1191-87-3

Usage

Uses

Used in Chemistry:
2,5,8,11,14,17-Hexaoxaoctadecane is used as a phase transfer catalyst for facilitating reactions between organic and inorganic compounds, as well as in ion-selective electrodes for the detection and measurement of specific metal ions.
Used in Supramolecular Chemistry:
2,5,8,11,14,17-Hexaoxaoctadecane is used as a building block in supramolecular chemistry for the construction of complex molecular structures and assemblies through non-covalent interactions.
Used in Ion-Exchange Chromatography:
2,5,8,11,14,17-Hexaoxaoctadecane is used as a stationary phase in ion-exchange chromatography for the separation and purification of metal ions based on their affinity to the crown ether.
Used in Drug Delivery Systems:
2,5,8,11,14,17-Hexaoxaoctadecane is used as a potential drug delivery agent for encapsulating cations, which can improve the solubility, stability, and bioavailability of therapeutic agents.

InChI:InChI=1/C12H26O6/c1-13-3-5-15-7-9-17-11-12-18-10-8-16-6-4-14-2/h3-12H2,1-2H3

Upstream product

• 109-86-4 2-methoxy-ethanol 
• 31255-10-4 1,2-bis-(2-bromo-ethoxy)-ethane 
• 23778-52-1 3,6,9,12,15-pentaoxahexadecanol 
• 77-78-1 dimethyl sulfate 
• 4792-15-8 Pentaethylene glycol 
• 74-88-4 methyl iodide 
• 17454-53-4 cyclohexano-18-crown-6 
• 112-26-5 1,2-bis(2-chloroethoxy)ethane 
• 112-27-6 2,2'-[1,2-ethanediylbis(oxy)]bisethanol 
• 75-21-8 oxirane 
• 115-10-6 Dimethyl ether 
• 112-35-6 triethylene glucol monomethyl ether 
• 19249-03-7 triethylene glycol di-(p-toluenesulfonate) 
• 111-77-3 2-(2-methoxyethoxy)ethyl alcohol 

Relevant academic research and scientific papers

Effects of hydration on the thermodynamic properties of aqueous ethylene glycol ether solutions

The densities and isobaric specific heat capacities of binary mixtures of water with various open-chain and cyclic ethylene glycol ethers have been measured at 298.15 K using vibrating tube densimetry, and flow or differential scanning calorimetry, respectively. Excess molar volumes were derived over the whole composition range. Molar isobaric heat capacities and the relative apparent thermodynamic quantities were determined in the water-rich region. The data reflect the changes in the structure and hydrogen-bond dynamics of water caused by these non-ionic solutes. The observed effects are discussed in terms of the influence of hydrophobic hydration on the thermodynamic properties of aqueous solutions. Correlations are given that enable the prediction of the thermodynamic properties of open-chain and cyclic oligo(ethylene oxide) ethers in their pure liquid state and at infinite dilution in water.

Ring-contracted Crown Ethers: 14-Crown-5, 17-Crown-6, and Their Sila-analogues. Drastic Decrease in Cation-binding Ability

As compared with symmetrical 3m-crown-m, the ring-contracted(3m-1)-crown-m showed drastic decrease in cation-binding ability, which is attributable not to the diminished cavity size but to the disordered conformation induced by ring contraction.

Molecular Design of Crown Ethers. 1. Effects of Methylene Chain Length: 15- to 17-Crown-5 and 18- to 22-Crown-6

The ring-enlarged crown ethers, 16- and 17-crown-5 and 19- to 22-crown-6, were synthesized and their cation-binding abilities were evaluated by solvent extraction of aqueous alkali metal picrates.The cation-binding abilities of less symmetrical crown ethers, 3a-e and 4a,b, were generally lower than those of the common symmetrical crown ethers 15-crown-5 (5a) and 18-crown-6 (5b), for which the less symmetrical arrangement of the donor oxygen atoms must be responsible.Compared with 18-crown-6 (5b), the ring-extended crown ethers, 3d, 3e, and 4b, showed a significant shift in cation selectivity, probably due to the enlarged cavity size.The thermodynamic parameters for the extraction of sodium and potassium picrates with 3a, 3c, and 5a,b were calculated from the change of the extraction equilibrium constants (Kex) between 10-25 deg C.The stability of the cation-crown ether complexes was shown to be governed in general by the enthalpy change.However, a significant contribution of the entropy factor was found in unfavorable size combinations of K+ with 3a and Na+ with 3c.

METHOD FOR PRODUCING ALKYLENE GLYCOL DIETHERS

The invention concerns a method for producing alkylene glycol diethers by reacting a linear or cyclic ether with an alkylene oxide in the presence of a Lewis acid. The invention is characterized in that the reaction is continuously carried out in a microreactor.

Preparation and decomposition of potassium alkalide-lipophilic crown ether complexes in tetrahydrofuran

Cyclohexano-15-crown-5, cyclohexano-18-crown-6, dicyclohexano-15-crown-5, and dicyclohexano-18-crown-6, but not dicylohexano-16-crown-5, in THF dissolve potassium metal to form dark blue potassium alkalide solutions at ambient temperature. On standing, the potassium alkalide complexes decompose and the solutions turn colorless at differing rates. Identification of the products provides insight into the decomposition mechanism.

