96308-48-4

Upstream product

• 61815-42-7 (E)-1-Bromo-cyclooctene 
• 68-12-2 N,N-dimethyl-formamide 
• 64190-29-0 2-Benzenesulfinyl-1-oxa-spiro[2.7]decane 
• 19860-77-6 2-cyclooctene-1-methanol 
• 104489-07-8 (E)-1-(nitromethyl)cyclooct-1-ene 
• 42827-25-8 1-cyclooctenyllithium 
• 201230-82-2 carbon monoxide 
• 3806-59-5 1,3-cyclooctadiene 
• 4885-02-3 Dichloromethyl methyl ether 
• 127686-14-0 (1-cyclooctenyl)trimethylstannane 
• 162733-45-1 dibutyldi-1-cyclooctene-1-ylstannane 
• 162733-46-2 bis(1-cyclooctenyl)dimethylstannane 
• 28075-35-6 1-cyclooctenyl triflate 
• 2567-85-3 cyclooctanone p-tolylsulfonylhydrazone 

Downstream Products

• 96308-45-1 cyclooctene-1-carboxaldehyde tosylhydrazone 
• 1123-11-1 cyclonona-1,2-diene 
• 6573-52-0 cyclononyne 
• 96308-41-7 bicyclo<6.1.0>non-1(2)-ene 

Relevant academic research and scientific papers

Design, synthesis, and discovery of a novel CCR1 antagonist

The CC chemokines may play an important role in the pathogenesis of chronic inflammatory diseases including rheumatoid arthritis, and their effects are thought to be mediated through CCR1 receptors. Several nonpeptide CCR1 receptor antagonists that showed

Saegusa Oxidation of Enol Ethers at Extremely Low Pd-Catalyst Loadings under Ligand-free and Aqueous Conditions: Insight into the Pd(II)/Cu(II)-Catalyst System

A highly efficient and practical Pd(II)/Cu(OAc)2-catalyst system of Saegusa oxidation, which converts enol ethers to the corresponding enals with a number of diverse substrates at extremely low catalyst loadings (500 mol ppm) under ligand-free and aqueous conditions, is described. Its synthetic utility was demonstrated by large-scale applications of the catalyst system to important nature molecules. This work allows Saegusa oxidation to become a highly practical approach to preparing enals and also suggests new insight into the Pd(II)/Cu(II)-catalyst system for dehydrogenation of carbonyl compounds and decreasing Pd-catalyst loadings.

Enantioselective aziridination of cyclic enals facilitated by the fluorine-iminium ion Gauche effect

The enantioselective, organocatalytic aziridination of small, medium and macro-cyclic enals is reported using (S)-2-(fluorodiphenyl methyl)-pyrrolidine. Central to the reaction design is the reversible formation of a β-fluoroiminium ion intermediate, which is pre-organised on account of the fluorine-iminium ion gauche effect. This conformational effect positions the fluorine substituent synclinal-endo to the electropositive nitrogen centre thus benefiting from favourable stereoelectronic and electrostatic interactions (σC-H→σC-F*; F δ-···N+). Consequently, one of the shielding groups on the fluorine-bearing carbon atom is positioned above the π-system, forming the basis of an enantioinduction strategy. Treatment of this intermediate with a "nitrene" source furnished a series of novel, optically active aziridines (e.r. up to 99.5:0.5). Further derivatisation of the product aziridines gives facile access to various amino acid derivatives, including β-fluoroamino acids. Crystallographic analyses of both the aziridines and their derivatives are disclosed. Copyright

Synthesis and biological activity of enantiomeric pairs of 5-(alk-2-enyl)thiolactomycin and 5-[(E)-cycloalk-2-enylidenemethyl] thiolactomycin congeners

The title compounds were synthesized by the efficient route previously explored for the synthesis of enantiomeric pairs of thiolactomycin and its 3-demethyl derivative. These studies were carried out to prove the flexibility of the previously explored synthetic route to natural thiolactomycin (TLM) 1 and to examine the structure-activity relationship on the 5-position of 1. While all of the synthesized congeners lacked in vitro antibacterial activity, these studies led us to find 5-(alk-2-enyl)-TLM (ent-4d) which exhibits mammalian type I fatty acid synthase (FAS) inhibitory activity equal to that of C75, a potent inhibitor reported previously. It was also found that 5-[(E)-cycloalk-2- enylidenemethyl]-TLM (ent-5c) exhibited slightly less potent mammalian type I FAS inhibitory activity than C75.

