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280-57-9

280-57-9 | 1,4-Diazabicyclo(2.2.2)octane

CAS No: 280-57-9 Catalog No: AG00384D MDL No:MFCD00006689

Product Description

Catalog Number:
AG00384D
Chemical Name:
1,4-Diazabicyclo(2.2.2)octane
CAS Number:
280-57-9
Molecular Formula:
C6H12N2
Molecular Weight:
112.1729
MDL Number:
MFCD00006689
IUPAC Name:
1,4-diazabicyclo[2.2.2]octane
InChI:
InChI=1S/C6H12N2/c1-2-8-5-3-7(1)4-6-8/h1-6H2
InChI Key:
IMNIMPAHZVJRPE-UHFFFAOYSA-N
SMILES:
C1CN2CCN1CC2
EC Number:
205-999-9
UNII:
X8M57R0JS5
NSC Number:
56362

Properties

Complexity:
61.5  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
112.1g/mol
Formal Charge:
0
Heavy Atom Count:
8  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
112.176g/mol
Monoisotopic Mass:
112.1g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
6.5A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.2  

Literature

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Orthogonal actuation of a supramolecular double-porphyrin tweezer. The Journal of organic chemistry 20100903
Catalytic asymmetric aza-Morita-Baylis-Hillman reaction of methyl acrylate: role of a bifunctional La(O-iPr)3/linked-BINOL complex. Journal of the American Chemical Society 20100901
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Pressure tuning between NH...N hydrogen-bonded ice analogue and NH...Br polar dabcoHBr complexes. The journal of physical chemistry. B 20060525
Solvent exchange in thermally stable resorcinarene nanotubes. Chemistry (Weinheim an der Bergstrasse, Germany) 20060524
Axial coordination changes the morphology of porphyrin assemblies in an organogel system. Organic & biomolecular chemistry 20060521
Rhodium-catalyzed cycloisomerization of N-propargyl enamine derivatives. Journal of the American Chemical Society 20060517
RNA interference as a key to knockdown overexpressed cyclooxygenase-2 gene in tumour cells. British journal of cancer 20060508
DABCO-Induced self-assembly of a trisporphyrin double-decker cage: thermodynamic characterization and guest recognition. Journal of the American Chemical Society 20060426
Synthesis of substituted chromenes through the DABCO-catalyzed reaction of but-3-yn-2-one and methyl propiolate with salicyl N-tosylimines (DABCO = 1,4-diazabicyclo[2.2.2]octane). Chemistry (Weinheim an der Bergstrasse, Germany) 20060412
Perturbation of adsorbed CO by amine derivatives coadsorbed on the gamma-Al2O3 surface: FTIR and first principles studies. The journal of physical chemistry. B 20060316
Design of a magnetic bistability molecular system constructed by H-bonding and pi...pi-stacking interactions. Inorganic chemistry 20060306
1,4-Diazabicyclo[2.2.2]octane derivatives: a novel class of voltage-gated potassium channel blockers. Molecular pharmacology 20060301
Inhibition of apoptosis by p26: implications for small heat shock protein function during Artemia development. Cell stress & chaperones 20060301
Asymmetric transformation of a double-stranded, dicopper(I) helicate containing achiral bis(bidentate) Schiff bases. Inorganic chemistry 20060220
GeO2 natrolite-type infinite four and eight R-containing layers in a 2D pure-Ge framework: Ge3O5(OH)4[C2N2H10]. Inorganic chemistry 20060220
Increased dimensionalities of zinc-diphenic acid coordination polymers by simultaneous or subsequent addition of neutral bridging ligands. Dalton transactions (Cambridge, England : 2003) 20060128
Effects of lipopolysaccharide-induced inflammation on expression of growth-associated genes by corticospinal neurons. BMC neuroscience 20060101
Disruption of nucleocytoplasmic trafficking of cyclin D1 and topoisomerase II by sanguinarine. BMC cell biology 20060101
Comparative maturation of cynomolgus monkey oocytes in vivo and in vitro. Reproductive biology and endocrinology : RB&E 20060101
Serine phosphorylation regulates paxillin turnover during cell migration. Cell communication and signaling : CCS 20060101
Abnormally mild synthesis of bis(dithiolo)pyrroles from 2,5-dimethylpyrroles. Organic letters 20051208
