2825-92-5

Usage

InChI:InChI=1/C10H18O2/c1-2-3-4-5-6-9-7-8-10(11)12-9/h9H,2-8H2,1H3

Upstream product

• 4144-54-1 4-oxodecanoic acid 
• 111-71-7 heptanal 
• 58779-08-1 1-(Diethoxyphosphoryl)-N,N-dimethyl-1-propen-1-amin 
• 55915-64-5 (Z)-2-Dimethylamino-but-2-enenitrile 
• 19464-44-9 methyl 3-(tri-n-butylstannyl)propionate 
• 37810-94-9 decane-1,4-diol 
• 7011-82-7 methyl 4-oxodecanoate 
• 158197-40-1 undec-1-ene-5-ol 
• 623-71-2 ethyl 3-chloropropanoate 
• 111-66-0 oct-1-ene 
• 64-19-7 acetic acid 
• 79-08-3 bromoacetic acid 
• 105-53-3 diethyl malonate 
• 2984-50-1 1,2-Epoxyoctane 

Downstream Products

• 77461-95-1 4-Phenylselanyl-decanoic acid 
• 17369-51-6 4-hydroxydecanoic acid 
• 2602-61-1 N,N-diethyldecanamide 
• 107797-26-2 (R)-5-Hexyl-dihydro-furan-2-one 
• 107797-27-3 (-)-(S)-γ-Decalactone 
• 37810-94-9 decane-1,4-diol 
• 112-37-8 undecylenic acid 
• 43160-78-7 4-oxodecanal 
• 3208-32-0 2-hexyltetrahydrofuran 

Relevant academic research and scientific papers

Lewis acid-catalysed isomerisation of thionolactones to thiolactones: inversion of configuration

Boron trifluoride and indium(III) trifluoromethanesulfonate were found to efficiently catalyse the isomerisation of thionolactones to thiolactones in good yields. When applied to an optically active γ-thionolactone, the isomerisation reaction proceeded with a complete inversion of configuration by using BF3·Et2O.

Hydroacylation of Alkyl Vinyl Ketones and Acrylic Esters Using Organotetracarbonylferrates. Synthesis of 1,4-Dicarbonyl Compounds

Alkyl vinyl ketones and acrylic esters were hydroacylated with organotetracarbonylferrates to the corresponding 1,4-diketones and 4-oxo carboxylic acid derivatives in good yield in dipolar aprotic solvents such as N,N-dimethylacetamide.Addition of 18-crown-6 improved the yield. cis-Jasmone and γ-jasmolactone were synthesized by use of these reactions.

LACTONIZATION OF γ-HALO ESTERS WITH SILICA GEL CATALYST

A facile synthesis of γ-butyrolactones by the lactonization of percentg-halo esters with silica gel catalyst and its application to the stereoselective synthesis of (+/-)-canadensolide are described

Biotransformation of saturated monohydroxyl fatty acids to 2-tetrahydrofuranyl acetic acid derivatives: Mechanism of formations and the biological activity of 5-n-hexyl-tetrahydrofuran-2-acetic acid

The transformation of 12-hydroxyoctadecanoic acid (12-HOA) to 5-n-hexyl-tetrahydofuran-2-acetic acid (5-HTFA) by Bacillus lentus NRRL B-14864 was carried out in the presence and absence of oligomycin, 2-bromooctanoic acid (2-BA), or sodium azide. Methyl esters of the transformation products were analyzed by gas chromatography and gas chromatography/mass spectroscopy. Results suggest that the production of 5-HTFA from 12-HOA by B-14864 was through the fatty acid beta-oxidation pathway. Three-day old driedfruit beetle pupae were topically treated with 5-HTFA to test for juvenile hormone activity, and 5-HTFA was found to possess juvenile hormone-like activity in pure form but not when it was diluted to 10 percent.

