82456-37-9

Upstream product

• 100-39-0 benzyl bromide 
• 140-29-4 phenylacetonitrile 
• 762-72-1 allyl-trimethyl-silane 
• 107-18-6 allyl alcohol 
• 536-74-3 phenylacetylene 
• 106-95-6 allyl bromide 
• 103-80-0 phenylacetyl chloride 
• 122-78-1 phenylacetaldehyde 
• 61077-65-4 1-phenylpent-4-en-2-ol 
• 101-48-4 phenylacetaldehyde dimethyl acetal 
• 24850-33-7 allyltributylstanane 
• 70-11-1 α-bromoacetophenone 
• 7393-43-3 tetraallyl tin 

Downstream Products

• 98746-87-3 (E)-1-phenyl-3-penten-2-one 
• 1329694-59-8 rac-2-benzyl-1-cyclohexylamino-2-methacryloxy-1-oxopent-4-ene 
• 1329694-57-6 rac-2-acryloxy-2-benzyl-1-cyclohexylamino-1-oxopent-4-ene 
• 1329694-53-2 rac-2-benzyl-1-benzylamino-2-methacryloxy-1-oxopent-4-ene 
• 1329694-55-4 rac-2-benzyl-2-methacryloxy-1-(2-methoxy-2-oxoethylamino)-1-oxopent-4-ene 
• 1329694-49-6 rac-2-acryloxy-2-benzyl-1-benzylamino-1-oxopent-4-ene 
• 1329694-81-6 rac-N,2-dibenzyl-6-oxo-3,6-dihydro-2H-pyran-2-carboxamide 
• 1329694-82-7 rac-methyl 2-(2-benzyl-6-oxo-3,6-dihydro-2H-pyran-2-carboxamido)acetate 
• 1329694-84-9 rac-N,2-dibenzyl-5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-carboxamide 
• 1329694-86-1 rac-methyl 2-(2-benzyl-5-methyl-6-oxo-3,6-dihydro-2H-pyran-2-carboxamido)acetate 
• 128913-50-8 (Z)-1-phenylpent-3-en-2-one 
• 1623809-20-0 C₁₈H₁₉BrN₂O₂S 
• 1623809-07-3 C₁₈H₂₀N₂O₂S 
• 1590340-33-2 4-(1H-indol-3-yl)-1-phenylpentan-2-one 

Relevant academic research and scientific papers

Visible Light-Promoted Recyclable Carbon Nitride-Catalyzed Dioxygenation of β,γ-Unsaturated Oximes

A visible-light-induced dioxygenation of β,γ-unsaturated oximes for the synthesis of diverse useful isoxazolines bearing a hydroxyl moiety was developed by employing graphitic carbon nitride (g-C3N4) as a heterogeneous photocatalyst under an air atmosphere. Noted that, the eminent advantages of this metal-free protocol include step economy, easy operation, a recyclable photocatalyst, external reductant-/oxidant-free and mild reaction conditions. Additionally, mechanistic studies indicated hydroxyl radical was generated under the photocatalysis of g-C3N4.

Ni-Catalyzed 1,2-Diarylation of Alkenyl Ketones: A Comparative Study of Carbonyl-Directed Reaction Systems

A nickel-catalyzed 1,2-diarylation of alkenyl ketones with aryl iodides and arylboronic esters is reported. Ketones with a variety of substituents serve as effective directing groups, offering high levels of regiocontrol. A representative product is diversified into a wide range of useful products that are not readily accessible via existing 1,2-diarylation reactions. Preliminary mechanistic studies shed light on the binding mode of the substrate, and Hammett analysis reveals the effect of electronic factors on initial rates.

Development of a Practical, Biocatalytic Synthesis of tert-Butyl (R)-3-Hydroxyl-5-hexenoate: A Key Intermediate to the Statin Side Chain

The HMG-CoA reductase inhibitors, statins, are one of the most effective and bestselling cholesterol-lowering drugs. The use of statins has greatly extended people's lives and improved the quality of their life. Development of a more efficient, stereoselective, and sustainable synthesis of statins is continuingly of utmost importance. In the present study, through screening of ketoreductases (KREDs) and reaction optimization, we have successfully performed a highly stereoselective reduction of ketoester 1a catalyzed by KRED-06 at a pilot-plant scale without the addition of exogenous NADP+, generating 3.21 kg of enantiomerically pure tert-butyl (R)-3-hydroxyl-5-hexenoate ((R)-2a) (96.2% yield, >99.9% enantiomeric excess (ee)). This newly developed biocatalytic process alleviates the cryogenic conditions (-40 °C) employed in our first-generation synthesis of (R)-2a using NaBH4 and (l)-tartaric acid. Coupled with our previously established synthesis of bromocarbonate 3a via a one-pot diastereoselective carboxylation/bromocyclization of (R)-2a, we have developed an innovative, practical synthesis route to statin side chain, possessing great potential to be implemented into industrial production of statins.

