18402-84-1

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 111-71-7 heptanal 
• 881650-04-0 dec-3c-en-2-one 
• 1067-71-6 Diethyl (2-oxopropyl)phosphonate 
• 872-05-9 1-Decene 
• 2236-01-3 acetonyltriphenylphosphonium bromide 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 2384-70-5 dec-2-yne 
• 67-56-1 methanol 
• 67-64-1 acetone 
• 78094-59-4 1,2-decadien-4-ol 
• 2117-11-5 4-pentyn-2-ol 
• 104-61-0 γ-nonalactone 
• 64-19-7 acetic acid 

Downstream Products

• 1620209-14-4 (R,E)-1,1,1-trifluoro-2-hydroxy-2-phenyldodec-5-en-4-one 
• 1280725-07-6 1-cyclohexyl-2-hexyl-1,4-pentanedione 
• 420849-80-5 (2S,3R)-1-(3-hexyl-oxiranyl)-ethanone 
• 1092535-02-8 (5R)-5-hexyl-3-methyl-1,2-dioxolan-3-ol 
• 876498-09-8 2-heptyl-1-phenylbutane-1,3-dione 
• 6434-78-2 2-nonene 
• 420849-80-5 (2R,3S)-1-(3-hexyl-oxiranyl)-ethanone 
• 13058-45-2 3,4-epoxy-2-decanone 
• 693-54-9 Decan-2-one 
• 3013-10-3 trans--methyl-keton-2,4-dinitrophenylhydrazon 
• 1577-98-6 (E)-2-nonenoic acid 

Relevant academic research and scientific papers

Novel Benzo[a]quinolizidine Analogs Induce Cancer Cell Death through Paraptosis and Apoptosis

Paraptosis is nonapoptotic cell death characterized by massive endoplasmic reticulum (ER)- or mitochondria-derived vacuoles. Induction of paraptosis offers significant advantages for the treatment of chemotherapy-resistant tumors compared with anticancer drugs that rely on apoptosis. Because some natural alkaloids induce paraptotic cell death, a novel series of benzo[a]quinolizidine derivatives were synthesized, and their antiproliferative activity and ability to induce cytoplasmic vacuolation were analyzed. Structural optimization led to the identification of the potent compound 22b, which inhibited cancer cell proliferation in vitro and in vivo and profoundly facilitated paraptosis-like cell death and induced caspase-dependent apoptosis. Further investigation revealed that 22b-mediated vacuolation originated from persistent ER stress and upregulation of LC3B. Paraptosis induced by benzo[a]quinolizidine derivatives thus represents an alternative strategy for cancer chemotherapy.

Terminal olefins to linear α,β-unsaturated ketones: Pd(II)/hypervalent iodine co-catalyzed wacker oxidation-dehydrogenation

Development of a mild (35 C, no Bronsted acids) tandem Wacker oxidation-dehydrogenation of terminal olefins was accomplished using palladium(II) and hypervalent iodine co-catalysis. The reaction affords linear aryl and alkyl α,β-unsaturated ketones directly from readily available terminal olefins in good yields (average 75% per step) with excellent functional group tolerance and chemo- and stereoselectivities. The hypervalent iodine co-catalyst was found to be critical for dehydrogenation but was not effective as a stoichiometric oxidant.

Design, synthesis and antimycobacterial activities of 1-methyl-2-alkenyl- 4(1H)-quinolones

A series of 23 new 1-methyl-2-alkenyl-4(1H)quinolones have been synthesized and evaluated in vitro for their antimycobacterial activities against fast growing species of mycobacteria, such as Mycobacterium fortuitum, M. smegmatis and M. phlei. The compounds displayed good to excellent inhibition of the growth of the mycobacterial test strains with improved antimycobacterial activity compared to the hit compound, evocarpine. The most active compounds, which possessed chain length of 11-13 carbons at position-2 displayed potent inhibitory effects with an MIC value of 1.0 mg/L. In a human diploid embryonic lung cell line, MRC-5 cytotoxicity assay, the alkaloids showed weak to moderate cytotoxic activity. Biological evaluation of these evocarpine analogues on the less pathogenic fast growing strains of mycobacteria showed an interesting antimycobacterial profile and provided significant insight into the structure-activity relationships.