Investigations on the influence of 2'-O-alkyl modifications on the base pairing properties of oligonucleotides

The antisense strategy has gained wide acceptance as a promising drug development concept. Antisense drugs hybridize with selected complementary sequences in a highly specific manner. However, as a main prerequisite for extensive therapeutic use of this new class of drugs, selected structural modifications are required to adjust pharmacokinetic and pharmacodynamic behavior. In continuation of our earlier investigations on 2'-O-modified oligonucleotides (Gotten, M., Oberhauser, B., Brunar, H., Holzner, A., Issakides, G., Noe, C.R., Schaffer, G., Wagner, E., Bimstiel, M.L., 1991. 2'-O-methyl, 2'-O-ethyl oligoribonucleotides and phosphorothioate oligodeoxyribonucleotides as inhibitors of the in vitro U7 snRNP-dependent mRNA processing event. Nucleic Acids Res. 19, 2629-2635; Wagner, E., Oberhauser, B., Holzner, A., Brunar, H., Issakides, G., Schaffner, G., Gotten, M., Knollmuller, M., Noe, C.R., 1991. A simple procedure for the preparation of protected 2'-O-methyl or 2'-O-ethyl ribonucleoside-3'-O-phosphoramidites. Nucleic Acids Res. 19, 5965-5971) further series of modified oligonucleotides containing different modified 2'-O-adenosines have been synthesized. On the one hand linear alkyl moieties of increasing length, on the other hand oxyethylene moieties of corresponding length were introduced at the 2'-O-position of adenosine. Following another approach a cationic charge was introduced by insertion of an aminohexylmodification at the 2'-O-position of adenosine (Brunar, H., Haberhauer, G., Werner, D., Noe, C.R., 1994. 2'-O-Modified oligonucleotides: Synthesis and biophysical analysis. Eur. J. Pharm. Sci. 2, 150). Molecule dynamics simulations had shown that this cationic modification upon duplex formation leads to both intra- and interstrand interactions. To determine the influence of the different modifications, such as cationic charge, alkyl chainlength and introduction of oxygen into the chain, on duplex stability melting temperatures were measured by recording circular dichroism versus temperature.

Hydrogenolysis and One-Electron Reduction of Alkoxy Sulfones

The readily available 1-t-butoxyalkyl sulfones were converted by hydride reduction into alkyl t-butyl ethers.Reductive coupling with sodium metal or amalgam in an aprotic solvent led to glycol bis-1,2-O-t-butyl ethers.Polyethers such as 18-crown-6 can be synthesized by this procedure.

Artificial allosteric receptors for nucleotide bases and alkali-metal cations

New allosteric thymine receptors, 2,6-diamidopyridine derivatives tethered to an anthracene ring by a polyoxyethylene chain, were synthesized. In these receptors, binding of 1-butylthymine was enhanced by a factor of 4-6 by recognition of sodium cations, and the changes in the electron density of the anthracene ring were found to have influence on the allosterism by through-space interaction. The anthracene-linked diamidopyridines represent a rationally designed new class of artificial allosteric receptors.

Structural Requirements for Glyme Catalysis in Butylaminolysis of Aryl Acetates in Chlorobenzene. Identification of -OCH2CH2OCH2CH2OCH2CH2O- as the Optimal Subunit for Catalysis

The catalytic behavior of linear (open-chain) polyethers (glymes) in butylaminolysis of 4-nitrophenyl acetate carried out in chlorobenzene has been reexamined (J.Am.Chem.Soc. 1980, 102, 2865-2866).The observation of a break in a plot of the catalytic rate constant vs chain length indicates that four oxygens in a -OCH2CH2OCH2CH2OCH2CH2O- subunit are necessary for optimal catalysis.The break, occuring at four oxygens in the profile (corresponds to triglyme), has been verified by a Hammett analysis, which employed four additional aryl acetates (3-chlorophenyl, 3-bromphenyl, 3-cyanophenyl, and 4-cyanophenyl).This break was missed in a previous study (J.Am.Chem.Soc. 1980, 102, 2865-2866) because differing amounts of impurities in the glymes increased the experimental scatter of the data.The Hammett study supports the conclusions of others that breakdown of the zwitterionic tetrahedral intermediate is rate-limiting.The break in the polyether plot implies a specific structure for a glyme-zwitterionic tetrahedral intermediate complex, which contains an ammonium ion that hydrogen bonds to the ether oxygens.

AFFINITIES OF CROWN ETHERS, GLYMES, AND POLYAMINES FOR ALKALI PICRATES IN TOLUENE. APPLICATION OF POLYMER-SUPPORTED LINEAR POLYETHERS.

This work reports the measurements of K values for polyamines, glymes, a few glycols (including that of a long-chain polyethylene glycol, carbowax 6000), and some frequently used cation-binding ligands as complexers of lithium or sodium picrate in toluene as solvent. K values for different resins obtained with the same soluble ligand provide a comparison of the effectiveness of these resins in binding ionic solutes.