112-17-4Relevant academic research and scientific papers
Synthesis of 1,10-decanediol diacetate and 1-decanol acetate from furfural
Deng, Chen-Qiang,Jiang, Qin-Zhu,Deng, Jin,Fu, Yao
, p. 2169 - 2176 (2021)
A green and efficient method was developed for upgrading furfural to 1,10-decanediol diacetate and 1-decanol acetate. 92% yield of the acetates was obtained through the tandem benzoin condensation and hydrodeoxygenation reaction. During the benzoin condensation, furfural was catalyzed into furoin in a quantitative yield by the immobilized NHC catalyst under solvent-free conditions. After dissolving the furoin intermediate in acetic acid, the Sc(OTf)3and Pd/C catalytic system was introduced for hydrodeoxygenation. The effects of reaction factors have been investigated in detail and the hydrodeoxygenation process has been explored by1H-NMR and GC-MS.
Hydrophobicity-enhanced magnetic solid sulfonic acid: A simple approach to improve the mass transfer of reaction partners on the surface of the heterogeneous catalyst in water-generating reactions
Mobaraki, Akbar,Movassagh, Barahman,Karimi, Babak
, p. 123 - 133 (2014)
Two novel and environmentally benign organosulfonic acid-functionalized silica-coated magnetic nanoparticle catalysts 1 (Fe3O 4@SiO2@Et-PhSO3H) and 2 (Fe3O 4@SiO2@Me&Et-PhSO3H) were prepared and their surface hydrophobicity was assessed by esterification reaction of fatty alcohols. Also, their water-toleration in two water-generating reactions was investigated, namely: synthesis of bis(indolyl)methane and the Biginelli reaction of benzaldehyde, methyl acetoacetate, and urea under solvent-free conditions. In these reactions, the catalyst 2 that was more hydrophobic and water-resistant showed higher catalytic activity and was characterized extensively by various techniques. This catalyst was successfully used in the Biginelli reaction of a series of aldehydes, β-keto esters, and urea/thiourea for the synthesis of a diverse range of pharmacologically active 3,4-dihydropyrimidin-2-one/thione (DHPM) derivatives. The catalyst 2 was easily separated by an external magnet and the recovered catalyst was reused in five cycles without any significant loss of activity.
ALKENE OXIDATION BY AN IRON(II)/PERSULFATE/ACETIC ACID SYSTEM
Fristad, William E.,Peterson, John R.
, p. 1469 - 1476 (1984)
Mono- and disubstituted alkenes were converted to trans-vicinal diacetates by heating with an iron(II)/persulfate/acetic acid system.The synthetic utility and limitations were identified.A mechanism for the transformation is proposed wich involves an initial addition of sulfate radical anion to the alkene followed by solvolysis, addition, hydrolysis, and acetylation.
Stabilization of long-chain intermediates in solution. Tridecyl radicals and cations
Teodorovi?, Aleksandar V.,Badjuk, Dalibor M.,Stevanovi?, Nenad,Pavlovi?, Radoslav Z.
, p. 357 - 363 (2015)
Tetradecanoic acid was decarboxylated by means of lead(IV) acetate (LTA) under thermal (81 °C) and photolytic (r.t.) conditions in benzene solution. The mixture of products, obtained in thermal reaction, consists of esters (acetoxyalkanes and carboxylates
Structure-Activity relationship of aliphatic compounds for nematicidal activity against pine wood nematode (Bursaphelenchus xylophilus)
Seo, Seon-M.I.,Junheon, Kim,Eunae, Kim,Park, Hye-M.I.,Kim, Young-Joon,Park, I.L.-Kwon
, p. 1823 - 1827 (2010)
Nematicidal activity of aliphatic compounds was tested to determine a structure-activity relationship. There was a significant difference in nematicidal activity among functional groups. In a test with alkanols and 2E-alkenols, compounds with C8-C11 chain length showed 100% nematicidal activity against pine wood nematode, Bursaphelenchus xylophilus, at 0.5 mg/mL concentration. C6-C10 2E-alkenals exhibited >95% nematicidal activity, but the other compounds with C 11-C14 chain length showed weak activity. Nematicidal activity of alkyl acetates with C7-C11 chain length was strong. Compounds belonging to hydrocarbons, alkanals, and alkanoic acetates showed weak activity at 0.5 mg/mL concentration. Nematicidal activity of active compounds was determined at lower concentrations. At 0.25 mg/mL concentration, whole compounds except C8 alkanol, C8 2E-alkenol, and C7 alkanoic acid showed >80% nematicidal activity. C 9-C11 alkanols, C10-C11 2E-alkenols, C8-C9 2E-alkenals, and C9-C10 alkanoic acids showed >80% nematicidal activity at 0.125 mg/mL concentration. Only C11 alkanol exhibited strong nematicidal activity at 0.0625 mg/mL concentration, the lowest concentration that was tested. 2010 American Chemical Society.