Gold-catalyzed highly regioselective oxidation of C-C triple bonds without acid additives: Propargyl moieties as masked α,β-unsaturated carbonyls

Gold-catalyzed intermolecular oxidations of internal alkynes have been achieved with high regioselectivities using 8-alkylquinoline N-oxides as oxidants and in the absence of acid additives. Synthetically versatile α,β-unsaturated carbonyls are obtained in good to excellent yields and with excellent E-selectivities. A range of functional groups such as THP, MOMO, N3, OTBS, and N-Boc are tolerated. This reaction allows α,β-unsaturated carbonyls to be masked as propargyl moieties, thus offering a practical solution to compatibility issues with these functional groups likely encountered in syntheses of complex structures.

L-proline-catalyzed one-pot three-component reaction for the synthesis of β-alkoxy ketones

β-Alkoxy ketones were prepared by a one-pot three-component reaction of aliphatic aldehydes, ketones, and alcohols catalyzed by L-proline. Steric effects on the reaction were studied with substituted ketones, aldehydes, and alcohols, and the results indicate that reactions employing methyl ketones, α-unsubstituted aliphatic aldehydes and methanol produce the β-alkoxy ketones in the best yields when L-proline is used as the catalyst. The reaction mechanism is discussed. Georg Thieme Verlag Stuttgart.

β′-Hydroxy-α,β-unsaturated ketones: A new pharmacophore for the design of anticancer drugs

A series of β′-hydroxy-α,β-unsaturated ketones were prepared by means of an iron(III) catalyzed domino process. The in vitro antiproliferative activities were examined in the human solid tumor cell lines A2780, SW1573, and WiDr. The results showed that β′

In situ generation of 2,3-allenolates in the coupling of secondary homopropargylic alcohols and aldehydes

A study on a novel oxonia [3,3]-sigmatropic rearrangement as competitive alternative pathway to the acetylenic Prins cyclization on the addition of secondary homopropargylic alcohols to aldehydes catalyzed by iron(III) is described. 'Ab initio' theoretica

Unsymmetrical unsaturated ketones from lactones and carboxylic acids in one step

A one-step transformation of γ- and δ-(spiro)lactones into γ,δ- and δ,ε-unsaturated ketones in the presence of carboxylic acids in the vapor phase at 400° over a supported manganese catalyst is reported for the first time. The scope of this new transformation is exemplified with a series of lactones, and a mechanistic rationale is proposed.

Acetyl chloride-ethanol brings about a remarkably efficient conversion of allyl acetates into allyl chlorides

AcCl-EtOH transforms primary and secondary allyl acetates into allyl chlorides that retain the olefinic bond in the more stable position. Whereas secondary allyl alcohols also react with almost the same efficacy as the acetates, the reactions of primary allyl alcohols that possess 1, 2-disubstituted alkenes are very slow. The products are isolated in high state of purity simply by removal of the volatiles.

A new protocol for a regioselective aldol condensation as an alternative convenient synthesis of β-ketols and α,β-unsaturated ketones

A general and convenient synthesis of β-ketols and α,β-alkenones has been achieved by a Knoevenagel condensation of a β-ketoacid with an aldehyde in aqueous medium. Saponification of a β-ketoester by an aqueous KOH 10% solution gives the potassium salt of the β-ketoacid, which is condensed in situ with an aldehyde at pH 7.8-8.0, at 60 °C for 5-6 h. The intermediate β-ketocarboxylate is smoothly decarboxylated in the reaction medium, giving the β-ketol in high yield (75-90%). Acidification of the reaction mixture at pH 1 and heating at 70 °C under vigorous stirring for 6 h, leads directly to the corresponding α,β-unsaturated ketone in good yield (65-75%).