124388-97-2

Upstream product

• 55362-80-6 9-bromononan-1-ol 

Downstream Products

• 876143-55-4 5-[(R)-2-[benzyl-(9-bromononyl)amino]-1-(tert-butyldimethylsilanyloxy)ethyl]-8-benzyloxy-1H-quinolin-2-one 
• 1416069-35-6 benzyl 3-((8-(1,3-dioxolan-2-yl)octyl)oxy)-5-bromobenzoate 
• 1416069-36-7 (3-((8-(1,3-dioxolan-2-yl)octyl)oxy)-5-bromophenyl)methanol 
• 1416069-37-8 3-((8-(1,3-dioxolan-2-yl)octyl)oxy)-5-bromobenzaldehyde 
• 1416069-46-9 (3-((8-(1,3-dioxolan-2-yl)octyl)oxy)-4-methylphenyl)-methanol 
• 1416069-18-5 (3-(8-(1,3-dioxolan-2-yl)octyloxy)phenyl)(phenyl)methanone 
• 1416069-19-6 (3-(8-(1,3-dioxolan-2-yl)octyloxy)phenyl)(phenyl)methanol 
• 1416069-20-9 2-(8-(3-(azido(phenyl)methyl)phenoxy)octyl)-1,3-dioxolane 
• 1416069-21-0 (3-(8-(1,3-dioxolan-2-yl)octyloxy)phenyl)(phenyl)methanamine 
• 1416069-22-1 (R)-quinuclidin-3-yl (3-(8-(1,3-dioxolan-2-yl)octyloxy)phenyl)(phenyl)methylcarbamate 
• 1416069-23-2 (R)-quinuclidin-3-yl (3-(9-oxononyloxy)phenyl)(phenyl)-methylcarbamate 
• 1416065-91-2 (R)-quinuclidin-3-yl (3-(9-((R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethylamino)nonyloxy)phenyl)-(phenyl)methylcarbamate 
• 1416069-24-3 3-(8-(1,3-dioxolan-2-yl)octyloxy)benzaldehyde 
• 1416069-25-4 (3-(8-(1,3-dioxolan-2-yl)octyloxy)phenyl)(thiophen-2-yl)methanol 

Relevant academic research and scientific papers

Nickel-Catalyzed Alkyl-Alkyl Cross-Couplings of Fluorinated Secondary Electrophiles: A General Approach to the Synthesis of Compounds having a Perfluoroalkyl Substituent

Fluorinated organic molecules are of interest in fields ranging from medicinal chemistry to polymer science. Described herein is a mild, convenient, and versatile method for the synthesis of compounds bearing a perfluoroalkyl group attached to a tertiary carbon atom by using an alkyl-alkyl cross-coupling. A nickel catalyst derived from NiCl2 glyme and a pybox ligand achieves the coupling of a wide range of fluorinated alkyl halides with alkylzinc reagents at room temperature. A broad array of functional groups is compatible with the reaction conditions, and highly selective couplings can be achieved on the basis of differing levels of fluorination. A mechanistic investigation has established that the presence of 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO) inhibits cross-coupling under these conditions and that a TEMPO-electrophile adduct can be isolated.

"ene" Reactions of Singlet Oxygen at the Air-Water Interface

Prenylsurfactants [(CH3)2C=CH(CH2)nSO3- Na+ (n = 4, 6, or 8)] were designed to probe the "ene" reaction mechanism of singlet oxygen at the air-water interface. Increasing the number of carbon atoms in the hydrophobic chain caused an increase in the regioselectivity for a secondary rather than tertiary surfactant hydroperoxide, arguing for an orthogonal alkene on water. The use of water, deuterium oxide, and H2O/D2O mixtures helped to distinguish mechanistic alternatives to homogeneous solution conditions that include dewetting of the π bond and an unsymmetrical perepoxide transition state in the hydroperoxide-forming step. The prenylsurfactants and a photoreactor technique allowed a certain degree of interfacial control of the hydroperoxidation reaction on a liquid support, where the oxidant (airborne 1O2) is delivered as a gas.

Design, synthesis of symmetrical bivalent mimetics of annonaceous acetogenins and their cytotoxicities

A new series of linear dimeric compounds mimicking naturally occurring annonaceous acetogenins have been synthesized by bivalent analogue design, and their cytotoxicities have been evaluated against the growth of cancer cells by MTT method. Most of these compounds show selective action favored to human cancer cell lines over normal cell lines, and compound 9 with bis-terminal benzoquinone functionality exhibits an IC50 = 0.40 μM against MCF7 cell lines. This work mentions that appropriate conformational constraints might be a useful optimizing tool for this unique class of anticancer compounds.

