591-11-7Relevant articles and documents
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Ogibin et al.
, (1976)
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Synthesis of renewable diesel with 2-methylfuran and angelica lactone derived from carbohydrates
Wang, Wei,Li, Ning,Li, Shanshan,Li, Guangyi,Chen, Fang,Sheng, Xueru,Wang, Aiqin,Wang, Xiaodong,Cong, Yu,Zhang, Tao
, p. 1218 - 1223 (2016)
Diesel and jet fuel range branched alkanes were first synthesized by the combination of hydroxyalkylation/alkylation (HAA) of 2-methylfuran with angelica lactone and subsequent hydrodeoxygenation. Compared with the previous ethyl levulinate route, the angelica lactone route exhibited evident advantages at higher HAA reactivity.
Synthesis of diastereo- and enantiomerically pure anti-3-methyl-1,4- pentanediol via lipase catalysed acylation
Lindstroem, Mona,Hedenstroem, Erik,Bouilly, Sandrine,Velonia, Kelly,Smonou, Ioulia
, p. 1355 - 1360 (2005)
Racemic trans-4,5-dimethylhydrofuran-2(3H)-one was synthesised from 5-methyl-furan-2(3H)-one, (α-angelica lactone). The key reaction in the synthesis was the 1,4-conjugate addition of an organocuprate to 5-methylfuran-2(5H)-one (β-angelica lactone). Different types of organocuprates were tested with the highest anti:syn ratio of 99.4:0.6 being obtained by the use of a Gilman organocuprate reagent. The enantioselective acylation of racemic 3-methyl-pentan-1,4-diol, catalysed by a variety of lipases in organic media, was investigated. The highest enantioselectivity (E >400) was obtained when Novozyme 435 was used as the catalyst at a water activity of aw ～ 0. Thus, both enantiomers, (3S,4R)- and (3R,4S)-3-methyl- pentan-1,4-diol, were obtained in very high diastereomeric (>99% de) and enantiomeric purities (>99.8% and >97.4% ee, respectively).
Biosynthesis of Pseudomonas-Derived Butenolides
Chowdhury, Somak,Klapper, Martin,Menzel, Klaus-Dieter,Paschold, André,Rosenbaum, Miriam A.,Schlabach, Kevin,Stallforth, Pierre,Zhang, Shuaibing
supporting information, p. 5607 - 5610 (2020/02/04)
Butenolides are well-known signaling molecules in Gram-positive bacteria. Here, we describe a novel class of butenolides isolated from a Gram-negative Pseudomonas strain, the styrolides. Structure elucidation was aided by the total synthesis of styrolide A. Transposon mutagenesis enabled us to identify the styrolide biosynthetic gene cluster, and by using a homology search, we discovered the related and previously unknown acaterin biosynthetic gene cluster in another Pseudomonas species. Mutagenesis, heterologous expression, and identification of key shunt and intermediate products were crucial to propose a biosynthetic pathway for both Pseudomonas-derived butenolides. Comparative transcriptomics suggests a link between styrolide formation and the regulatory networks of the bacterium.
Cascade reaction engineering on zirconia-supported mesoporous MFI zeolites with tunable Lewis-Br?nsted acid sites: a case of the one-pot conversion of furfural to γ-valerolactone
Huang, Jun,Kim, Jaeheon,Kim, Jeong-Chul,Kim, Kyung Duk,Ryoo, Ryong,Teoh, Wey Yang
, p. 35318 - 35328 (2020/10/19)
Catalytic cascade reactions are strongly desired as a potential means of combining multistep reactions into a single catalytic reactor. Appropriate catalysts composed of multi-reactive sites to catalyze cascade reactions in a sequential fashion are central to such efforts. Here, we demonstrate a bifunctional zeolite catalyst with close proximity of Br?nsted and Lewis acid sites through the synthesis of a mesoporous ZrO2[Al]MFI nanosponge (NS). The unique mesopores of the MFI-NS allow the confinement of zirconium oxide clusters (Lewis acid sites, LA) within the few-unit-cell-thin MFI aluminosilicate zeolite wall (Br?nsted acid sites, BA). Such a structure is clearly distinct from the conventional MFI zeolite, where the agglomeration of zirconium oxide clusters onto the external surface area within the crystal bulk is not possible, resulting in segregated BA and LA sites on the internal and external zeolite, respectively. By bringing the BA and LA within ZrO2[Al]MFI-NS 30, we uncovered a more efficient catalytic route for the conversion of furfural (100% within 2 h) to γ-valerolactone (GVL) (83%). This route is only evident when the long molecular diffusion path, in the most extreme case of physically mixed ZrO2-(LA) and Al-zeolites (BA) (45% of GVL yield), is eliminated. Unlike the bifunctional ZrO2-Al-beta (GVL yield of 75%), where the BA concentration is greatly compromised at the expense of LA formation, we also show that the ZrO2[Al]MFI-NS is able to maintain a high density and good stability of both types of acids.
