14968-74-2

Usage

Structure

Bicyclic organic compound
Quaternary ammonium center

Origin

Derivative of tropane
Naturally occurring alkaloid found in various plants

Usage

Organic synthesis
Building block for the preparation of various pharmaceuticals and organic compounds

Pharmacological properties

Ability to bind and modulate neurotransmitter receptors
Central nervous system activity

Potential applications

Anti-cancer and anti-viral agents

Importance

Versatile and significant chemical compound
Applications in multiple fields

Upstream product

• 280-57-9 1,4-diaza-bicyclo[2.2.2]octane 
• 74-88-4 methyl iodide 

Relevant academic research and scientific papers

A multiaxial molecular ferroelectric with record highTCdesigned by intermolecular interaction modulation

Through precise and ingenious molecular modification, we successfully obtained a multiaxial ferroelectric, [FEtDabco]ZnI3(N-fluoroethyl-N′-ZnI3-1,4-diazabicyclo[2.2.2]octonium), with a record highTc(540 K) among molecular ferroelectrics, which is promising for application under extreme thermal conditions.

Effective neutralization of chemical warfare agents (HD, VX) by Me-DABCOF: A small molecule with dual action

The ability of mono N-methyl-1,4-diazabicyclo[2.2.2]octane fluoride (Me-DABCOF, 1) to act as a bifunctional reagent that effectively and universally neutralizes both the persistent and extremely toxic blister agent HD and the nerve agent VX in nearly neutral aqueous solution, alumina powder or a hydrogel formulation, is described.

Cell penetrating, mitochondria targeting multiply charged DABCO-cyanine dyes

We have prepared new series of lipophilic cyanine dyes equipped with several cationic quaternary ammonium moieties. This was achieved by introducing DABCO within the structures. Furthermore, to investigate the influence of the additional cationic charges on the cellular uptake, DABCO was quaternized with methyl group or alkyl piperidine cation. Spectroscopic and isothermal titration calorimetry studies as well as MTT assay and subcellular localization using confocal laser scanning microscopy revealed that some of the presented dyes combine low anti-proliferative effect with efficient cellular uptake, high affinity towards ds-DNA/RNA and remarkable fluorescent marking of mitochondria.

Remote halogen switch of amine hydrophilicity

Bromide and iodide anions switch hydrogen-bonding patterns in otherwise isostructural dimethanol solvates N-methyl-1,4-diazabicyclo[2.2.2]octanium bromide (dabcoCH3Br·2CH3OH) and analogous iodide (dabcoCH3I·2CH3OH), both synthesized in the high-pressure version of the Menshutkin reaction at 1.2 and 2.4 GPa, respectively. The magnitudes of the high pressure triggering these reactions correspond to identical molecular volumes of both solvates. This journal is

Simple and efficient synthesis of N-quaternary salts of quinuclidinium derivatives

The rapid and efficient synthesis of 1-alkylquinuclidinium (1-alkyl-1-azabicyclo[2.2.2]octane) and 1-alkyl-4-aza-1-azoniabicyclo[2.2.2] octane iodides are described. The products were characterized by 1H NMR spectra and elemental analysis. Georg Thieme Verlag Stuttgart.

peculiarities of C60- coordination to cobalt(II) octaethylporphyrin in ionic multicomponent complexes: Observation of the reversible formation of Co-C(C60-) coordination bonds

Ionic multicomponent complexes containing the C60 anion, cobalt(II) octaethylporphyrin (OEP), and the noncoordinating tetramethylphosphonium cation (TMP+), [(TMP+){Co 11OEP(C60-)}(C6H5CN) x-(C6H4Cl2)1-x] (x?0.75) (1), or the coordinating cation of N-methyldiazabicyclooctane (MDABCO+), [{(MDABCO+)CoIIOEP(C 60-)}(C6H5CN)x(C 6H4Cl2)1-x (x?0.67) (2), were obtained. Diamagnetic o-bonded {CoIIOEP(C60-)) units in 1 have the Co...C(C60) distance of 2.268(1) A at 100 K and are stable up to 290 K. Both MDABCO+ and C 60- coordinate to CoIIOEP in 2. In this case, a noticeably longer Co...C(C60-) distance of 2.508(4) A was observed at 100 K. As a result, the unprecedented reversible formation of the Co-C(C60-) coordination σ bond is realized in 2 and is accompanied by a transition from a paramagnetic to a diamagnetic state in the 50-250 K range. It was shown, for the first time, that the Co...C distance of about 2.51 A is a boundary distance below which the Co-C(C61-) coordination bond is formed.