Spectroscopy, NMR and DFT studies on molecular recognition of crown ether bridged chiral heterotrinuclear salen Zn(II) complex. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20051201
Rate-limiting proton-transfer in the sigma-adduct forming reactions of 1,3,5-trinitrobenzene and 4-nitrobenzofuroxan with substituted anilines in dimethyl sulfoxide. Organic & biomolecular chemistry 20051107
Direct synthesis of fused 1,2,3,4,5-pentathiepins. Organic & biomolecular chemistry 20051007
DABCO-catalyzed reaction of alpha-halo carbonyl compounds with dimethyl acetylenedicarboxylate: a novel method for the preparation of polysubstituted furans and highly functionalized 2H-pyrans. The Journal of organic chemistry 20050930
Transition metal carbene chemistry. 4. Nucleophilic attachment of DABCO to fischer carbene complexes in MeCN. Inorganic chemistry 20050808
On the [2,3] sigmatropic rearrangement of allylic nitro compounds. Organic letters 20050804
Photosensitizing properties of 6-methoxy-2-naphthylacetic acid, the major metabolite of the phototoxic non-steroidal anti-inflammatory and analgesic drug nabumetone. Die Pharmazie 20050801
Recyclable and reusable Pd(OAc)2/DABCO/PEG-400 system for Suzuki-Miyaura cross-coupling reaction. The Journal of organic chemistry 20050708
Structural and binding features of cofacial bis-porphyrins with calixarene spacers: pac-man porphyrins that can chew. Chemistry (Weinheim an der Bergstrasse, Germany) 20050704
Self-assembled networks of ribbons in molecular hydrogels of cationic deoxycholic acid analogues. The journal of physical chemistry. B 20050630
Highly efficient solid-phase oxidative cleavage of olefins by OsO4-NalO4 in the intramolecular N-acyliminium Pictet-Spengler reaction. Organic letters 20050623
Efficient palladium-catalyzed homocoupling reaction and Sonogashira cross-coupling reaction of terminal alkynes under aerobic conditions. The Journal of organic chemistry 20050527
A new interpretation of the Baylis-Hillman mechanism. The Journal of organic chemistry 20050513
DABCO catalyzed addition of selenosulfonates to alpha,beta-unsaturated ketones. Organic & biomolecular chemistry 20050507
Efficient Stille cross-coupling reaction catalyzed by the Pd(OAc)2/Dabco catalytic system. The Journal of organic chemistry 20050401
DABCO-directed self-assembly of bisporphyrins (DABCO=1,4-diazabicyclo[2.2.2]octane). Chemistry (Weinheim an der Bergstrasse, Germany) 20050318
Dinuclear zinc(II) dithiocarbamate macrocycles: ditopic receptors for a variety of guest molecules. Dalton transactions (Cambridge, England : 2003) 20050121
Baylis-Hillman mechanism: a new interpretation in aprotic solvents. Organic letters 20050106
Herpesvirus pan encodes a functional homologue of BHRF1, the Epstein-Barr virus v-Bcl-2. BMC microbiology 20050101
Inhibition of Henipavirus fusion and infection by heptad-derived peptides of the Nipah virus fusion glycoprotein. Virology journal 20050101
Hydrogen bonding patterns in the cocrystals of 5-nitrouracil with several donor and acceptor molecules. Beilstein journal of organic chemistry 20050101
Proton-driven self-assembled systems based on cyclam-cored dendrimers and [Ru(bpy)(CN)4]2-. Journal of the American Chemical Society 20041222
Conformation perturbation of p-sulfonatocalix[5]arene via complexation of 1,4-diazabicyclo[2.2.2]octane. Chemical communications (Cambridge, England) 20041221
Photosensitizers neutral red (type I) and rose bengal (type II) cause light-dependent toxicity in Chlamydomonas reinhardtii and induce the Gpxh gene via increased singlet oxygen formation. Environmental science & technology 20041201
The 1:1 adduct of 5-methylbenzene-1,3-diol (orcin) and 1,4-diazabicyclo[2.2.2]octane. Acta crystallographica. Section C, Crystal structure communications 20041001
Photoreactions of p-benzo-, p-naphtho- and p-anthraquinones with ascorbic acid. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20041001
The role of hydrophobic interactions in catalysis of RNA cleavage by 1,4-diazabicyclo[2.2.2]-octane based artificial ribonucleases. Nucleosides, nucleotides & nucleic acids 20041001
Molecular design of artificial ribonucleases using electrostatic interaction. Nucleosides, nucleotides & nucleic acids 20041001
