2777-66-4

Usage

Uses

Used in Chemical Synthesis:
METHYL 10-UNDECYNOATE is used as a chemical reagent for the synthesis of α-substituted vinylsilanes through hydrosilylation reactions. This application is facilitated by the use of ruthenium cationic acetonitrile cyclopentadienyl half-sandwich complexes as catalysts. The resulting α-substituted vinylsilanes have potential applications in various fields, including materials science, pharmaceuticals, and electronics.
Used in Material Science:
In the field of material science, METHYL 10-UNDECYNOATE is used as a precursor for the development of novel materials with specific properties. The hydrosilylation reaction involving METHYL 10-UNDECYNOATE allows for the creation of new silane-based materials, which can be tailored for various applications such as coatings, adhesives, and sealants.
Used in Pharmaceutical Industry:
METHYL 10-UNDECYNOATE may also find applications in the pharmaceutical industry, where it can be used as an intermediate in the synthesis of various drug molecules. The unique reactivity of METHYL 10-UNDECYNOATE enables the formation of complex molecular structures with potential therapeutic properties.
Used in Electronics:
In the electronics industry, METHYL 10-UNDECYNOATE can be utilized in the development of advanced materials for semiconductor devices, sensors, and other electronic components. The hydrosilylation reaction involving METHYL 10-UNDECYNOATE can lead to the creation of new materials with improved electrical and optical properties, contributing to the advancement of electronic technology.

InChI:InChI=1/C12H20O2/c1-3-4-5-6-7-8-9-10-11-12(13)14-2/h1H,4-11H2,2H3

Upstream product

• 67-56-1 methanol 
• 2777-65-3 undec-10-ynoic acid 
• 57835-78-6 undeca-10-ynoic acid chloride 
• 111-81-9 Methyl 10-undecenoate 
• 6308-96-9 10,11-dibromo-undecanoic acid 
• 112-38-9 10-undecenoic acid 
• 186581-53-3 diazomethane 
• 18414-58-9 diphenylmethylsilanecarboxylic acid 
• 124-41-4 sodium methylate 
• 75-77-4 chloro-trimethyl-silane 
• 49827-05-6 methyl 10,11-dibromoundecanoate 

Downstream Products

• 24567-41-7 10,12-docosadiyndioic acid dimethyl ester 
• 103644-30-0 1,1-diphenyl-undec-10-yn-1-ol 
• 2774-84-7 undec-10-yn-1-ol 
• 2777-65-3 undec-10-ynoic acid 
• 112-43-6 10-Undecen-1-ol 
• 1028295-36-4 (E)-(2-fluoro-10-methoxycarbonyl-1-decenyl)(4-methylphenyl)iodonium fluoride 
• 506-45-6 22-hydroxydocosanoic acid 
• 556776-84-2 10-(benzyldimethylsilyl)-10-undecenoic acid methyl ester 
• 94030-75-8 ethyl ester of dodec-11-ynoic acid 
• 765-17-3 (10E,12Z)-hexadeca-10,12-dien-1-ol 
• 51953-88-9 1-[(tetrahydropyran-2-yl)oxy]undec-10-yne 
• 64437-48-5 Δ10-hexadecenol 
• 2511-97-9 (10Z)-hexadec-10-enoic acid 

Relevant academic research and scientific papers

Synthesis of β-Fluorovinyliodonium Salts by the Reaction of Alkynes with Hypervalent Iodine/HF Reagents

The reaction of alkynes with PhIO and Py·HF followed by treatment with BF3·OEt2 gave β-fluorovinyliodonium tetrafluoroborates in good to high yields. More conveniently, the reaction using PhI and Py·HF in the presence of m-CPBA also afforded β-fluorovinyliodonium tetrafluoroborates in good yields. These methods have the advantages that β-fluorovinyliodonium salts can be prepared without ArIF2.