Alkaline stability of quaternary ammonium cations for alkaline fuel cell membranes and ionic liquids

The alkaline stability of 26 different quaternary ammonium groups (QA) is investigated for temperatures up to 160°C and NaOH concentrations up to 10 molL-1 with the aim to provide a basis for the selection of functional groups for hydroxide exchange membranes in alkaline fuel cells and of ionic-liquid cations stable in basic conditions. Most QAs exhibit unexpectedly high alkaline stability with the exception of aromatic cations. b-Protons are found to be far less susceptible to nucleophilic attack than previously suggested, whereas the presence of benzyl groups, nearby hetero-atoms, or other electron-withdrawing species promote degradation reactions significantly. Cyclic QAs proved to be exceptionally stable, with the piperidine-based 6-azonia-spiro[5.5]undecane featuring the highest half-life at the chosen conditions. Absolute and relative stabilities presented herein stand in contrast to literature data, the differences being ascribed to solvent effects on degradation.

Above-Room-Temperature Ferroelastic Phase Transitions in Two Tetrafluoroborate-Based Hexagonal Molecular Perovskites

ABX3-type molecular perovskites provide an important platform to tune phase transitions, via judiciously choosing A-, B-, and X-site components, to approach advanced functional materials for applications. Although tetrafluoroborate can act as X-site component to assemble ten instances of ABX3 molecular perovskites, only two of them possess hexagonal perovskite structures. Herein, we report two tetrafluoroborate-based hexagonal molecular perovskites, A[Na(BF4)3], by judiciously choosing two different A-site cations: 1-methyl-1,4-diazabicyclo[2.2.2]octane-1,4-diium (Hmdabco2+) for 1 and 1-methylpiperazine-1,4-diium (H2mpz2+) for 2. They have high-temperature phases in the same space group (P63/mmc) revealing highly disordered A-site cations. Upon cooling, 1 undergoes two-step P63/mmc ? P3?c1 ? P21/n transitions at 344 and 338 K, respectively, including a ferroelastic one (3?mF2/m) accompanied by a spontaneous strain of 0.013. In contrast, the smaller H2mpz2+ cation with more adoptable conformations induces a one-step sharp P63/mmc ? P21/c ferroelastic transition (6/mmmF2/m(s)) at 418 K in 2, leading to more significant symmetry breaking and a considerable spontaneous strain of 0.129. This study provides important clues to modulate structural phase transitions by tuning diverse components for the multicomponent dense hybrid crystals.

Solid phase synthesis of metal-free perovskite crystalline materials

Metal-free perovskites, a new class of perovskite materials, show attractive piezoelectric, ferroelectric and pyroelectric properties because of their intrinsic structural properties. The introduction of organic components also leads to desirable properties such as structural adjustability, high mechanical flexibility, environmentally friendly processing conditions and low treatment temperatures. However, explorations of new metal-free perovskite materials suffer from the drawbacks of their previous liquid phase synthesis method, such as high time cost and poor experimental reproducibility. Here, we reported the first solid-phase synthesis of metal-free perovskite crystalline materials. Using the optimized ball milling method, we found that the starting materials were fully converted to pure metal-free perovskite DABCO-NH4Br3 (DABCO ?= ?N,N′-diazabicyclo [2.2.2] octonium) in the size of 5–10 ?μm. This solid phase synthesis strategy was successfully applied to the synthesis of MDABCO-NH4I3 (MDABCO ?= ?N-methyl-N′-diazabicyclo [2.2.2] octonium), demonstrating the great potential for the preparation and exploration of metal-free perovskite materials via solid phase synthesis.

Amination reagent as well as preparation method and application thereof

The invention discloses an amination reagent as well as a preparation method and application thereof. The amination reagent has a structure as shown in a formula disclosed in the invention, wherein Xis selected from any one of I, Cl, Br, NO3 and ClO4, and Y and Z are independently selected from H or alkyl with the carbon atom number of 1-4. The process for preparing the amination reagent is simple, the raw materials are easy to obtain, the cost is low, the yield is stable, and the prepared amination reagent is stable in character, can be stored at room temperature for a long time and can be taken as needed; meanwhile, the prepared amination reagent is efficient in performance, boron substrate applicability is excellent, reaction effect is good, and limitation of amination reaction of organic boron compounds on substrates is greatly expanded.