17739-45-6

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(2-Bromoethoxy)tetrahydro-2H-pyran is used as a key intermediate in the synthesis of various pharmaceutical compounds for their potential therapeutic applications.
Used in Chemical Research:
In the field of chemical research, 2-(2-Bromoethoxy)tetrahydro-2H-pyran serves as a valuable building block for the development of new chemical entities and the exploration of novel chemical reactions.
Used in Organic Synthesis:
2-(2-Bromoethoxy)tetrahydro-2H-pyran is utilized as a versatile reagent in organic synthesis for the preparation of a wide range of organic compounds.
Used in the Synthesis of 4-(2-chloroethoxy)benzenesulfonyl chloride:
2-(2-Bromoethoxy)tetrahydro-2H-pyran is used as a precursor in the synthesis of 4-(2-chloroethoxy)benzenesulfonyl chloride, which is an important chemical intermediate.
Used in the Synthesis of Estrogen Ligands Bearing Carborane:
This organic building block is employed in the synthesis of estrogen ligands bearing carborane, which are of interest in medicinal chemistry and drug development.
Used in the Synthesis of 2-(2-(1,3-di((E)-2-(2-(2-(2-(5-(4-(tert-butoxycarbonyl(methyl)amino)styryl)pyridin-2-yloxy)ethoxy)ethoxy)ethoxy)propan-2-yloxy)ethoxy)-tetrahydro-2H-pyran:
2-(2-Bromoethoxy)tetrahydro-2H-pyran is used as a starting material in the complex synthesis of a specific tetrahydro-2H-pyran derivative with potential applications in various fields.

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 540-51-2 2-bromoethanol 
• 144-55-8 sodium hydrogencarbonate 
• 141072-57-3 1-bromoethanol 
• 142-68-7 TETRAHYDROPYRANE 
• 627-18-9 1-bromo-3-propanol 
• 59134-92-8 4-trifluoroacetamidothiazole 

Downstream Products

• 138452-34-3 1-Phenyl-2-<2-(tetrahydropyranyloxy)ethyl>naphth<1,2,3-cd>indol-6(2H)-one 
• 159028-69-0 2-(2-((5-(benzyloxy)pentyl)oxy)ethoxy)tetrahydro-2H-pyran 
• 64841-44-7 5-<2'-(tetrahydropyranyloxy)>-1-pentene 
• 182802-99-9 5''-methyl-5-<3-<(tetrahydro-2H-pyran-2-yl)oxy>-1-propyl>-2,2':6',2''-terpyridine 
• 185347-49-3 α-(o-anisyl)-γ-butyrolactone 
• 191331-97-2 4-methoxyphenoxyethyl tetrahydro-2H-pyran-2-yl ether 
• 210552-35-5 (+)-(S)-N-(2-Hydroxyethyl)-S-methyl-3-phenylsulfoximine 
• 205381-47-1 2,4-dichlorophenoxyethyl tetrahydro-2H-pyran-2-yl ether 
• 205381-79-9 2-(4-benzylphenoxy)ethyl tetrahydro-2H-pyran-2-yl ether 
• 205381-75-5 4-benzyloxyphenoxyethyl tetrahydro-2H-pyran-2-yl ether 
• 205380-90-1 2-bromo-4-phenoxyphenoxyethyl tetrahydropyranyl ether 
• 205381-01-7 2-(2-chloro-4-phenoxyphenoxy)ethyl tetrahydro-2H-pyran-2-yl ether 
• 218146-25-9 1,3,5-tris[2-[2-(tetrahydropyran-2-yloxy)ethoxy]ethyl]benzene 
• 81183-58-6 1-bromo-4-[2-(2-tetrahydropyranyloxy)ethoxy]benzene 

Relevant academic research and scientific papers

Syntheses, characterizations, and biological activities of tetradeca-4,8-dien-1-yl acetates as sex attractants of leaf-mining moth of the genus Phyllonorycter (Lepidoptera: Gracillariidae)