Discovery of a novel class of inhaled dual pharmacology muscarinic antagonist and β2 agonist (MABA) for the treatment of chronic obstructive pulmonary disease (COPD)

The targeting of both the muscarinic and β-adrenergic pathways is a well validated therapeutic approach for the treatment of chronic obstructive pulmonary disease (COPD). In this communication we report our effort to incorporate two pharmacologies into a single chemical entity, whose characteristic must be suitable for a once daily inhaled administration. Contextually, we aimed at a locally acting therapy with limited systemic absorption to minimize side effects. Our lung-tailored design of bifunctional compounds that combine the muscarinic and β-adrenergic pharmacologies by the elaboration of the muscarinic inhibitor 7, successfully led to the potent, pharmacologically balanced muscarinic antagonist and β2 agonist (MABA) 13.

Method for synthesizing (9Z, 12E)-9,12-tetradecadien-1-ol acetate

The invention belongs to the technical field of green pesticide synthesis, and discloses a novel method for synthesizing (9Z, 12E)-9,12-tetradecadien-1-ol acetate. According to the method, malonic acid and 9-bromo-1-nonyl alcohol are used as two starting raw materials. The method comprises the following steps: carrying out a Knoevenagel condensation reaction on malonic acid and propionaldehyde inthe presence of piperidine acetate to generate (E)-3-pentenoic acid, then carrying out lithium aluminum hydride reduction to obtain (E)-3-penten-1-ol, carrying out bromination reaction, and refluxingwith triphenylphosphine in acetonitrile to obtain (E)-3-pentenyltriphenylphosphine bromide; carrying out a PCC oxidation reaction on 9-bromo-1-nonanol to obtain 9-bromononanal, and then reacting the 9-bromononanal with potassium acetate to obtain 9-acetoxynonanal; and finally, carrying out a Wittig reaction on (E)-3-pentenyltriphenylphosphine bromide and 9-acetoxynonanal so as to obtain (9Z, 12E)-9,12-tetradecadien-1-ol acetate. An E-type double bond is constructed by utilizing the Knoevenagel condensation reaction of malonic acid and propionaldehyde, and the method has the advantages of mildreaction conditions, environmental friendliness, simple synthetic route and the like.

Unprecedented Selectivity of Ruthenium Iodide Benzylidenes in Olefin Metathesis Reactions

The development of selective olefin metathesis catalysts is crucial to achieving new synthetic pathways. Herein, we show that cis-diiodo/sulfur-chelated ruthenium benzylidenes do not react with strained cycloalkenes and internal olefins, but can effectively catalyze metathesis reactions of terminal dienes. Surprisingly, internal olefins may partake in olefin metathesis reactions once the ruthenium methylidene intermediate has been generated. This unexpected behavior allows the facile formation of strained cis-cyclooctene by the RCM reaction of 1,9-undecadiene. Moreover, cis-1,4-polybutadiene may be transformed into small cyclic molecules, including its smallest precursor, 1,5-cyclooctadiene, by the use of this novel sequence. Norbornenes, including the reactive dicyclopentadiene (DCPD), remain unscathed even in the presence of terminal olefin substrates as they are too bulky to approach the diiodo ruthenium methylidene. The experimental results are accompanied by thorough DFT calculations.

BIODEGRADABLE LIPIDS FOR THE DELIVERY OF ACTIVE AGENTS

The present invention relates to a cationic lipid having one or more biodegradable groups located in a lipidic moiety (e.g., a hydrophobic chain) of the cationic lipid. These cationic lipids may be incorporated into a lipid particle for delivering an active agent, such as a nucleic acid. The invention also relates to lipid particles comprising a neutral lipid, a lipid capable of reducing aggregation, a cationic lipid of the present invention, and optionally, a sterol. The lipid particle may further include a therapeutic agent such as a nucleic acid.

Fluorinated triazole-containing sphingosine analogues. Syntheses and in vitro evaluation as SPHK inhibitors

Sphingosine analogues with a rigid triazole moiety in the aliphatic chain and systematic modifications in the polar head and different degrees of fluorination at the terminus of the alkylic chain were synthesized from a common alkynyl aziridine key synthon. This key synthon was obtained by enantioselective organocatalyzed aziridination and it was subsequently ring opened in a regioselective manner in acidic medium. Up to 16 sphingosine analogues were prepared in a straightforward manner. The in vitro activity of the obtained products as SPHK1 and SPHK2 inhibitors was evaluated, displaying comparable activity to that of DMS.

Stereoconvergent negishi arylations of racemic secondary alkyl electrophiles: Differentiating between a CF3 and an alkyl group

In this report, we establish that a readily available nickel/bis(oxazoline) catalyst accomplishes a wide array of enantioconvergent cross-couplings of arylzinc reagents with CF3-substituted racemic secondary alkyl halides, a process that necessitates that the chiral catalyst be able to effectively distinguish between a CF3 and an alkyl group in order to provide good ee. We further demonstrate that this method can be applied without modification to the catalytic asymmetric synthesis of other families of fluorinated organic compounds.

COMPOUNDS HAVING MUSCARINIC RECEPTOR ANTAGONIST AND BETA2 ADRENERGIC RECEPTOR AGONIST ACTIVITY

Compounds of formula (I) act both as muscarinic receptor antagonists and beta2 adrenergic receptor agonists and are useful for treating and/or preventing broncho-obstructive and inflammatory diseases.