106262-52-6

Upstream product

• 112-38-9 10-undecenoic acid 
• 100-51-6 benzyl alcohol 
• 111-81-9 Methyl 10-undecenoate 
• 100-39-0 benzyl bromide 
• 18508-59-3 phenyl 10-undecenoate 
• 134781-62-7 2,4,6-Trichlorobenzoic 10-undecenoic anhydride 
• 134781-63-8 S-pyridin-2-yl 10-undecenethioate 

Downstream Products

• 67853-00-3 benzyl 10-hydroxydecanoate 
• 64273-11-6 benzyl undecanoate 
• 380228-17-1 11-hydroxyundecanoic acid benzyl ester 
• 1035222-27-5 C₂₄H₄₂O₅Si 
• 1446088-17-0 C₁₉H₃₀O₃ 
• 1446088-18-1 C₂₂H₃₆O₃ 
• 1602485-31-3 C₁₉H₂₆F₃N₃O₂ 
• 129266-47-3 benzyl hept-6-enoate 

Relevant academic research and scientific papers

Efficient Synthesis of Cyclic Carbonates from Unsaturated Acids and Carbon Dioxide and their Application in the Synthesis of Biobased Polyurethanes

Bio-derived furan- and diacid-derived cyclic carbonates have been synthesized in high yields from terminal epoxides and CO2. Furthermore, four highly substituted terpene-derived cyclic carbonates were isolated in good yields with excellent diastereoselectivity in some cases. Eleven new cyclic carbonates derived from 10-undecenoic acid under mild reaction conditions were prepared, providing the corresponding carbonate products in excellent yields. The catalyst system also performed the conversion of an epoxidized fatty acid n-pentyl ester into a cyclic carbonate under relatively mild reaction conditions (80 °C, 20 bar, 24 h). This bis(cyclic carbonate) was obtained in high yields and with different cis/trans ratios depending on the co-catalyst used. An allyl alcohol by-product was only observed as a minor product when bis(triphenylphosphine)iminium chloride was used as co-catalyst. Finally, two cyclic carbonates were used as building blocks for the preparation of non-isocyanate poly(hydroxy)urethanes by reaction with 1,4-diaminobutane.

Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones

The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.

Methyl Radical Initiated Kharasch and Related Reactions

An improved procedure to run halogen atom and related chalcogen group transfer radical additions is reported. The procedure relies on the thermal decomposition of di-tert-butylhyponitrite (DTBHN), a safer alternative to the explosive diacetyl peroxide, to produce highly reactive methyl radicals that can initiate the chain process. This mode of initiation generates byproducts that are either gaseous (N2) or volatile (acetone and methyl halide) thereby facilitating greatly product purification by either flash column chromatography or distillation. In addition, remarkably simple and mild reaction conditions (refluxing EtOAc during 30 minutes under normal atmosphere) and a low excess of the radical precursor reagent (2 equivalents) make this protocol particularly attractive for preparative synthetic applications. This initiation procedure has been demonstrated with a broad scope since it works efficiently to add a range of electrophilic radicals generated from iodides, bromides, selenides and xanthates over a range of unactivated terminal alkenes. A diverse set of radical trap substrates exemplifies a broad functional group tolerance. Finally, di-tert-butyl peroxyoxalate (DTBPO) is also demonstrated as alternative source of tert-butoxyl radicals to initiate these reactions under identical conditions which gives gaseous by-products (CO2). (Figure presented.).

Cyclopropanation of Terminal Alkenes through Sequential Atom-Transfer Radical Addition/1,3-Elimination

An operationally simple method to affect an atom-transfer radical addition of commercially available ICH2Bpin to terminal alkenes has been developed. The intermediate iodide can be transformed in a one-pot process into the corresponding cyclopropane upon treatment with a fluoride source. This method is highly selective for the cyclopropanation of unactivated terminal alkenes over non-terminal alkenes and electron-deficient alkenes. Due to the mildness of the procedure, a wide range of functional groups such as esters, amides, alcohols, ketones, and vinylic cyclopropanes are well tolerated.

Fluorine-containing carboxylic acid compound

PROBLEM TO BE SOLVED: To provide a fluorinated carbon group-containing carboxylic acid that is dissolved in organic solvent, has excellent surface tension reduction ability, and has a small number of carbon atoms, and a surfactant. SOLUTION: The present i

Base catalyzed sustainable synthesis of phenyl esters from carboxylic acids using diphenyl carbonate

Phenyl esters were obtained in moderate to high yields by reaction of aliphatic and aromatic carboxylic acids with one equivalent of diphenyl carbonate in the presence of catalytic amounts of tertiary amine bases, such as DBU, TBD and DMAP under neat conditions at elevated temperatures (>100°C).

Hydroalkoxylation of unactivated olefins with carbon radicals and carbocation species as key intermediates

A unique Markovnikov hydroalkoxylation of unactivated olefins with a cobalt complex, silane, and N-fluoropyridinium salt is reported. Further optimization of reaction conditions yielded high functional group tolerance and versatility of alcoholic solvent employed, including methanol, i-propanol, and t-butanol. Use of trifluorotoluene as a solvent made the use of alcohol in stoichiometric amount possible. Mechanistic insight into this novel catalytic system is also discussed. Experimental results suggest that catalysis involves both carbon radical and carbocation intermediates.

5,5′-Dimethyl-3,3′-azoisoxazole as a new heterogeneous azo reagent for esterification of phenols and selective esterification of benzylic alcohols under Mitsunobu conditions

5,5′-Dimethyl-3,3′-azoisoxazole is used as a new efficient heterogeneous azo reagent for the highly selective esterification of primary and secondary benzylic alcohols and phenols with aliphatic and aromatic carboxylic acids via Mitsunobu protocols. The reaction is highly selective for primary benzylic alcohols versus secondary ones, aliphatic alcohols and also phenols. The isoxazole hydrazine byproduct can be simply isolated by filtration and recycled to its azoisoxazole by oxidation.

From simple molecules to highly functionalised lamellar materials

We describe here a new method permitting the one-step synthesis of ordered (lamellar phase) organosilicas highly functionalised with carboxylic acid or phosphonic acid groups. These materials were obtained by hydrolysis and polycondensation of monosilylated precursors cyanoalkyltrialkoxysilane (NC-(CH2)nSi(OR)3) and diethylphosphonatoalkyltriethoxysilane ((EtO)2(O)P-(CH 2)nSi(OEt)3) in acidic media without any structure-directing agent. The hydrolysis of -CN and -P(O)(OEt)2 groups into -COOH and -P(O)(OH)2 involves the in situ formation of dimers by strong hydrogen bonds, which is the crucial step to obtain a solid. The involvement of hydrophobic interactions between alkylene chains was also evidenced. All materials were characterised by X-ray diffraction measurements, elemental analyses and solid-state 13C and 29Si NMR spectroscopies. The accessibility and adsorption capacity of these groups towards lanthanide ions were investigated.

Production and use of derivatized homoserine lactones

The present invention provides analogues of autoinducer molecules that are derivatized to allow their attachment to other molecules and surfaces. Libraries of the autoinducer analogues are also contemplated. Also provided are methods for using the compounds of the invention to produce compositions, such as immunoconjugates, antibodies and vaccines, which are useful for treating and preventing disease states in a subject. The compositions of the invention are also useful in various assays, including assessing the autoinducer load in a subject.