Toward the development of metal-free synthetic nucleases: cleavage of a model substrates by 1,4-diazabicyclo[2.2.2]octane derivatives. Nucleosides, nucleotides & nucleic acids 20041001
Acrylamide in the Baylis-Hillman reaction: expanded reaction scope and the unexpected superiority of DABCO over more basic tertiary amine catalysts. The Journal of organic chemistry 20040917
Dabco as an inexpensive and highly efficient ligand for palladium-catalyzed Suzuki-Miyaura cross-coupling reaction. Organic letters 20040805
Lipid diffusion in sperm plasma membranes exposed to peroxidative injury from oxygen free radicals. Molecular reproduction and development 20040701
A convenient synthesis of new isolable phosphaalkenes using the base-induced rearrangement of secondary vinylphosphines. Inorganic chemistry 20040614
Novel porphyrin-fullerene assemblies: from rotaxanes to catenanes. Organic letters 20040610
Syntheses of functionalized ferratricarbadecaboranyl complexes. Inorganic chemistry 20040531
The role of symmetry and optical selection rules in revealing the molecular structure of the lowest Rydberg and ionic states of the 1,4-diazabicyclo[2.2.2]octane-Arn (n = 1,2,3) van der Waals complexes. The Journal of chemical physics 20040501
[C6N2H14]0.5.[MnAl3(PO4)4(H2O)2]: a manganese(II)-substituted aluminophosphate with AFN topology. Inorganic chemistry 20040419
Reactivities of carboxyalkyl-substituted 1,4,5,8-naphthalene diimides in aqueous solution. Journal of the American Chemical Society 20040407
An investigation of the reaction of 2-aminobenzaldehyde derivatives with conjugated nitro-olefins: an easy and efficient synthesis of 3-nitro-1,2-dihydroquinolines and 3-nitroquinolines. The Journal of organic chemistry 20040305
Straightforward asymmetric entry to highly functionalized 3-substituted 3-hydroxy-beta-lactams via Baylis-Hillman or bromoallylation reactions. The Journal of organic chemistry 20040206
Proton transfer and a dielectric phase transition in the molecular conductor (HDABCO+)2(TCNQ)3. Journal of the American Chemical Society 20040114
Photoprocesses of p-naphthoquinones and vitamin K(1): effects of alcohols and amines on the reactivity in solution. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 20040101
ATF3 upregulation in glia during Wallerian degeneration: differential expression in peripheral nerves and CNS white matter. BMC neuroscience 20040101
[Assessment of the emission of volatile organic compounds from polyurethane foams]. Roczniki Panstwowego Zakladu Higieny 20040101
Photocatalytic actions of the pesticide metabolite 2-hydroxyquinoxaline: destruction of antioxidant vitamins and biogenic amines - implications of organic redox cycling. Redox report : communications in free radical research 20040101
Nicotine-induced Disturbances of Meiotic Maturation in Cultured Mouse Oocytes: Alterations of Spindle Integrity and Chromosome Alignment. Tobacco induced diseases 20040101
Electron transfer and singlet oxygen mechanisms in the photooxygenation of dibutyl sulfide and thioanisole in MeCN sensitized by N-methylquinolinium tetrafluoborate and 9,10-dicyanoanthracene. The probable involvement of a thiadioxirane intermediate in electron transfer photooxygenations. Journal of the American Chemical Society 20031231
Abnormal aza-Baylis-Hillman reaction of N-tosylated imines with ethyl 2,3-butadienoate and penta-3,4-dien-2-one. Organic letters 20031127
Mechanochemical preparation of hydrogen-bonded adducts between the diamine 1,4-diazabicyclo[2.2.2]octane and dicarboxylic acids of variable chain length: an X-ray diffraction and solid-state NMR study. Chemistry (Weinheim an der Bergstrasse, Germany) 20031121
Molecular acrobatics: self-assembly of calixarene-porphyrin cages. Journal of the American Chemical Society 20031119
Photoreduction of p-benzoquinones: effects of alcohols and amines on the intermediates and reactivities in solutions. Photochemistry and photobiology 20031101
Synthesis of novel tetracycles via an intramolecular Heck reaction with anti-hydride elimination. Organic letters 20031002
