallographica. Section E, Structure reports online 20080101
Diethyl 2-tert-butyl-6,9-dibromo-4,11-dioxo-5,10-dihydro-cis-1H,3H,4H,11H-2-azo-3a,4a,10a,11a-tetra-aza-benz[f]indeno[2,1,7-ija]azulene-11b,11c-dicarboxyl-ate. Acta crystallographica. Section E, Structure reports online 20080101
Mechanism of the conversion of inverted CB[6] to CB[6]. The Journal of organic chemistry 20070831
Functionalized cucurbiturils and their applications. Chemical Society reviews 20070201
Longer guests drive the reversible assembly of hyperextended capsules. Angewandte Chemie (International ed. in English) 20070101
Coiled molecules in spring loaded devices. Journal of the American Chemical Society 20061129
Nor-seco-cucurbit[10]uril exhibits homotropic allosterism. Journal of the American Chemical Society 20061122
Avidin and streptavidin ligands based on the glycoluril bicyclic system. Organic & biomolecular chemistry 20060821
Substituent effects control the self-association of molecular clips in the crystalline state. The Journal of organic chemistry 20060609
The inverted cucurbit[n]uril family. Journal of the American Chemical Society 20051228
Cucurbit[n]uril analogues: synthetic and mechanistic studies. The Journal of organic chemistry 20051209
Acyclic congener of cucurbituril: synthesis and recognition properties. The Journal of organic chemistry 20030808
Glycoluril ribbons tethered by complementary hydrogen bonds. Chemical communications (Cambridge, England) 20030721
New supramolecular organization for a glycoluril: chiral hydrogen-bonded ribbons. Chemical communications (Cambridge, England) 20021007
Methylene-bridged glycoluril dimers: synthetic methods. The Journal of organic chemistry 20020809
Diastereoselective formation of glycoluril dimers: isomerization mechanism and implications for cucurbit[n]uril synthesis. Journal of the American Chemical Society 20020717
Enantiomeric self-recognition of a facial amphiphile triggered by [{Pd(ONO2)(en)}2]. Angewandte Chemie (International ed. in English) 20020603
Synthesis of disubstituted cucurbit[6]uril and its rotaxane derivative. Organic letters 20020418
Controlling factors in the synthesis of cucurbituril and its homologues. The Journal of organic chemistry 20011130
'Flexiball' toolkit: a modular approach to self-assembling capsules. Journal of the American Chemical Society 20011128
Self-association of facially amphiphilic methylene bridged glycoluril dimers. Organic letters 20011004
Cucurbituril for water treatment. Part I: Solubility of cucurbituril and sorption of reactive dyes. Water research 20011001
Twisted amides: synthesis and structure of 1,6-dipivaloyl-3,4,7,8- tetramethyl-2,5-dithioglycoluril. Organic letters 20010222
Properties