112-17-4Relevant articles and documents
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.
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.
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.
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.
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.