Assembly of hybrid organic-organometallic materials through mechanochemical acid-base reactions. Chemistry (Weinheim an der Bergstrasse, Germany) 20030922
Do secondary and tertiary ammonium cations act as structure-directing agents in the formation of layered uranyl selenites? Inorganic chemistry 20030908
Synthesis and characterization of materials containing arrays of decavanadate clusters. Frontiers in bioscience : a journal and virtual library 20030901
Surface grafting of glycidyl methacrylate on silica gel and polyethylene beads. Electrophoresis 20030901
Influence of neopterin on the generation of reactive oxygen species in human neutrophils. FEBS letters 20030814
Mycosporine glycine protects biological systems against photodynamic damage by quenching singlet oxygen with a high efficiency. Photochemistry and photobiology 20030801
Organic-organometallic crystal engineering: novel formation of a honeycomb supramolecular architecture of [Re2(mu-OMe)3(CO)6]- anions encapsulating a linear H-bonded chain of [DABCO-H]+ cations. Inorganic chemistry 20030714
Unprecedented conversion of triethylamine and disulfur dichloride into a thienopentathiepin and a heptathiocane. Organic letters 20030529
Ansa versus spiro substitution of cyclophosphazenes: is fluorination essential for ansa to spiro transformation of cyclophosphazenes? Inorganic chemistry 20030519
AgC(CN)3-based coordination polymers. Inorganic chemistry 20030421
Diarylurea-linked zinc porphyrin dimer as a dual-mode artificial receptor: supramolecular control of complexation-facilitated photoinduced electron transfer. Journal of the American Chemical Society 20030409
Does the DABCO-catalysed reaction of 2-hydroxybenzaldehydes with methyl acrylate follow a Baylis-Hillman pathway? Organic & biomolecular chemistry 20030407
Assembly of discrete, one-, two-, and three-dimensional silver(I) supramolecular complexes containing encapsulated acetylide dianion with nitrogen-donor spacers. Inorganic chemistry 20030310
Dual nucleophilic catalysis with DABCO for the N-methylation of indoles. The Journal of organic chemistry 20030307
Correlation between pK(a) and reactivity of quinuclidine-based catalysts in the Baylis-Hillman reaction: discovery of quinuclidine as optimum catalyst leading to substantial enhancement of scope. The Journal of organic chemistry 20030207
Salts of maleic and fumaric acids with organic polyamines: comparison of isomeric acids as building blocks in supramolecular chemistry. Acta crystallographica. Section B, Structural science 20030201
(1R,3S)-Camphoric acid as a building block in supramolecular chemistry: adducts with organic polyamines. Acta crystallographica. Section B, Structural science 20030201
A novel modified baylis-hillman reaction of propiolate. Journal of the American Chemical Society 20030122
Dramatic rate acceleration of the Baylis-Hillman reaction in homogeneous medium in the presence of water. Organic letters 20021226
Mechanochemical assembly of hydrogen bonded organic-organometallic solid compounds. Chemical communications (Cambridge, England) 20021221
Preparation of a bioactive and degradable poly(epsilon -caprolactone)/silica hybrid through a sol-gel method. Biomaterials 20021201
Free-radical hydroxylation reactions of alkylboronates. The Journal of organic chemistry 20021018
The Baylis-Hillman reaction: one-pot facile synthesis of 2,4-functionalized 1,4-pentadienes. The Journal of organic chemistry 20021004
Rapid formation of triarylphosphines by microwave-assisted transition metal-catalyzed C-p cross-coupling reactions. Organic letters 20021003
Ferrocene-1,1'-dicarboxylic acid as a building block in supramolecular chemistry: supramolecular structures in one, two and three dimensions. Acta crystallographica. Section B, Structural science 20021001
Some errors from the crystallographic literature, some amplifications and a questionable result. Acta crystallographica. Section B, Structural science 20021001
The 2:1 complex of maleic acid and 1,4-diazabicyclo[2.2.2]octane: hydrogen-bonded sheets linked by C-H...O hydrogen bonds. Acta crystallographica. Section C, Crystal structure communications 20021001
