57084-16-9

Upstream product

• 74567-98-9 4-hydroxynonanoic acid 
• 129920-91-8 (E)-(R)-4-Methoxymethoxy-non-2-enoic acid ethyl ester 
• 104-61-0 γ-nonalactone 
• 73642-83-8 4-oxononanenitrile 
• 135106-71-7 C₁₉H₃₂⁽²⁾H₂O₃ 
• 7779-53-5 (R)-4-Hydroxy-nonanoic acid 
• 107736-68-5 ethyl (R)-4-hydroxynonanoate 
• 107736-57-2 (R)-4-Acetoxy-nonanoic acid ethyl ester 
• 52253-57-3 (1R,2S)-N-methylephedrinyl acrylate 
• 66-25-1 hexanal 
• 187600-79-9 (1S,2R)-N-methylephedrinyl acrylate 
• 6064-52-4 4-oxononanoic acid 
• 814-68-6 acryloyl chloride 
• 6789-80-6 (3Z)-hexenal 

Downstream Products

• 22094-44-6 γ-Hydroxypelargonsaeurehydrazid 
• 63357-96-0 (R)-(+)-γ-nonalactone 
• 7779-53-5 (S)-4-Hydroxy-nonanoic acid 
• 74567-98-9 4-hydroxynonanoic acid 
• 63357-97-1 (S)-γ-nonanolide 
• 18402-84-1 (3E)-dec-3-en-2-one 
• 42521-57-3 (5E)-dec-5-en-2-one 
• 24089-15-4 (4E)-dec-4-en-2-one 

Relevant academic research and scientific papers

Application of an ephedrine chiral linker in a solid-phase, 'asymmetric catch-release' approach to γ-butyrolactones

A Sm(II)-mediated, asymmetric, intermolecular ketyl-olefin addition employing α,β-unsaturated esters linked to resin through an ephedrine 'chiral link' has been applied in a direct 'asymmetric catch-release' approach to γ-butyrolactones.

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.

Preparation method of coconut aldehyde

The invention discloses a preparation method of coconut aldehyde. The method comprises the following steps: step 1, mixing n-hexanol, acrylic acid and di-tert-butyl peroxide with uniform stirring, andcarrying out heat insulation on an obtained mixed solution; step 2, mixing n-hexanol with a beta molecular sieve catalyst, performing stirring, heating and heat preservation in a nitrogen environment, dropwise adding the mixed solution obtained in the step 1 at a constant speed during the heat preservation, continuously separating out byproducts including water, tert-butyl alcohol and methanol inthe reaction process, and continuously performing reacting for 1-2 hours after dropwise adding is finished; and step 3, after the reaction is finished, performing cooling, recovering low-boiling-point substances and n-hexanol in the reaction solution in vacuum, performing cooling after the recovery is finished to obtain a crude product, and carrying out reduced pressure distillation on the crudeproduct to obtain a coconut aldehyde product. The novel environment-friendly high-efficiency beta molecular sieve catalyst adopted by the invention shows good catalytic activity and selectivity in coconut aldehyde synthesis, can be repeatedly used, can be cyclically regenerated in manners of high-temperature roasting and the like, and is high in reaction yield, and the technological process is easy to control, and is beneficial to forming industrial large-scale production.

Identification of Bond-Weakening Spirosilane Catalyst for Photoredox α-C?H Alkylation of Alcohols

The development of catalyst-controlled site-selective C(sp3)?H functionalization is a current major challenge in organic synthesis. This paper describes DFT-guided identification of pentavalent silicate species as a novel bond-weakening catalyst for the α-C?H bonds of alcohols together with a photoredox catalyst and a hydrogen atom transfer catalyst. Specifically, Martin's spirosilane accelerated α-C?H alkylation of alcohols. (Figure presented.).

A Bond-Weakening Borinate Catalyst that Improves the Scope of the Photoredox α-C-H Alkylation of Alcohols

The development of catalyst-controlled, site-selective C(sp 3)-H functionalization reactions is currently a major challenge in organic synthesis. In this paper, a novel bond-weakening catalyst that recognizes the hydroxy group of alcohols through formation of a borate is described. An electron-deficient borinic acid-ethanolamine complex enhances the chemical yield of the α-C-H alkylation of alcohols when used in conjunction with a photoredox catalyst and a hydrogen atom transfer catalyst under irradiation with visible light. This ternary hybrid catalyst system can, for example, be applied to functional-group-enriched-peptides.

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.