The four possible isomers of tetradeca-4,8-dien-1-yl acetate and corresponding alcohols were synthesized stereoselectively by synthetic routes employing Wittig coupling reaction for the preparation of (Z,E)- and (Z,Z)-isomers, and alkylation of terminal alkynes for the preparation of (E,E)- and (E,Z)-isomers as the key steps. Synthetic products were characterized by 13C- and 1H-NMR spectroscopy as well as mass-spectrometric methods. All four isomers gave distinctive mass spectra where m/z 81 fragments clearly dominated. Elution order, followed by retention index presented in parenthesis, of tetradeca-4,8-dien-1-ols was determined as (Z,Z) (2082.1), (Z,E) (2082.8), (E,E) (2083.1), and (E,Z) (2083.2) from unpolar SPB-1 column, and as (E,E) (2210.2), (Z,E) (2222.1), (E,Z) (2223.4), and (Z,Z) (2224.7) from polar DB-WAX column. The isomers of tetradeca-4,8-dien-1-yl acetates eluted in the order of (Z,Z) (2176.1), (Z,E) (2178.4), (E,Z) (2185.9), and (E,E) (2186.4) from SPB-1, and (Z,E) (2124.3), (E,E) (2157.7), (Z,Z) (2128.9), and (E,Z) (2135.9) from DB-WAX columns. Field-screening tests for attractiveness of tetradeca-4,8-dien-1-yl acetates revealed that (4Z,8E)-tetradeca-4,8-dien-1-yl acetate significantly attracted Phyllonorycter coryli and Chrysoesthia drurella males. (4E,8E)-Tetradeca-4,8-dien-1-yl acetate was the most efficient attractant for Ph. esperella and Ph. saportella males, and (4E,8Z)-tetradeca-4,8-dien-1-yl acetate was attractive to Ph. cerasicolella males.

Competition between the β-hydroxylation of a primary and a tertiary carbon atom in rats

In order to study the effect of steric hindrance on competition between two kinds of β-hydroxylation, a compound bearing on a pyrimidinetrione nucleus both a branched side chain with a tertiary carbon atom in position β (isobutyl group) and a linear side chain (ethyl group), was selected and administered to rats. Urine and faeces were collected and extracted. Hydroxymetabolites and their derivatives were isolated and then identified. The β-hydroxylation of the linear chain was more important than the β-hydroxylation of the branched chain. Steric hindrance plays a decisive role in this regioselectivity.

Fluorene-containing polyhedral oligomericsilsesquioxanes modified hyperbranched polymer for white light-emitting diodes with ultra-high color rendering index of 96

In this work, a series of hyperbranched white-emitting conjugated polymers were synthesized with polyfluorene (PF) as the branches and three-dimensional-structured spiro[3.3]heptane-2,6-dispirofluorene (SDF) as the conjugated branching point by one-pot Suzuki polycondensation, where 4,7-dithienyl-2,1,3-benzothiadiazole (DBT) as orange-light emitting unit and fluorene-containing polyhedral oligomericsilsesquioxanes (POSSs) as conjugated linking monomer were introduced into the backbones to obtain white-light emission. The influence mechanism of POSSs for hyperbranched white-emitting polymers was explored by adjusting the feeding ratios of fluorene-containing POSSs (from 1 to 20 ?mol%). The results indicated that the synthesized polymers still maintained the high thermal stabilities, and exhibited the improved amorphous film morphology and hydrophobicity, which were beneficial for obtaining optimized interface between the aqueous hole transport layer Poly(3,4-ethylenedioxythiophene)-poly(styrenesulfonate) (PEDOT: PSS) layer and polymer light-emitting layer in device fabrication. As a consequence, all of the fabricated devices with the hyperbranched polymers as light-emitting layers realized white light-emission, and the optimized device exhibite good electroluminescent (EL) performance with Commission Internationale de l'Eclairage (CIE) coordinates at (0.32, 0.33) and maximum color rendering index (CRI) of 96. The fluorene-containing POSSs modified hyperbranched copolymers with broad full width at half maximum (>284 ?nm) are attractive candidates for sunlight-style white polymer light-emitting diodes.

Original electroactive and fluorescent bichromophores based on non-conjugated tetrazine and triphenylamine derivatives: Towards more efficient fluorescent switches

The synthesis, photophysical and electrochemical properties and their interplay as well as theoretical calculations studies of newly designed fluorescent and electroactive derivatives are described. These molecules are composed of two fluorophores: one triphenylamine, electron-rich unit, and one tetrazine, electron-poor unit, connected by two different links. While in the neutral state the bichromophores are not fluorescent, due to a photoinduced electron transfer from the triphenylamine unit to the tetrazine unit, the fluorescence is restored in the oxidative state (oxidation of the triphenylamine moiety).

An efficient synthesis of ω-(2,2′-bipyridyl)alkyl alcohols and their acrylates

ω-(2,2′-Bipyridyl)alkyl alcohols were synthesized by treatment of methyl-2,2′-bipyridine with LDA at -78°C followed by the addition of ω-bromoalkyl THP ether and hydrolysis of the resulting THP ether. Furthermore, ω-2,2′-bipyridylalkyl acrylates were obtained by the reaction of the corresponding ω-(2,2′-bipyridyl)alkyl alcohols with acryloyl chloride in good yields.

