2‐Cyclohexyloxyethanol

Daignault, Ronald A.; Eliel, Ernest L.

doi:10.1002/0471264180.os047.10

Cited by 7 publications

(7 citation statements)

References 6 publications

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“…The acid-catalyzed acetalization of aldehydes and ketones with diols is one of the most common transformations in organic synthesis (see Supporting Information for further details); we modified previously reported methods for the formation of acetals and ketals starting from carbonyl compounds (Scheme ). − The derivatization reaction was carried out by adding 20 μL of BF 3 and 50 μL of 0.1 mM ( S , S )-DMB-Diol to the DCM meteorite extract and heating the mixture at 110 °C for 1 h in sealed glass vials with PFTE-lined screw caps. Then, the reacted solution was concentrated to ∼1 mL by flowing nitrogen gas (N 2 ) and extracted using 1 mL of water three times to remove the unreacted ( S , S )-DMB-Diol and BF 3 .…”

Section: Methodsmentioning

confidence: 99%

Analyses of Aliphatic Aldehydes and Ketones in Carbonaceous Chondrites

Aponte

Whitaker

Powner

et al. 2019

ACS Earth Space Chem.

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Aliphatic aldehydes and ketones are essential building blocks for the synthesis of more complex organic compounds. In spite of their potentially key role as precursors of astrobiologically-important molecules, such as amino acids and carboxylic acids, this family of compounds has scarcely been evaluated in carbonaceous chondrites. The paucity of such analyses likely derives from the low concentration of aldehydes and ketones in the meteorites, and from the currently used chromatographic methodologies that have not been optimized for meteorite analysis. In this work, we report the development of a novel analytical method to quantify the molecular distribution and compound-specific isotopic analysis of 29 aliphatic aldehydes and ketones. Using this method, we have investigated the molecular distribution and 13 C-isotopic composition of aldehydes and ketones in ten carbonaceous chondrites from the CI, CM, CR and CV groups. The total concentration of carbonyl compounds ranged from 130 to 1000 nmolg-1 of meteorite, with formaldehyde, acetaldehyde, and acetone being the most abundant species in all investigated samples. The 13 C-isotopic values ranged from-67 to +64‰ and we did not observe clear relationships between 13 C-content and molecular weight. Accurately measuring the relative abundances, determining the molecular distribution, and isotopic composition of chondritic organic compounds is central in assessing both their formation chemistry and synthetic relationships.

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Section: Methodsmentioning

confidence: 99%

Analyses of Aliphatic Aldehydes and Ketones in Carbonaceous Chondrites

Aponte

Whitaker

Powner

et al. 2019

ACS Earth Space Chem.

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“…The furan also interactsw ith the side diamine residues( localised to the minor groove) further stabilising the complexes by van der Waals and coulombic interactions. [86] Dioxolane is a heterocyclic acetal with the chemical formula (CH 2 ) 2 O 2 CH 2 .I ti s related to tetrahydrofuran by the interchange of aC H 2 group for one oxygen atom. [83] In 2016, Cui et al reported the synthesis of 2,5-disubstituted 1,3,4-thiadiazole derivatives of 5-phenyl-2-furan using Lawesson's reagent under microwavei rradiation anda lso evaluated their fungicidal activity.T hese compounds showedc onsiderable inhibitory potential against five selected fungi, especially with Phytophthora infestans.…”

Section: Pharmacological Profile Of Furan Derivativesmentioning

confidence: 99%

The Current Status of O‐Heterocycles: A Synthetic and Medicinal Overview

Singh

Silakari

2018

ChemMedChem

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O-Heterocycles have been explored in the field of medicinal chemistry for a long time, but their significance has not been duly recognised and they are often shunned in favour of N-heterocycles. The design of bioactive molecules for nearly every pathophysiological condition is primarily focused on novel N-heterocycles. The main reasons for such bias include the ease of synthesis and possible mimicking of physiological molecules by N-heterocycles. But considering only this criterion rarely provides breakthrough molecules for a given disease condition, and instead the risks of toxicity or side effects are increased with such molecules. On the other hand, owing to improved synthetic feasibility, O-heterocycles have established themselves as equally potent lead molecules for a wide range of pathophysiological conditions. In the last decade there have been hundreds of reports validating the fact that equally potent molecules can be designed and developed by using O-heterocycles, and these are also expected to have comparably low toxicity. Even so, researchers tend to remain biased toward the use of N-heterocycles over O-heterocycles. Thus, this review provides a critical analysis of the synthesis and medicinal attributes of O-heterocycles, such as pyrones, oxazolones, furanones, oxetanes, oxazolidinones, and dioxolonones, and others, reported in the last five years, underlining the need for and the advantages guiding researchers toward them.

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“…Procedure A was used with 2-(4-bromophenyl)-2-methyl-1,3-dioxane (256 mg, 1 mmol), mebynol (0.2 mL, 2 mmol), DIPA (0.5 mL, 3 mmol), copper(I) iodide (22 mg, 0.1 mmol), triphenylphosphine (75 mg, 0.3 mmol), and palladium(II) acetate (12 mg, 0.05 mmol) (time = 2 h; eluent = ether/ethyl acetate, 10:1) to give product 2-methyl-4-(4-(2-methyl-1,3-dioxolan-2-yl)phenyl)but-3-yn-2-ol (170 mg, 86%) as yellow crystals: mp 70.5–71.5 °C. 1 H NMR (CDCl 3 , 500 MHz): δ (ppm) 7.47–7.33 (m, 4H), 4.13–3.61 (m, 4H), 2.11 (s, 1H, H10), 1.64 (s, 3H), 1.62 (s, 6H).…”

Section: Methodsmentioning

confidence: 99%

Design, Syntheses, and in Vitro Evaluation of New Fluorine-18 Radiolabeled Tau-Labeling Molecular Probes

et al. 2017

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Deposition of aggregates of hyperphosphorylated tau protein is a hallmark of tauopathies like Alzheimer and many other neurodegenerative diseases. A sensitive and selective method of in vivo detection of tau-aggregate presence and distribution could provide the means of an early diagnosis of tau-associated diseases. Furthermore, the use of selective molecular probes that enable histochemical differentiation of protein aggregates post-mortem would be advantageous for the insight into the properties of tau protein aggregates. We chose to design new molecular probes based on the structure of 2-(1-(6-((2-[F]fluoroethyl)(methyl)amino)-2-naphthyl)ethylidene)malononitrile to investigate their likelihood of fitting into VQIVYK tau protein binding channel model. In a modular approach, using cross-coupling reactions, we synthesized a series of candidates, radiolabeled them with fluorine-18 radioisotope, and determined their physicochemical and in vitro binding properties. Herein we report the synthesis of a series of molecular probes capable of detection of tau protein deposits in vitro.

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2‐Cyclohexyloxyethanol

Abstract: 2‐Cyclohexyloxyethanol intermediate: 1,4‐Dioxaspiro[4.5]decane product: 2‐Cyclohexyloxyethanol

Cited by 7 publications

References 6 publications

Analyses of Aliphatic Aldehydes and Ketones in Carbonaceous Chondrites

Analyses of Aliphatic Aldehydes and Ketones in Carbonaceous Chondrites

The Current Status of O‐Heterocycles: A Synthetic and Medicinal Overview

Design, Syntheses, and in Vitro Evaluation of New Fluorine-18 Radiolabeled Tau-Labeling Molecular Probes

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