27644-02-6

Upstream product

• 22089-60-7 benzyl prenyl ether 
• 100-52-7 benzaldehyde 
• 870-63-3 prenyl bromide 
• 36934-17-5 Diethyl(3-methyl-2-butenyl)-borane 
• 104108-29-4 prenyl tributylstannane 
• 5908-41-8 benzoyltrimethylsilane 
• 35189-96-9 3-methyl-2-butenylmagnesium chloride 
• 123290-13-1 phenyltriisopropylsilylmethanone 
• 72863-21-9 (dimethyl-1,1 propene-2 yl) sulfonyl-1 methyl-4 benzene 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 116504-03-1 prenyl ethyl carbonate 
• 106625-71-2 ethyl (2-methylbut-3-en-2-yl) carbonate 
• 62894-04-6 phenyl prenyl ketone 
• 100-42-5 styrene 

Downstream Products

• 27644-03-7 4-methyl-1-phenyl-pent-3-en-1-ol 
• 68705-88-4 6-methyl-1-phenyl-hept-5-en-3-ol 
• 62894-04-6 phenyl prenyl ketone 
• 1412901-52-0 2,2-dimethyl-1-phenylbut-3-en-1-yl acetate 
• 1616603-31-6 2,2-dimethyl-1-phenylbut-3-en-1-one acetyloxime 
• 1428236-05-8 4,4,5-trimethyl-3-phenyl-4,5-dihydroisoxazole 
• 62893-42-9 2-methyl-2-oxiranyl-1-phenyl-propan-1-ol 

Relevant academic research and scientific papers

Highly stereoselective allylation of aldehydes with pentacoordinate allylsilicates in hydroxylic media. Discrimination between linear and α-branched alkanals1

Allylation of aldehydes with allyltrifluorosilanes in the presence of a wide variety of hydroxy compounds and triethylamine gave the corresponding homoallyl alcohols in regio- and stereospecific manner. Pentacoordinate allylsilicates are suggested as inte

Carbonyl allylation in the absence of preformed allyl metal reagents: Reverse prenylation via iridium-catalyzed hydrogenative coupling of dimethylallene

Iridium-catalyzed hydrogenation of dimethylallene in the presence of aromatic, heteroaromatic, and aliphatic carbonyl electrophiles 1a-12a delivers products of reverse prenylation 1b-12b. Reductive coupling of dimethyl allene to aldehyde 8a under an atmosphere of deuterium provides deuterio-8b. As revealed by 2H NMR analysis, deuterium incorporation is observed at the vinylic position (80% 2H). Unlike established methods for carbonyl allylation, the present protocol circumvents the use of stoichiometrically preformed organometallic reagents. Copyright

An improved and practical synthesis route to antiproliferative (±)-shikonin and its O-acyl derivatives

Shikonin and its O-acyl derivatives are attracting increasing levels of attention among medicinal chemists due to their potencies as highly selective cytotoxic agents against cancer cells. However, providing a large number of shikonin-related samples by organic synthesis remains challenging. In the present study, we developed an improved and practical synthesis route to shikonin derivatives by olefin metathesis that has enabled the gram-scale preparation of a prenylated tetramethylnaphthazaline, a key intermediate in the synthesis of shikonin. In addition, a method for the selective cleavage of the acyl protecting groups at the phenolic positions of tri-O-acylated shikonins has been developed that provides concise routes to diverse O-acylshikonin derivatives.

Indium(I)/CuFe2O4 Reagent for Allylation of Carbonyls and Epoxide Rearranged Carbonyls

Abstract: Indium(I)/CuFe2O4 reagent forcarbonyl allylation and epoxide rearranged carbonyl allylation is proposed forformation of homoallylic alcohols. The In(I) reagent in combination withcatalytic amount of CuFe2O4support in situ formation of nucleophilicallylic indium from allyl halide in THF medium. Nucleophilic allylic indiumspecies react with carbonyls to form homoallyl alcohols in good to excellentyields. Under the presented reaction conditions arylepoxides undergo smoothrearrangement into aldehydes that are also allylated with formation of homoallylalcohols. The process is highly efficient and tolerates different functionalgroups.

