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123-62-6Relevant articles and documents
Diastereoselective synthesis of a lilac aldehyde isomer and its electrophysiological detection by a moth
Schneider, Marc-Andre,Doetterl, Stefan,Seifert, Karlheinz
, p. 1252 - 1259 (2013)
The monoterpene lilac aldehyde (=2-(5-ethenyl-5-methyloxolan-2-yl)propanal) is a widespread flower scent. Lilac aldehyde is emitted in high amounts from nocturnal plant species, and it is highly attractive to nocturnal moth pollinators, such as Hadena bicruris, the pollinating seed predator of Silene latifolia. Lilac aldehyde possesses three stereogenic centers and can occur in eight stereoisomers which induce different antennal responses in H. bicruris. The distribution pattern of stereoisomers differs among plant species, and if H. bicruris has different receptors for detecting different isomers, it may use these differences to discriminate flowers of S. latifolia hosts from flowers of non-host plants. To investigate the question whether the moths have in their antennae one olfactory receptor or several different receptors for the detection of the single lilac aldehyde isomers, (2S,2′S,5′S)-lilac aldehyde was diastereoselectively synthesized. (2S,2′S,5′S)-Lilac aldehyde and its isomeric mixture were tested electrophysiologically on antennae of H. bicruris. The results displayed antennal responses, which are characteristic for a single receptor that detects the different lilac aldehyde isomers. Copyright
A facile method for Rh-catalyzed decarbonylativeortho-C-H alkylation of (hetero)arenes with alkyl carboxylic acids
Tian, Yiqiang,Liu, Xiaojie,He, Bangyue,Ren, Yuxi,Su, Weiping
, p. 19827 - 19831 (2021)
A facile and effective method for Rh-catalyzed directortho-alkylation of C-H bonds in (hetero)arenes with commercially available carboxylic acids has been developed. This strategy was initiated byin situconversion of carboxylic acids to anhydrides which, without isolation, underwent Rh-catalyzed direct decarbonylative cross-coupling of aryl carboxamides containing 8-aminoquinoline. The reaction proceeds with high regioselectivity and exhibits a broad substrate scope as well as functional group tolerance.
Generation of basic centers in high-silica zeolites and their application in gas-phase upgrading of bio-oil
Keller, Tobias C.,Rodrigues, Elodie G.,Perez-Ramirez, Javier
, p. 1729 - 1738 (2014)
High-silica zeolites have been reported recently as efficient catalysts for liquid- and gas-phase condensation reactions because of the presence of a complementary source of basicity compared to Al-rich basic zeolites. Herein, we describe the controlled generation of these active sites on silica-rich FAU, BEA, and MFI zeolites. Through the application of a mild base treatment in aqueous Na2CO3, alkali-metal-coordinating defects are generated within the zeolite whereas the porous properties are fully preserved. The resulting catalysts were applied in the gas-phase condensation of propanal at 673 K as a model reaction for the catalytic upgrading of pyrolysis oil, for which an up to 20-fold increased activity compared to the unmodified zeolites was attained. The moderate basicity of these new sites leads to a coke resistance superior to traditional base catalysts such as CsX and MgO, and comparable activity and excellent selectivity is achieved for the condensation pathways. Through strategic acid and base treatments and the use of magic-angle spinning NMR spectroscopy, the nature of the active sites was investigated, which supports the theory of siloxy sites as basic centers. This contribution represents a key step in the understanding and design of high-silica base catalysts for the intermediate deoxygenation of crude bio-oil prior to the hydrotreating step for the production of second-generation biofuels. Creating new basic sites: Through activation treatments in alkaline media, basic sites with high activity, stability, and selectivity are generated in high-silica FAU, BEA, and MFI zeolites, which enable the efficient deoxygenation of pyrolysis oil by condensation reactions. Intermediate bio-oil upgrading is key for the sustainable and profitable production of advanced biofuels.
Isothiourea-Catalyzed Atroposelective N-Acylation of Sulfonamides
Ong, Jun-Yang,Ng, Xiao Qian,Lu, Shenci,Zhao, Yu
supporting information, p. 6447 - 6451 (2020/09/02)
We report herein an atroposelective N-acylation of sulfonamides using a commercially available isothiourea catalyst, (S)-HBTM, with a simple procedure. The N-sulfonyl anilide products can be obtained in good to high enantiopurity, which represents a new axially chiral scaffold. The application of the product as a chiral iodine catalyst is also demonstrated for the asymmetric α-oxytosylation of propiophenone.
Anhydrides from aldehydes or alcohols via oxidative cross-coupling
Gaspa, Silvia,Amura, Ida,Porcheddu, Andrea,De Luca, Lidia
supporting information, p. 931 - 939 (2017/02/10)
A novel type of metal-free oxidative cross-coupling for the synthesis of symmetrical and mixed anhydrides from aldehydes or benzylic alcohols has been developed. The aldehydes or alcohols were converted in situ into their corresponding acyl chlorides, which were then reacted with an array of carboxylic acids. The methodology has a general applicability, and was successfully employed to prepare either aromatic or aliphatic symmetrical anhydrides and mixed anhydrides, which are very unstable compounds.