27259-09-2

Upstream product

• 123620-68-8 1-acetyl-2-methyl-aziridine 
• 61307-38-8 1-heptynylmagnesium bromide 
• 42017-07-2 1-heptynyllithium 
• 540-88-5 acetic acid tert-butyl ester 
• 628-71-7 1-Heptyne 
• 105-46-4 sec-Butyl acetate 
• 141-78-6 ethyl acetate 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 109-99-9 tetrahydrofuran 
• 2809-67-8 oct-2-yne 
• 67-66-3 chloroform 
• 26547-25-1 non-3-yn-2-ol 
• 127-19-5 N,N-dimethyl acetamide 

Downstream Products

• 1104393-74-9 (Z)-4-(dimethyl((4-trifluoromethyl)benzyl)silyl)non-3-en-2-one 
• 1104393-73-8 (Z)-3-(dimethyl-(2,3,4,5,6-pentafluorobenzyl)silyl)non-3-en-2-one 
• 937800-13-0 (R)-1-methoxy-4-((non-8-yn-2-yloxy)methyl)benzene 
• 110-43-0 n-pentyl methyl ketone 
• 64-19-7 acetic acid 
• 67-64-1 acetone 
• 142-62-1 hexanoic acid 
• 80387-31-1 (3E,5E)-nona-3,5-dien-2-one 

Relevant academic research and scientific papers

Ynones Merge Activation/Conjugate Addition of Chalcogenoborates ArE-Bpin (E=Se, S)

The "pull-push" effect of the Bpin moiety in ArE-Bpin reagents (E=Se, S) is demonstrated by the Lewis acid interaction with the carbonyl group of ynones and the concomitant delivery of ArSe or ArS to the electron-deficient alkyne with impressive stereosel

Si-based benzylic 1,4-rearrangement/cyclization reaction

(Chemical Equation Presented) The trans-selective hydrosilylation of ynones (1) yields ss-silylated enones (2) that undergo a benzylic 1,4-rearrangement/cyclization reaction in the presence of base, yielding 2,5-dihydro-1,2-oxasiloles (3).

Synthetic studies on macrolactin A: Construction of C4-C24 fragment

(Chemical Equation Presented) The preparation of the C4-C24 fragment of the macrolactin A is described. The adopted synthetic strategy involves two isomerizations to selectively construct the (8E,10Z) and (16E,18E) dienes, using a sequential Claisen rearrangement/allene isomerization and a Ph 3P-catalyzed isomerization of an yne-one, respectively.

Polymer-supported selenol esters as useful acylating reagents. Application to α, β-acetylenic ketones synthesis

Three novel polystyrene supported selenol esters were synthesized and used as acyl transfer agents to prepare α, β-acetylenic ketones by reaction with alkynylcoppers.

An improved synthesis of dialkylcyclopropenones

Dialkylcyclopropenones are formed in high yields when alkynes are treated with chloroform-butyllithium in THF at - 78 °C followed by acidic hydrolysis of the dichlorocyclopropene intermediates at low temperatures.

New synthetic applications of organotin compounds: Synthesis of stereodefined 2-iodo-2-alkenones, 2-substituted (E)-2-alkenones and 2-methyl-2-cycloalkenones

Stereoisomeric mixtures of 3-iodo-3-nonen-2-one, 8a, 2-iodo-1-phenyl-2-octen-1-one, 8b, 2-iodo-1,3-diphenyl-2-propen-1-one, 8c, as well as (Z)-3-iodo-4-phenyl-3-buten-2-one, 8d, have been efficiently synthesized by a reaction sequence involving a Pd-catalyzed reaction between the corresponding 1-alkynyl ketones, 10, and Bu3SnH followed by iododestannylation. Stereomutation experiments carried out in the presence of daylight and using catalytic amounts of I2 showed that the Z stereoisomers of 8a, 8b and 8c, which could be separated by MPLC on silica gel from the corresponding E stereoisomers, as well as compound (Z)-8d were more stable than their E stereoisomers. Compounds 8a-d underwent Pd-catalyzed cross-coupling reactions with C6H5SnMe3, CH2=CH-SnBu3 and SnMe4 providing an efficient route to the corresponding 2-substituted 2-alkenones, 13. However, the Pd-catalyzed reaction between (Z)-8c and PhSnMe3 afforded a mixture of the expected cross-coupled product, (E)-13f with the compound derived from methyl transfer, (E)-13e. The couplings involving (Z)-8a, (Z)-8b, (Z)-8c and (Z)-8d proceeded with clean retention of stereochemistry, but the Pd-catalyzed reaction between (E)-8c and SnMe4 afforded a stereoisomeric mixture of 13e. On the contrary, the coupling between (E)/(Z)-8b and SnMe4 produced stereoisomerically pure (E)-13c. Two 2-iodo-2-cycloalkenones, i.e. compounds 18a and 18b, also reacted with SnMe4, in the presence of a Pd catalyst, to give the corresponding 2-methyl-2-cycloalkenones, 19a and 19b, respectively, in satisfactory yields. Compound 19b represents a very useful precursor to methylenomycin B, 9.

CONVENIENT KETONE SYNTHESIS VIA N-ACYLAZIRIDINES

N-Acylaziridines couple efficiently with organolithium and Grignard reagents to produce ketones in high yields.

PALLADIUM-CATALYZED ACYLATION OF ORGANOZINCS AND OTHER ORGANOMETALLICS AS A CONVENIENT ROUTE TO KETONES

The reaction of organozincs with acyl chlorides catalyzed by palladium-phosphine complexes, e.g., Pd(PPh3)4, provides a highly general and convinient route to ketones.