Dienamine-Mediated Asymmetric Inverse-Electron-Demand Hetero-Diels–Alder Reaction of Linear Deconjugated Enones: Diversity-Oriented Synthesis of 3,4-Dihydropyrans

The first organocatalytic asymmetric inverse-electron-demand Diels–Alder reaction of deconjugated enones by using a linear dienamine was explored. Electron-poor oxadienes having a cyano group were found to be suitable in this reaction. With a 20 mol-% loa

Exploring the Sponge Consortium Plakortis symbiotica-Xestospongia deweerdtae as a Potential Source of Antimicrobial Compounds and Probing the Pharmacophore for Antituberculosis Activity of Smenothiazole A by Diverted Total Synthesis

Fractionation of the bioactive CHCl3-MeOH (1:1) extracts obtained from two collections of the sponge consortium Plakortis symbiotica-Xestospongia deweerdtae from Puerto Rico provided two new plakinidone analogues, designated as plakinidone B (2) and plakinidone C (3), as well as the known plakinidone (1), plakortolide F (4), and smenothiazole A (5). The structures of 1-5 were characterized on the basis of 1D and 2D NMR spectroscopic, IR, UV, and HRMS analysis. The absolute configurations of plakinidones 2 and 3 were established through chemical correlation methods, VCD/ECD experiments, and spectroscopic data comparisons. When assayed in vitro against Mycobacterium tuberculosis H37Rv, none of the plakinidones 1-3 displayed significant activity, whereas smenothiazole A (5) was the most active compound, exhibiting an MIC value of 4.1 μg/mL. Synthesis and subsequent biological screening of 8, a dechlorinated version of smenothiazole A, revealed that the chlorine atom in 5 is indispensable for anti-TB activity.

Oxime-mediated oxychlorination and oxybromination of unactivated olefins

An oxime-mediated oxychlorination and oxybromination of unactivated olefins relying on palladium catalysis has been developed. A wide range of chlorinated and brominated isoxazolines has been synthesized in moderate to good yields. To demonstrate the value of the method, the brominated isoxazoline has been further converted to other useful synthetic feedstock.

Oxime-mediated facile access to 5-methylisoxazoles and applications in the synthesis of valdecoxib and oxacillin

A palladium-catalyzed efficient synthesis of 5-methylisoxazoles via oxime-mediated functionalization of unactivated olefins is described. The reaction affords a variety of 5-methylisoxazoles in moderate to good yields. To further demonstrate the utility of the method, the rapid synthesis of valdecoxib and oxacillin is reported. (Chemical Equation Presented).

Synthesis of Z-alkenes from Rh(I)-catalyzed olefin isomerization of β,γ-unsaturated ketones

Developing olefin isomerization reactions to reach kinetically controlled Z-alkenes is challenging because formation of trans-alkenes is thermodynamically favored under the traditional catalytic conditions using acids, bases, or transition metals as the catalysts. A new synthesis of Z-alkenes from Rh(I)-catalyzed olefin isomerization of β,γ-unsaturated ketones to α,β-unsaturated ketones was developed, providing an easy and efficient way to access various Z-enones.

First synthesis of α,β-unsaturated lactones with high diversity through the Passerini reaction and ring-closing metathesis (RCM)

A new class of α,β-unsaturated pyran-2-carboxamides was easily accessed by a multicomponent reaction (MCR), followed by a ring-closing metathesis (RCM) using a ruthenium catalyst. In the first step, α-acyloxy carboxamides with two terminal double bonds were formed from terminal unsaturated carboxylic acids, allyl ketones, and isocyanides (Passerini reaction, P-3CR). A new class of α,β-unsaturated pyran-2-carboxamides was easily accessed by amulticomponent reaction (MCR), followedby a ring-closing metathesis (RCM) using a ruthenium catalyst.

Alkoxydienylstannanes via metalation of α,β-unsaturated and α-phenyl acetals: Preparation and synthetic uses in the Stille cross-coupling reaction

Alkoxydienylstannanes via metalation of α,β-unsaturated and α-phenyl acetals were analyzed. Treatment of α,β-unsaturated and α-phenyl acetals with an equimolar mixture of butyllithium and potassium tert-butoxide gave α-metalated 1,3 dienes and vinyl ethers that readily react with chlorotributyltin affording (Z)-functionalized alkoxyvinylstannanes. Stille cross-coupling reaction between these reactants and allyl bromide, iodobenzene, or benzoyl chloride produced derivatives that can be converted into carbonyl compounds according to an umpolung approach.