72360-69-1

Upstream product

• 67-56-1 methanol 
• 67471-39-0 1-(p-chlorophenyl)-1-methoxyethene 
• 99-91-2 para-chloroacetophenone 
• 77-76-9 2,2-dimethoxy-propane 
• 149-73-5 trimethyl orthoformate 
• 1073-67-2 4-vinylbenzyl chloride 
• 22454-63-3 4'-Chloracetophenon-(4-phenylsemicarbazon) 

Downstream Products

• 112082-98-1 1-(4-chlorophenyl)vinyl isopropyl ether 
• 99-91-2 para-chloroacetophenone 
• 67-56-1 methanol 
• 20001-59-6 1-(4-chlorophenyl)-ethyl methyl ether 
• 1190071-13-6 1-(1-butylthio)-1-(4-chlorophenyl)ethane 
• 1372713-43-3 1,1,1-trichloro-4-(4-chlorophenyl)-3-buten-2-one 
• 67471-39-0 1-(p-chlorophenyl)-1-methoxyethene 
• 1176756-84-5 methyl 2,2-dimethyl-3-(p-chlorophenyl)-3-butenoate 
• 868662-44-6 4-[3-(4-chlorophenyl)-5-hydroxy-5-trifluoromethyl-4,5-dihydro-1H-pyrazol-1-yl]-7-chloroquinoline 
• 161636-14-2 (Z)-4-(4-Chloro-phenyl)-1,1,1-trifluoro-4-methoxy-but-3-en-2-one 

Relevant academic research and scientific papers

Development and Mechanistic Studies of the Iridium-Catalyzed C?H Alkenylation of Enamides with Vinyl Acetates: A Versatile Approach for Ketone Functionalization

Ketone functionalization is a cornerstone of organic synthesis. Herein, we describe the development of an intermolecular C?H alkenylation of enamides with the feedstock chemical vinyl acetate to access diverse functionalized ketones. Enamides derived from various cyclic and acyclic ketones reacted efficiently, and a number of sensitive functional groups were tolerated. In this iridium-catalyzed transformation, two structurally and electronically similar alkenes—enamide and vinyl acetate—underwent selective cross-coupling through C?H activation. No reaction partner was used in large excess. The reaction is also pH- and redox-neutral with HOAc as the only stoichiometric by-product. Detailed experimental and computational studies revealed a reaction mechanism involving 1,2-Ir-C migratory insertion followed by syn-β-acetoxy elimination, which is different from that of previous vinyl acetate mediated C?H activation reactions. Finally, the alkenylation product can serve as a versatile intermediate to deliver a variety of structurally modified ketones.

Formation of Acetals and Ketals from Carbonyl Compounds: A New and Highly Efficient Method Inspired by Cationic Palladium

The development of a new, highly efficient, and simple method for masking carbonyl groups as acetals and ketals is described. This methodology relies on the nature of the palladium catalyst to direct the acetalization/ketalization reaction. This new protocol is mild and proceed with a very low catalyst loading at ambient temperatures. The method has been extended to a wide variety of different carbonyl compounds with various steric encumbrances to form the corresponding acetals and ketals in excellent yields.

Silver-Catalyzed Olefination of Acetals and Ketals with Diazoesters to β-Alkoxyacrylates

The first silver-catalyzed reaction of acetals or ketals with diazoesters leading to trisubstituted or tetrasubstituted β-alkoxyacrylates is now reported. A broad range of acetals and ketals bearing different substituents is compatible with this protocol and thus provides an attractive approach for the synthesis of complex β-alkoxyacrylates. The power of this method was further demonstrated by the successful synthesis of picoxystrobin, which is one of the most popular agricultural fungicides commercialized by Dupont.

Highly efficient acetalization of carbonyl compounds catalyzed by anilin-aldehyde resin salts

A mild procedures for the syntheses of ethylene acetals and dimethyl acetals from the corresponding aldehydes and ketones catalyzed by 1mol% of anilinealdehyde resin salts are described. This method is also useful for the synthesis of dimethyl acetals of diaryl ketones.

Anodic cleavage of several ketone N-phenylsemicarbazones into methyl N-phenylcarbamate and the corresponding dimethyl acetals

Several ketone N-phenylsemicarbazones were electrooxidized in the presence of potassium iodide and a base using methanol as the solvent to give nearly commensurate amounts of methyl N-phenylcarbamate and the corresponding dimethyl acetals. Continuous evolution of gaseous nitrogen was observed from the anolyte during the electrooxidation. The reactions were carried out under very mild reaction conditions and are presumed to proceed through a four-electron oxidation process, in which the iodide ion plays an important role as an electron carrier.

A novel approach to the practical synthesis of sulfides: An InBr 3-Et3SiH catalytic system promoted the direct reductive sulfidation of acetais with disulfides

We have demonstrated a facile and direct synthesis of sulfide derivatives using acetais and ketals, derived, from aromatic/ conjugated, aldehydes and aromatic ketones, with disulfides and the InBr3-Et3SiH reducing system., We also succeeded in developing an unprecedented one-pot preparation of an aliphatic sulfide from a disulfide and an aliphatic acetal. (Wiley-VCH Verlag GmbH & Co. KGaA.

Pd(II)-catalyzed conversion of styrene derivatives to acetals: Impact of (-)-sparteine on regioselectivity

Pd[(-)-sparteine]Cl2 catalyzes the formation of dialkyl acetals from styrene derivatives with Markovnikov regioselectivity. The substrate scope of this reaction has been investigated, and initial mechanistic studies indicate that the reaction proceeds through an enol ether intermediate and a Pd-hydride.

Antimalarial activity of 4-(5-trifluoromethyl-1H-pyrazol-1-yl)-chloroquine analogues

The antimalarial activity of chloroquine-pyrazole analogues, synthesized from the reaction of 1,1,1-trifluoro-4-methoxy-3-alken-2-ones with 4-hydrazino-7-chloroquinoline, has been evaluated in vitro against a chloroquine resistant Plasmodium falciparum clone. Parasite growth in the presence of the test drugs was measured by incorporation of [3H]hypoxanthine in comparison to controls with no drugs. All but one of the eight (4,5-dihydropyrazol-1-yl) chloroquine 2 derivatives tested showed a significant activity in vitro, thus, are a promising new class of antimalarials. The three most active ones were also tested in vivo against Plasmodium berghei in mice. However, the (pyrazol-1-yl) chloroquine 3 derivatives were mostly inactive, suggesting that the aromatic functionality of the pyrazole ring was critical.

Tri-n-butylstannyl chloride-sodium cyanoborohydride mediated regioselective reductive demethoxylation of alkyl methyl ketals

A regioselective reductive demethoxylation of alkyl methyl ketals employing sodium cyanoborohydride in the presence of a catalytic amount of tri-n-butyltin chloride as Lewis acid is described.

A mild and simple procedure for the reductive cleavage of acetals and ketals

A convenient, mild and simple procedure, employing sodium cyanoborohydride in the presence of either catalytic or stoichiometric amount of boron trifluoride etherate in dry THF, for the reductive cleavage of the acetals and ketals is described.