Cyclic compounds and uses thereof

Compounds of general formula (1) R1—X1—W—X2—Z1—Z2—R2 or salts thereof, exhibiting preventive and therapeutic effects against HIV infectious diseases wherein R1is an optionally substituted five- or six-membered ring group; X1is a free valency or the like; W is a divalent group represented by, e. g., general formula (2) (wherein A and B are each an optionally substituted five- to seven-membered ring; E1and E4are each optionally substituted carbon or the like; E2and E3are each oxygen or the like; and a and b are each a single bond or a double bond); X2is a divalent group constituting a straight chain moiety; Z1is a divalent cyclic group or the like; Z2is a free valency or the like; and R2is optionally substituted amino or the like.

An efficient procedure for palladium-catalyzed hydroformylation of aryl/enol triflates

An efficient method for hydroformylation of aryl and enol trifluoromethanesulfonates is presented. Their reaction with carbon monoxide, trioctylsilane, and triethylamine in the presence of a catalytic amount of palladium acetate and 1,3-bis(diphenylphosphanyl)propane proceeds efficiently to provide a variety of aromatic and α,β-unsaturated aldehydes.

Synthesis of aromatic and αβ-unsaturated aldehydes by a friedel-crafts-like electrophilic destamylation using 1,1-dichloromethyl metyhyl ether

A mild and effective method for the preparation of a variety of aromatic (7a-m), heteroaromatic (7n-r), and α,β-unsaturated aldehydes (8a-f) is described. The reaction of trialkylaryl- (2a-o), heteroaryl- (2p-t), and 1-alkenylstannanes (4a-f and 5a-f) with dichloromethyl methyl ether (1, DCME) in the presence of aluminium trichloride followed by hydrolysis provides the corresponding aldehydes. In the case of arylstannanes the ipso-isomers are generally formed; the p-alde-hydes occur as side products. The electrophilic substitution of 1-alkenylstannanes with 1 leads to α,β-unsaturated aldehydes In an ipso- and stereospecific manner. A comparison of the leaving abilities of the stannyl and silyl groups shows a lower or even zero reactivity of the silyl-substituted compounds 8a-e towards the electrophile 1. In the silylstannylalkene 6c only the stannyl group reacts whereas the stannyl function remains unaffected in the product, aldehyde 11.

Synthesis with organoboranes V. Hydroxymethylation and formylation of cycloalkenes via allylic organopotassium and organoboron compounds

Allylic hydroxymethylation of cyclohexene and cyclooctene was achieved by metallation with trimethylsilylmethylpotassium followed by the reaction with formaldehyde. 1-Methylcycloalkenes were transformed into 2-methylenecycloalkane-1-methanols by the reaction of formaldehyde with allylic diethylboranes derived from these olefins via metallation-transmetallation.Conjugated cycloalkenecarboxaldehydes were obtained by oxidation of the hydroxymethylation products.

A Simple Method for Producing Cycloalkenyllithiums from Cycloalkanones via Reductive Lithiation of Enol Phenyl Thioethers

Cyclohexenyl, cycloheptenyl, and cyclooctenyl phenyl sulfides, readily prepared from the corresponding cycloalkanones, are reductively lithiated by lithium p,p'-di-tert-butylbiphenylide to produce cycloalkenyllithiums in good yields.

α,β-Epoxy Sulfoxides as Useful Intermediates in Organic Synthesis. X. An Improved Synthesis of α,β-Unsaturated Carbonyl Compounds from Carbonyl Compounds with Carbon Homologation through α,β-Epoxy Sulfoxides

Treatment of the α,β-epoxy sulfoxides derived from ketones and chloromethyl phenyl sulfoxide or 1-chloroalkyl phenyl sulfoxides with lithium perchlorate in the presence of tributylphosphine oxide in toluene at 110 deg C for about 1-3 h gave α,β-unsaturated aldehydes or α,β-unsaturated ketones in high yields.In contrast to these results, the α,β-epoxy sulfoxides derived from aldehydes did not give the desired α,β-unsaturated ketones.In this case, a sequential treatment of the α,β-epoxy sulfoxides with benzenethiolate and m-chloroperbenzoic acid afforded α-phenylsulfinylated ketones, which were heated in toluene at 110 deg C to give the desired enones in good overall yields.The oxidation of the α,β-unsaturated aldehydes obtained by this method gave α,β-unsaturated carboxylic acids in high yields.These procedures afforded a new method for the synthesis of α,β-unsaturated carbonyl compounds, including α,β-unsaturated esters, from carbonyl compounds with carbon homologation.