Encapsulation of diquats by resorcinarenes: a novel staggered anion-solvent mediated hydrogen bonded capsule. Chemical communications (Cambridge, England) 20020907
TiCl(4)-promoted Baylis-Hillman reactions of substituted 5-isoxazolecarboxaldehydes with cycloalkenones). The Journal of organic chemistry 20020809
Synthesis and in vitro studies of novel pyrimidinyl peptidomimetics as potential antimalarial therapeutic agents. Journal of medicinal chemistry 20020801
Chiral versus racemic building blocks in supramolecular chemistry: malate salts of organic diamines. Acta crystallographica. Section B, Structural science 20020601
Isolation and identification of the photodegradation products of the photosensitizing antidepressant drug clomipramine. Phototoxicity studies on erythrocytes. Die Pharmazie 20020601
Chemiluminescence associated with the oxidative metabolism of salicylic acid in rat liver microsomes. Chemico-biological interactions 20020520
Effect of UV-B radiation on some common antibiotics. Toxicology in vitro : an international journal published in association with BIBRA 20020401
Chiral versus racemic building blocks in supramolecular chemistry: tartrate salts of organic diamines. Acta crystallographica. Section B, Structural science 20020401
Involvement of oxidative mechanisms in blue-light-induced damage to A2E-laden RPE. Investigative ophthalmology & visual science 20020401
Dendritic cell density and activation status in human breast cancer -- CD1a, CMRF-44, CMRF-56 and CD-83 expression. British journal of cancer 20020212
Inactivation of maize NADP-malic enzyme by Cu2+-ascorbate. Indian journal of biochemistry & biophysics 20020201
Successful Baylis-Hillman reaction of acrylamide with aromatic aldehydes. The Journal of organic chemistry 20020111
[Chemical ribonucleases. 4. Analysis of the fragment structure of chemical ribonucleases based on 1,4-diazabicyclo[2.2.2]octane]. Bioorganicheskaia khimiia 20020101
Kinetic study of the hydrolysis of phthalic anhydride and aryl hydrogen phthalates. The Journal of organic chemistry 20011116
Layered cobalt hydroxysulfates with both rigid and flexible organic pillars: synthesis, structure, porosity, and cooperative magnetism. Journal of the American Chemical Society 20011031
A self-folding metallocavitand. Journal of the American Chemical Society 20011017
Switch-over in photochemical reaction mechanism from hydrogen abstraction to exciplex-induced quenching: interaction of triplet-excited versus singlet-excited acetone versus cumyloxyl radicals with amines. Journal of the American Chemical Society 20011010
A remarkable rate acceleration of the Baylis-Hillman reaction. Chemical communications (Cambridge, England) 20010907
Efficient Baylis--Hillman reaction using stoichiometric base catalyst and an aqueous medium. The Journal of organic chemistry 20010810
A strategy for the assembly of multiple porphyrin arrays based on the coordination chemistry of Ru-centered porphyrin pentamers. The Journal of organic chemistry 20010629
Light-dependent generation of reactive oxygen species in cell culture media. Free radical biology & medicine 20010615
Salts of 3,5-dinitrobenzoic acid with organic diamines: hydrogen-bonded supramolecular structures in one, two and three dimensions. Acta crystallographica. Section B, Structural science 20010401
Effect of ultraviolet A on ornithine decarboxylase and metallothionein gene expression in mouse skin. Photodermatology, photoimmunology & photomedicine 20010401
Rational design and assembly of M(2)M'(3)L(6) supramolecular clusters with C(3h) symmetry by exploiting incommensurate symmetry numbers. Journal of the American Chemical Society 20010328
Building unit and topological evolution in the hydrothermal DABCO-U-F system. Inorganic chemistry 20010312
Optimization of palladium-catalyzed polyene cyclizations: suppression of competing hydride transfer from tertiary amines with Dabco and an unexpected hydride transfer from 1,4-dioxane. Organic letters 20010125
Photosensitizing activity of thiocolchicoside: photochemical and in vitro phototoxicity studies. Die Pharmazie 20010101

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