ZWITTERIONIC CATALYSTS FOR (TRANS)ESTERIFICATION: APPLICATION IN FLUOROINDOLE-DERIVATIVES AND BIODIESEL SYNTHESIS
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Paragraph 0013; 0028, (2021/01/29)
An amide/iminium zwitterion catalyst has a catalyst pocket size that promotes transesterification and dehydrative esterification. The amide/iminium zwitterions are easily prepared by reacting aziridines with aminopyridines. The reaction can be applied a wide variety of esterification processes including the large-scale synthesis of biodiesel. The amide/iminium zwitterions allow the avoidance of strongly basic or acidic condition and avoidance of metal contamination in the products. Reactions are carried out at ambient or only modestly elevated temperatures. The amide/iminium zwitterion catalyst is easily recycled and reactions proceed in high to quantitative yields.
Genome Mining of Oxidation Modules in trans-Acyltransferase Polyketide Synthases Reveals a Culturable Source for Lobatamides
Ueoka, Reiko,Meoded, Roy A.,Gran-Scheuch, Alejandro,Bhushan, Agneya,Fraaije, Marco W.,Piel, J?rn
supporting information, p. 7761 - 7765 (2020/03/25)
Bacterial trans-acyltransferase polyketide synthases (trans-AT PKSs) are multimodular megaenzymes that biosynthesize many bioactive natural products. They contain a remarkable range of domains and module types that introduce different substituents into growing polyketide chains. As one such modification, we recently reported Baeyer–Villiger-type oxygen insertion into nascent polyketide backbones, thereby generating malonyl thioester intermediates. In this work, genome mining focusing on architecturally diverse oxidation modules in trans-AT PKSs led us to the culturable plant symbiont Gynuella sunshinyii, which harbors two distinct modules in one orphan PKS. The PKS product was revealed to be lobatamide A, a potent cytotoxin previously only known from a marine tunicate. Biochemical studies show that one module generates glycolyl thioester intermediates, while the other is proposed to be involved in oxime formation. The data suggest varied roles of oxygenation modules in the biosynthesis of polyketide scaffolds and support the importance of trans-AT PKSs in the specialized metabolism of symbiotic bacteria.
Method for preparing sebacic acid ester and derivatives thereof (by machine translation)
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Paragraph 0064-0072; 0095; 0098-0135, (2020/05/01)
. Uses the compound of the formula, as the raw material, in the acid solvent selective hydrodeoxygenation to obtain.decanediol and n-decanol: and the method (I) is characterized in that the product is cheap and easily available, product in yield, high in purity, and suitable for industrial production 1,10 - in a simple, process route . The product obtained by the method has the advantages of high yield, high yield and low pollution, to the environment, and the corresponding alcohol, is obtained by saponification reaction. (by machine translation)
IrIII-Catalyzed direct syntheses of amides and esters using nitriles as acid equivalents: A photochemical pathway
Talukdar, Ranadeep
supporting information, p. 5303 - 5308 (2020/04/17)
An unprecedented IrIII[df(CF3)ppy]2(dtbbpy)PF6-catalyzed simple photochemical process for direct addition of amines and alcohols to the relatively less reactive nitrile triple bond is described herein. Various amides and esters are synthesized as the reaction products, with nitriles being the acid equivalents. A mini-library of different types of amides and esters is made using this mild and efficient process, which uses only 1 mol% of photocatalyst under visible light irradiation (λ = 445 nm). The reaction strategy is also efficient for gram-scale synthesis.
Manganese-mediated acetylation of alcohols, phenols, thiols, and amines utilizing acetic anhydride
Jain, Isha,Sharma, Ramandeep,Malik, Payal
supporting information, p. 2952 - 2960 (2019/09/13)
Manganese(II) chloride-catalyzed acetylation of alcohols, phenols thiols and amines with acetic anhydride is reported. This method is environment-friendly and economically viable as it involves inexpensive, relatively benign catalyst, mild reaction condition, and simple workup. Acetylation is performed under the solvent-free condition at ambient temperature and acetylated products obtained in good to excellent yields. Primary, secondary heterocyclic amines, and phenols with various functional groups are smoothly acetylated in good yields. This method exhibits exquisite chemoselectivity, the amino group is preferentially acetylated in the presence of a hydroxyl/thiol group.
