7011-82-7

Upstream product

• 70038-65-2 3-Oenanthoyl-acrylsaeure-methylester 
• 592-41-6 1-hexene 
• 1490-25-1 succinic acid monomethylester chloride 
• 67-56-1 methanol 
• 4144-54-1 4-oxodecanoic acid 
• 64988-83-6 1,2-dichloro-dec-2-en-4-one 
• 84477-16-7 methyl (+/-)-(2E)-4-hydroxydec-2-enoate 
• 81057-07-0 4,4-Dimethoxy-decanoic acid methyl ester 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 111-25-1 1-bromo-hexane 
• 3395-91-3 Methyl 3-bromopropionate 
• 292638-85-8 acrylic acid methyl ester 
• 70553-34-3 diethyl 2-pentyl-3-oxoglutarate 
• 111-66-0 oct-1-ene 

Downstream Products

• 706-14-9 5-hexyldihydro-2(3H)-furanone 
• 107797-26-2 (R)-5-Hexyl-dihydro-furan-2-one 
• 107797-27-3 (-)-(S)-γ-Decalactone 
• 63095-33-0 γ-(Z)-dec-7-enlactone 
• 1128-08-1 dihydro-cis-jasmone 

Relevant academic research and scientific papers

Chelation-controlled intermolecular alkene and alkyne hydroacylation: The utility of β-thioacetal aldehydes

(Chemical Equation Presented) β-Thioacetal-substituted aldehydes, which are conveniently prepared from the corresponding ynals, can be combined with a range of alkynes or electron-poor alkenes to deliver intermolecular hydroacylation adducts. The reactions employ [Rh(dppe)]ClO4 as a catalyst and are proposed to proceed via a chelated rhodium acyl intermediate. The thioacetal-containing products can be deprotected to the corresponding ketones or reduced to alkanes in good yields.

Photoredox-Catalyzed Isomerization of Highly Substituted Allylic Alcohols by C?H Bond Activation

Photoredox-catalyzed isomerization of γ-carbonyl-substituted allylic alcohols to their corresponding carbonyl compounds was achieved for the first time by C?H bond activation. This catalytic redox-neutral process resulted in the synthesis of 1,4-dicarbonyl compounds. Notably, allylic alcohols bearing tetrasubstituted olefins can also be transformed into their corresponding carbonyl compounds. Density functional theory calculations show that the carbonyl group at the γ-position of allylic alcohols are beneficial to the formation of their corresponding allylic alcohol radicals with high vertical electron affinity, which contributes to the completion of the photoredox catalytic cycle.

An expeditious entry to rare tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidin-7(8H)-ones: A single-step gateway synthesis of glochidine congeners

A single-step gateway synthesis of glochidine and its congeners that possess the rare uncommon tetrahydroimidazo[1,5-c]pyrrolo[1,2-a]pyrimidine core was developed employing histamine and readily available γ-ketoesters. Key features of the developed reaction involve tandem three C–N bonds formation and concomitant annulation of two rings in one pot to access this unique and complex tricyclic structure. Exploration of the unknown bioactivity of these compounds revealed that they elicit antiproliferative activity comparable to the anticancer drug imatinib against 6 cancer cell lines.

Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters to synthesize γ-ketone esters

This work concerns the Mg(OMe)2 promoted allylic isomerization of γ-hydroxy-α,β-alkenoic esters with TMEDA as an additive. The isomerization proceeded under mild conditions and afforded γ-keto esters in high yield (up to 96%) within 2 h. Both (Z)- and (E)-γ-hydroxy-α,β-alkenoic esters were tolerated under the reaction conditions. This transformation involves the in situ formation of a dienolate intermediate from the easily accessible γ-hydroxy-α,β-alkenoic ester. The in situ generated dienolate can react with benzaldehyde and undergo a practical, useful tandem allylic isomerization-Aldol reaction to afford more functionalized compounds.

A synthetic method of chiral gamma-decalactone

A synthetic method of chiral gamma-decalactone is provided. The method includes steps of (1) adding concentrated sulfuric acid into an organic solvent, then adding a catalyst, a ligand and a phase-transfer catalyst into the mixture, finally adding methyl 4-carbonyldecanoate into the mixture, and reacting the mixture; (2) transferring a reaction product obtained in the step (1) into an autoclave, and filling the autoclave with hydrogen to pressurize the autoclave to 3-6 MPa, with the reaction temperature being 60-120 DEG C and reaction time being 4-8 h; and (3) subjecting a reaction product obtained in the step (2) to neutralization, filtration, solvent recovery and distillation to obtain the chiral gamma-decalactone. The reaction temperature and pressure of the method are proper, and production operation is easy so that the method can be used for industrial production. The ee value of the product can be 95% or above.

Solar light-driven photocatalyzed alkylations. Chemistry on the window ledge

Tetrabutylammonium decatungstate photocatalysis is effective for the C-H activation of alkanes, aldehydes, ethers and amides and the alkylation of alkenes occurs effectively by merely exposing the solution to the sun in a glass vessel on a window ledge (u

PROCESS FOR PRODUCTION OF SUBSTITUTED CYCLOPENTANONE

A substituted cyclopentanone represented by the formula (2) can be produced by hydrogenating the double bond in a compound represented by the formula (1) in the presence of a transition metal catalyst by using a carboxylic acid or a specific concentration of a carboxylic acid ester as a solvent. This process can produce a substituted cyclopentanone which is useful as an jasmine-flavored fragrance, an intermediate in the production of the fragrance or the like, in a simple and inexpensive manner at a high cis-form ratio; (1) wherein R1 and R2 represent a substituent having 1 to 8 carbon atoms; and (2) wherein R3 and R4 represent a substituent having 1 to 8 carbon atoms, may be the same as R1 and R2, and may be the same as each other.

Acylation of electrophilic olefins through decatungstate-photocatalyzed activation of aldehydes

(Chemical Equation Presented) With tungsten and lamp: Ketones were prepared by the photocatalytic generation of acyl radicals from aldehydes and trapping them with equimolar amounts of electrophilic alkenes. Photocatalysis with tetrabutylammonium decatungstate is effective also at low temperatures (-20 to -50°C), thus minimizing radical decarbonylation and allowing acylation by highly substituted aldehydes. EWG = electron-withdrawing group.

Rhodium-catalyzed intermolecular chelation controlled alkene and alkyne hydroacylation: Synthetic scope of β-S-substituted aldehyde substrates

The use of β-S-substituted aldehydes in rhodium-catalyzed intermolecular hydroacylation reactions is reported. Aldehydes substituted with either sulfide or thioacetal groups undergo efficient hydroacylation with a variety of electron-poor alkenes, such as enoates, in Stetter-like processes and with both electron-poor and neutral alkynes. In general, the reactions with electron-poor alkenes demonstrate good selectivity for the linear regioisomer, and the reactions with alkynes provide enone products with excellent selectivity for the E-isomers. The scope of the process was shown to be broad, tolerating a variety of substitution patterns and functional groups on both reaction components. A novel CN-directing effect was shown to be responsible for reversing the regioselectivity in a number of alkyne hydroacylation reactions. Catalyst loadings as low as 0.1 mol % were achievable.

1,2,4-Trioxepanes: Redox-cleavable protection for carbonyl groups

(Chemical Equation Presented) 1,2,4-trioxepanes, readily prepared and easily handled derivatives of aldehydes and ketones, are stable to a variety of synthetic conditions and yet easily deblocked with Zn/HOAc or Mg/MeOH to regenerate the parent carbonyl. Trioxepanes may provide an alternative to 1,3-dithianes for acid-stable protection of carbonyl groups.