Stereoselective synthesis of chiral δ-lactonesviaan engineered carbonyl reductase

A carbonyl reductase variant,SmCRM5, fromSerratia marcescenswas obtained through structure-guided directed evolution. The variant showed improved specific activity (U mg?1) towards most of the 16 tested substrates and gave high stereoselectivities of up to 99% in the asymmetric synthesis of 13 γ-/δ-lactones. In particular, SmCRM5showed a 13.8-fold higher specific activity towards the model substrate,i.e., 5-oxodecanoic acid, and gave (R)-δ-decalactone in 99% ee with a space-time yield (STY) of 301 g L?1d?1. The preparative synthesis of six δ-lactones in high yields and with high enantiopurities showed the feasibility of the biocatalytic synthesis of these high-value-added chemicals, providing a cost-effective and green alternative to noble-metal catalysis.

Photo-induced radical borylation of hemiacetals via C–C bond cleavage

In this study, we reported a photo-induced radical borylation of hemiacetal derivatives via C–C bond cleavage. This transformation can be realized under mild conditions with simple reaction settings and irradiation of visible light. A series of substrates, including both cyclic and linear hemiacetal derivatives, were effectively transformed to the borylation product in moderate to good yields. Finally, the mechanism was studied in detail by DFT calculations, suggesting insight of the radical borylation process.

MODIFIED AMINE LIPIDS

The disclosure provides ionizable amine lipids and salts thereof (e.g., pharmaceutically acceptable salts thereof) useful for the delivery of biologically active agents, for example delivering biologically active agents to cells to prepare engineered cells. The ionizable amine lipids disclosed herein are useful as ionizable lipids in the formulation of lipid nanoparticle-based compositions.

Efficient Stereoselective Synthesis of Structurally Diverse γ- and δ-Lactones Using an Engineered Carbonyl Reductase

Structurally diverse γ- and δ-lactones were efficiently synthesized stereoselectively using an engineered carbonyl reductase from Serratia marcescens (SmCRV4). SmCRV4 exhibited improved activity (up to 500-fold) and thermostability toward 14 γ-/δ-keto acids and esters, compared with the wild-type enzyme, with 110-fold enhancement in catalytic efficiency (kcat/Km) toward methyl 4-oxodecanoate. The preparative synthesis of alkyl and aromatic γ- and δ-lactones with 95 %–>99 % ee and 78 %–90 % yields was demonstrated. The highest space-time yield, 1175 g L?1 d?1, was achieved for (R)-γ-decalactone.

Calcium(II)- And Triflimide-Catalyzed Intramolecular Hydroacyloxylation of Unactivated Alkenes in Hexafluoroisopropanol

We report an efficient intramolecular hydroacyloxylation of unactivated alkenes, offering a streamlined access to relevant γ-lactones, which features the utilization of either a calcium(II) salt or triflimide as a catalyst in hexafluoroisopropanol. This method could be applied to the synthesis of natural products and the late-stage functionalization of natural and bioactive molecules. Additionally, DFT computations were used to elucidate the twist of reactivity observed between the hydroamidation and hydroacyloxylation of unactivated alkenes regarding the formation of 5- and 6-membered rings.

W(OTf)6-Catalyzed Synthesis of Γ-Lactones by Ring Contraction of Macrolides or Ring Closing of Terminal Hydroxyfatty Acids in Ionic Liquid

γ-Lactones are an important class of fine chemical products and are widely used in perfumes, medicines, pesticides, dyes, and other fields. Herein, a new method for γ-lactones preparation based on ring contraction was developed. Starting from macrolides, W(OTf)6 was used to catalyze the ring-opening polymerization then depolymerization. The depolymerization step was not a common ring-closing process, and the carbon number of the ring was reduced one by one by rearrangement to form the most thermodynamically stable five-membered ring compounds. γ-Caprolactone (180 °C for 10 h) was obtained in a yield of 94 % when [EMIM]OTf was used as the solvent, and the yield of isolated product was up to 85 %. The interaction of various components and the reaction mechanism were studied by FTIR spectroscopy and 1H NMR spectroscopy, respectively. Furthermore, γ-lactones could be produced when the substrate was extended to terminal hydroxyfatty acids. Unexpectedly, the catalyst was poisoned by 1 equivalent of H2O added during the process and thus the yield decreased greatly. The reaction is green and simple, and proceeds in one pot with high atom economy (100 % for macrolides and with water as the only byproduct for terminal hydroxyfatty acid), which provides a promising approach to synthesizing γ-lactones.