Photoinitiated anti-Hydropentafluorosulfanylation of Terminal Alkynes

A photoinitiated anti-hydropentafluorosulfanylation of terminal alkynes using SF5Cl and (TMS)3SiH as the hydrogen atom donor is reported. This transformation generates selectively (Z)-(1-alken-1-yl)pentafluoro-λ6-sulfanes

Nickel-Mediated Alkoxycarbonylation for Complete Carbon Isotope Replacement

Many commercial drugs, as well as upcoming pharmaceutically active compounds in the pipeline, display aliphatic carboxylic acids or derivatives thereof as key structural entities. Synthetic methods for rapidly accessing isotopologues of such compounds are highly relevant for undertaking critical pharmacological studies. In this paper, we disclose a direct synthetic route allowing for full carbon isotope replacement via a nickel-mediated alkoxycarbonylation. Employing a nickelII pincer complex ([(N2N)Ni-Cl]) in combination with carbon-13 labeled CO, alkyl iodide, sodium methoxide, photocatalyst, and blue LED light, it was possible to generate the corresponding isotopically labeled aliphatic carboxylates in good yields. Furthermore, the developed methodology was applied to the carbon isotope substitution of several pharmaceutically active compounds, whereby complete carbon-13 labeling was successfully accomplished. It was initially proposed that the carboxylation step would proceed via the in situ formation of a nickellacarboxylate, generated by CO insertion into the Ni-alkoxide bond. However, preliminary mechanistic investigations suggest an alternative pathway involving attack of an open shell species generated from the alkyl halide to a metal ligated CO to generate an acyl NiIII species. Subsequent reductive elimination involving the alkoxide eventually leads to carboxylate formation. An excess of the alkoxide was essential for obtaining a high yield of the product. In general, the presented methodology provides a simple and convenient setup for the synthesis and carbon isotope labeling of aliphatic carboxylates, while providing new insights about the reactivity of the N2N nickel pincer complex applied.

IMMUNOTHERAPEUTIC AGENT

Compounds for use in the treatment of sepsis and/or the prevention or treatment of post-sepsis syndrome.

HYDROXY FATTY ACID COMPOUNDS AND USES THEREOF FOR DISEASE TREATMENT AND DIAGNOSIS

A compound of formula (I): wherein R represents a hydroxy substituted C24 - C40 straight chain aliphatic group containing at least one double bond in the carbon chain; and at least one carbon in the chain is substituted with a hydroxy group. Such compounds are useful for detecting inflammation, inflammatory disorders and cancer in a subject, and can also be used in therapeutic applications including treatment and/or prevention of these conditions. Pharmaceutical compositions, combinations and supplements, as well as methods of treatment using the described compounds are therefore also described.

IMMUNOTHERAPEUTIC AGENT

The invention relates to a compound which is an ester of 1, 2, 3-propanetriol with one or more C11 to C24 fatty acids, wherein at least one fatty acid has at least one double bond. The compound is useful in the treatment of chronic inflammatory disorders.

Synthesis of carboxyl-tethered symmetric conjugated polyenes as fluorescent transmembrane probes of lipid bilayers

The synthesis of a new series of fluorescent transmembrane probes in which two hydrophilic methyl ester or carboxyl groups are connected by a polymethylene chain, with four, five or six conjugated double bonds in a central position, is reported. The length of the linear structures was designed to match the width of typical lipid bilayers. These bolaamphiphilic compounds result, with overall yields higher than 80%, from an easy PdII-catalyzed double cross-coupling between terminal acetylene esters and conjugated 1,ω-dihalopolyenes, followed by selective triple bond partial reduction with activated zinc, and iodine isomerization to the all-(E) isomer. An alternative approach, based on a Stille double cross-coupling between the appropriate all-(E)-ω-halopolyenes and (E)-bis(tributylstannyl)ethene, yielded mixtures that could not be resolved by standard chromatographic methods due to the presence of other simultaneous coupling reactions, which are also discussed in detail. Nevertheless, the Stille method can be of utility for the obtention of carbonyl-polyene conjugated analogs. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Ultrasound in fatty acid chemistry: facile dehydrobromination of dibromo fatty esters to acetylenic ester derivatives

Dehydrobromination of dibromo derivatives of olefinic fatty acids was accomplished using KOH in 20percent aqueous ethanol under cocomitant ultrasonic irradiation (20 kHz) for 30 min at ambient temperature to give the corresponding acetylenic fatty acid derivatives (52-72percent yield).Ten different dibromo fatty acid substrates were used.Products include: fatty acids with a terminal or internal acetylenic bond; acetylenic fatty acids containing an additional functional group, such as hydroxy, chloro or azide group.The structures of the products were characterized by infrared and NMR spectroscopy. - Keywords: acetylenic fatty esters; dehydrobromination; dibromo fatty esters; ultrasond

Synthesis of Two New Phospholipidic Fluorescent Probes for Membrane Studies.

Two new fluorenyl-phospholipidic probes have been prepared in good yield by a Pd0/CuI-catalyzed cross-coupling reaction.