Preparation method of (R)-(+)-gamma-amylbutyrolactone and (R)-(-)-gamma-amylbutyrolactone

The invention discloses a preparation method of (R)-(+)-gamma-amylbutyrolactone and (R)-(-)-gamma-amylbutyrolactone. The preparation method comprises (1) carrying out ring opening on racemic gamma-amylbutyrolactone by an inorganic alkali solution to obtain an aqueous solution of gamma-hydroxy acid-base metal salt, then adding an organic solvent into the solution, adjusting the mixed solution to weak acidity through an inorganic acid so that the produced gamma-hydroxy acid enters an organic phase, separating the organic phase and carrying out drying, (2) adding (S)-(-)-alpha-phenethylamine or (R)-(+)-alpha-phenethylamine into the obtained organic phase, carrying out crystallization to obtain low optical activity gamma-hydroxy acid phenylethylamine salt, and (3) adding the obtained amine salt into a resolving solvent, carrying out stirring for dissolution, carrying out crystallization and filtration, dissolving the filter cake through water, adding an inorganic acid into the solution, carrying out acidification cyclization, and extracting R)-(+)-gamma-amylbutyrolactone or (S)-(-)-alpha-phenethylamine through an organic solvent. The splitting method is easy to operate and can acquiretwo configurations of chiral gamma-phenethylamine. The products have pure and natural aroma. The preparation method has the advantages of simple processes, mild conditions and high enantiomeric excess.

Production method for synthesizing coconut aldehyde synthetic fragrance through reactive distillation

The invention belongs to the technical field of fine chemical production, and specifically relates to a production method for synthesizing a coconut aldehyde synthetic fragrance through reactive distillation. The production method comprises the following steps: (a) mixing raw materials through a pipeline so as to obtain a batched mixture; (b) releasing hexanol into a preheater from the interior ofa hexanol high-level tank, and carrying out preheating; (c) pumping the hexanol into the high-boiling-point feeding section of the reaction zone of a reactive distillation tower, pumping the batchedmixture into the low-boiling-point feeding section of the reaction zone of the reactive distillation tower through a dropwise adding pump; (d) separating a crude coconut aldehyde product from the tower bottom of the reactive distillation tower; (e) transferring the hexanol separated in the step (d) into the preheater through a material pump, and allowing the hexanol to continue participating in areaction; and (f) further subjecting the separated crude coconut aldehyde product to separation and purification. The production method provided by the invention adopts a reactive distillation technology to separate by-products namely methanol and tert-butanol and low-boiling-point impurities generated by side reactions out of a reaction system in time, greatly shortens the reaction time, and improves the reaction speed and reaction efficiency.

Method for synthesizing coconut aldehyde synthetic spice through reactive distillation

The invention belongs to the technical field of fine chemical engineering, and particularly relates to a method for synthesizing a coconut aldehyde synthetic spice through reactive distillation. The method comprises the following steps: (a) mixing hexyl alcohol, methyl acrylate and di-tert-butyl peroxide to obtain a mixture; (b) weighing hexyl alcohol, adding the hexyl alcohol into a heater of a reactive distillation tower, and putting the proportioned mixture obtained in the step (a) into a reaction area of the reactive distillation tower; (c) introducing condensate water at the tower top ofthe reactive distillation tower, and separating out a coconut aldehyde crude product from the tower bottom; and (d) transferring the coconut aldehyde crude product into a rotary evaporator, controlling the vacuum degree, the temperature and the rotating speed, and carrying out collecting to obtain the coconut aldehyde. According to the invention, a reactive rectification technology is adopted, andby-products are separated out from the reaction system in time, so that dual effects that separation is promoted by a reaction and the reaction is promoted by separation are achieved, the reaction efficiency is improved, and the reaction yield is ensured.

Simple Preparation of Rhodococcus erythropolis DSM 44534 as Biocatalyst to Oxidize Diols into the Optically Active Lactones

In the current study, we present a green toolbox to produce ecological compounds like lactone moiety. Rhodococcus erythropolis DSM 44534 cells have been used to oxidize both decane-1,4-diol (2a) and decane-1,5-diol (3a) into the corresponding γ- (2b) and δ-decalactones (3b) with yield of 80% and enantiomeric excess (ee)?=?75% and ee?=?90%, respectively. Among oxidation of meso diols, (?)-(1S,5R)-cis-3-oxabicyclo[4.3.0]non-7-en-2-one (5a) with 56% yield and ee?=?76% as well as (?)-(2R,3S)-cis-endo-3-oxabicyclo[2.2.1]dec-7-en-2-one (6a) with 100% yield and ee?=?90% were formed. It is worth mentioning that R. erythropolis DSM 44534 grew in a mineral medium containing ethanol as the sole source of energy and carbon Chirality 28:623–627, 2016.