Towards an Improved Design of MRI Contrast Agents: Synthesis and Relaxometric Characterisation of Gd-HPDO3A Analogues

The properties of LnIII-HPDO3A complexes as relaxation enhancers and paraCEST agents are essentially related to the hydroxylpropyl moiety. A series of three HPDO3A derivatives, with small modifications to the hydroxyl arm, were herein investigated to understand how heightened control can be gained over the parameters involved in the design of these agents. A full 1H and 17O-NMR relaxometric analysis was conducted and demonstrated that increasing the length of the OH group from the lanthanide centre significantly enhanced the water exchange rate of the gadolinium complex, but with a subsequent reduction in kinetic stability. Alternatively, the introduction of an additional methyl group, which increased the steric bulk around the OH moiety, resulted in the formation of almost exclusively the TSAP isomer (95 %) as identified by 1H-NMR of the europium complex. The gadolinium analogue of this complex also exhibited a very fast water exchange rate, but with no detectable loss of kinetic stability. This complex therefore demonstrates a notable improvement over Gd-HPDO3A.

Synthesis and mesomorphic properties of some anthraquinone derivatives: New difunctionalised discotic monomers

Some new 9,10-anthraquinone (rufigallol) derivatives have been prepared and their mesomorphic properties have been studied. The unsymmetrically substituted tetrahydropyranyloxy-ethers (THP-ethers), exhibited columnar mesomorphism at fairly low temperatures and the xray studies carried out for one of the homologues confirmed the hexagonal nature of the mesophase. The deprotected derivatives of these THP-ethers, also form columnar mesophases. All these derivatives are very good candidates for polymerisation studies.

LIPID COMPOUNDS AND LIPID NANOPARTICLE COMPOSITIONS

Provided herein are lipid compounds that can be used in combination with other lipid components, such as neutral lipids, cholesterol and polymer conjugated lipids, to form lipid nanoparticles for delivery of therapeutic agents (e.g., nucleic acid molecules) for therapeutic or prophylactic purposes, including vaccination. Also provided herein are lipid nanoparticle compositions comprising said lipid compounds.

Development of high-affinity fluorinated ligands for cannabinoid subtype 2 receptor, and in vitro evaluation of a radioactive tracer for imaging

The development of neurodegenerative diseases is associated with cerebral inflammation, which activates resident immune cells of the central nervous system (CNS), namely microglial cells that show an up-regulation of the cannabinoid subtype 2 receptor (CB2R) expression. Therefore our work aimed to design and synthesize a radiotracer for the detection of CB2R expression by positron emission tomography (PET) allowing an early diagnosis of neurodegenerative diseases. For the development of such a PET tracer, N-alkyl-substituted indole-3-yl-tetramethylcyclopropylketones served as lead structures due to their high CB2R potency and selectivity, allowing radiolabeling on the N-alkyl chain. To this end, eight novel fluorinated N-alkyl-indole-3-yl-tetramethylcyclopropylketones were synthesized, investigated in radioligand binding studies, and structure-activity relationships were evaluated. The most promising candidate was (1-(4-fluoropropyl)-1H-indole-3-yl)(2,2,3,3-tetramethyl-cyclopropyl)methanone (Ki: 7.88 nM at the CB2R, 3430 nM at cannabinoid subtype 1 receptor (CB1R)). A precursor was synthesized, radiofluorinated with no-carrier-added [18F]F? by nucleophilic substitution of a tosyl group, and the resulting PET ligand was purified, all being performed on a fully automated synthesis module. The tracer was produced in 34 ± 6% radiochemical yield within 2 h and with molar activities of up to 1500 GBq/μmol. A first preclinical evaluation was carried out including determination of logP, metabolic stability by liver microsomes, and autoradiography. The novel PET tracer for imaging CB2R showed promising results warranting subsequent clinical evaluation.

INDAZOLE BASED COMPOUNDS AND ASSOCIATED METHODS OF USE

Bifunctional compounds, which find utility as modulators of leucine-rich repeat kinase 2 (LRRK2), are described herein. In particular, the hetero-bifunctional compounds of the present disclosure contain on one end a moiety that binds to the cereblon E3 ubiquitin ligase and on the other end a moiety which binds LRRK2, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The hetero-bifunctional compounds of the present disclosure exhibit a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aberrant regulation of the target protein are treated or prevented with compounds and compositions of the present disclosure.