Method for synthesizing polysubstituted alpha, beta unsaturated ketones

The invention particularly relates to a method for synthesizing polysubstituted alpha, beta unsaturated ketones. The method comprises the following steps: 1, adding Ni(cod), an N-heterocyclic carbene ligand, Cs2CO3 and a beta, gamma unsaturated ketone into a non-polar aprotic organic solvent, and mixing to obtain a mixture; 2, adding the mixture obtained in the step 1 into a dried container, reacting for 10-40 hours at the reaction temperature of 120-180 DEG C, and cooling to room temperature after the reaction is finished, so as to obtain a crude product; 3, purifying. According to the method, cheap Ni(cod) is adopted as a catalyst, carbon-carbon bonds are activated by a transition metal, power is provided for the reaction through isomerization of double bonds, the synthesis methodis simple, the substrates are stable and cheap, the reaction is less limited by the substrate, and the substrates are wide in application range.

Catalytic Allylation of Aldehydes Using Unactivated Alkenes

Simple feedstock organic molecules, especially alkenes, are attractive starting materials in organic synthesis because of their wide availability. Direct utilization of such bulk, inert organic molecules for practical and selective chemical reactions, however, remains limited. Herein, we developed a ternary hybrid catalyst system comprising a photoredox catalyst, a hydrogen-atom-transfer catalyst, and a chromium complex catalyst, enabling catalytic allylation of aldehydes with simple alkenes, including feedstock lower alkenes. The reaction proceeded under visible-light irradiation at room temperature and with high functional group tolerance. The reaction was extended to an asymmetric variant by employing a chiral chromium complex catalyst.

Photoredox Ni-Catalyzed Branch-Selective Reductive Coupling of Aldehydes with 1,3-Dienes

We report here a Ni-catalyzed reductive coupling of aldehydes with widely available 1,3-dienes under visible-light photoredox dual catalysis. The homoallyic alcohols are obtained in broad scope with complete branched regioselectivity. Hantzsch ester is used as the hydrogen radical source to oxidize low-valent nickel salt affording Ni-H species. Preliminary mechanistic studies indicate a successive single-electron transfer (SET) pathway and the generation of a key π-allylnickel intermediate via Ni-H insertion of 1,3-diene in this synergistic catalytic process.

Silyl-Group-Directed Linear-Selective Allylation of Carbonyl Compounds with Trisubstituted Allylboronates Using a Copper(I) Catalyst

A copper(I)-catalyzed linear-selective allylation of carbonyl compounds with trisubstituted allylboronates has been achieved by capitalizing on the electronic and steric effects of silyl groups. This reaction provides stereodefined trisubstituted homoallyl alcohol derivatives that bear a synthetically useful alkenyl silane moiety. The results of a computational study suggested that the silyl directing group thermodynamically stabilizes the sterically hindered allylcopper(I) intermediate and kinetically facilitates the carbonyl allylation path for the linear product by lowering the energy of its transition state.

Copper-Catalyzed Diamination of Alkenes of Unsaturated Ketohydrazones with Amines

A convenient copper-catalyzed intra-/intermolecular diamination of β,γ-unsaturated hydrazones has been developed with simple amines as external amine sources. The protocol enables efficient access to various nitrogen-containing pyrazolines under mild reaction conditions.

Copper-Promoted 6- endo-trig Cyclization of β,γ-Unsaturated Hydrazones for the Synthesis of 1,6-Dihydropyridazines

A novel and efficient strategy for the synthesis of 1,6-dihydropyridazines via copper-promoted 6-endo-trig cyclization of readily available β,γ-unsaturated hydrazones have been developed. A series of 1,6-dihydropyridazines have been synthesized by this method with good yields, high functional group tolerance, and remarkable regioselectivity under mild conditions. Importantly, the 1,6-dihydropyridazines can be efficiently converted to biologically important pyridazines in the presence of NaOH.