27644-03-7

Upstream product

• 26902-24-9 3-(benzyloxy)-3-methyl-1-butene 
• 5908-41-8 benzoyltrimethylsilane 
• 870-63-3 prenyl bromide 
• 1171-49-9 benzoyl-triphenyl-silane 
• 35189-96-9 3-methyl-2-butenylmagnesium chloride 
• 123290-13-1 phenyltriisopropylsilylmethanone 
• 100-52-7 benzaldehyde 
• 10276-04-7 3-methyl-1-phenylsulfanylbut-2-ene 
• 64135-15-5 diethyl (3-methylbut-2-en-1-yl) phosphate 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 18293-99-7 Prenyltrimethylsilane 
• 129813-21-4 2-(1,1-dimethyl-2-propenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1207865-76-6 4-(4-methyl-1-phenylpent-3-enyloxy)but-2-ynyl pivalate 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 

Downstream Products

• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 
• 61752-45-2 Z-1-phenylpent-3-en-1-one 
• 74157-93-0 trans-1-phenyl-3-penten-1-one 
• 4535-64-2 5-methyl-1-phenylhex-4-en-1-one 
• 4528-19-2 5-Methyl-1-phenyl-4-hexen-1-ol 
• 69815-01-6 4-methyl-1-phenylpentane-1,4-diol 
• 72486-22-7 4-Methyl-1-phenylpenta-1,3-diene 

Relevant academic research and scientific papers

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.

Catalytic asymmetric aldehyde prenylation and application in the total synthesis of (-)-rosiridol and (-)-bifurcadiol

Chiral phosphoric acid-catalyzed asymmetric aldehyde prenylation has been established using an α,α-dimethyl allyl boronic ester. The transformation provides expedient access to a wide array of aryl, heteroaryl, aryl-substituted alkenyl and primary and sec

Hydroxy-directed, fluoride-catalyzed epoxide hydrosilylation for the synthesis of 1,4-diols

Abstract A novel highly regioselective, fluoride-catalyzed hydrosilylation of β-hydroxy epoxides has been developed. The reaction is modular and applicable to the synthesis of a broad range of 1,4-diols. Fluoride is crucial for two reasons: First, it promotes the formation of a silyl ether (which contains a Si-H bond) and, second, it enables ring opening by an intramolecular SN2 reaction through activation of the silane. The reaction can be performed under air. A modular, convergent, and stereoselective synthesis of 1,4-diols by epoxide hydrosilylation has been developed (see scheme). The reaction occurs under fluoride catalysis, is high yielding, highly regioselective, and can be carried out on a large scale.

Highly regioselective and chemoselective titanocene mediated Barbier-type allylation reactions

Titanocene carboxylate 1 is an excellent chemoselective reagent for unprecedented α-regioselective Barbier-type reactions. It constitutes the first titanocene(iii) able to tolerate epoxides and readily reduced carbonyl compounds, such as aromatic and α,β-unsaturated aldehydes. The Royal Society of Chemistry.

Prins cyclization of α-bromoethers under basic conditions

α-Bromoethers have been found to undergo Prins-type cyclization under basic conditions and without the need to add a promoter. The products are those derived from a Markovnikov addition on the pendant alkene. However, the stereochemistry and even the structure of the products sometimes differ from those expected with the classical Lewis-acid-catalyzed Prins reaction of acetals.

Product selectivity control induced by using liquid-liquid parallel laminar flow in a microreactor

Product selectivity control based on a liquid-liquid parallel laminar flow has been successfully demonstrated by using a microreactor. Our electrochemical microreactor system enables regioselective cross-coupling reaction of aldehyde with allylic chloride via chemoselective cathodic reduction of substrate by the combined use of suitable flow mode and corresponding cathode material. The formation of liquid-liquid parallel laminar flow in the microreactor was supported by the estimation of benzaldehyde diffusion coefficient and computational fluid dynamics simulation. The diffusion coefficient for benzaldehyde in Bu4NClO4-HMPA medium was determined to be 1.32 × 10-7 cm2 s-1 by electrochemical measurements, and the flow simulation using this value revealed the formation of clear concentration gradient of benzaldehyde in the microreactor channel over a specific channel length. In addition, the necessity of the liquid-liquid parallel laminar flow was confirmed by flow mode experiments.

Chemoselective reaction system using a two inlet micro-flow reactor: Application to carbonyl allylation

A new strategy for chemoselective reaction using a two inlet micro-flow reactor is described. In this system, the combined use of suitable flow mode and corresponding cathode material enables chemoselective cathodic reduction to control the product regios

Pt-catalyzed tandem 1,2-acyloxy migration/intramolecular [3 + 2] cycloaddition of enynyl esters

(Formula Presented) A platinum-catalyzed tandem reaction involving enynyl ester isomerization and subsequent intramolecular [3 + 2] cyclization has been developed. This strategy provides an efficient approach to five-, six-, or seven-membered cyclic polyfunctional compounds. Copyright

New and stereoselective synthesis of 1,4-disubstituted buten-4-ols (homoallylic alcohol α-adducts) from the corresponding γ-isomers (3,4-disubstituted buten-4-ols) via an acid-catalyzed allyl-transfer reaction with aldehydes

The γ-adducts of homoallylic alcohols 3, derived from aldehydes via the usual reaction with common allylic metals 1, were converted to the corresponding α-adducts 6 by an acid-catalyzed allyl-transfer reaction. In the allyl-transfer reaction, anti-and syn

Solvolysis of 1-[trans-2-(m- Orp-Substituted Phenyl)cyclopropyl]- 1-methylethyl p-Nitrobenzoates

The solvolyses of 1-[trans-2-(m- or p-substituted phenyl)cyclopropyl]-1-methylethyl p-nitrobenzoates in 80% aqueous acetone have been studied with regard to both reactivity and product composition. For the less reactive substituents such as m-Br, m-Cl, and m-CF3, the solvolysis products were the corresponding 2-(2-arylcyclopropyl)-2-propanol, indicating the cyclopropylmethyl cation intermediate. The ring-opened products increased as the electron-donating ability of the substituents increased. The application of the Yukawa-Tsuno equation to the reactivity afforded a ρ value of -1.43 and r value of 0.59 with a correlation coefficient of 0.997. A large value of r indicates the presence of the allylic cation intermediate where much more charge develops at the benzylic carbon for the derivatives with electron-donating substituents than is the case for the cyclopropylmethyl cation intermediate. Thus the solvolysis reaction proceeds via two independent pathways: one has a cyclopropyl cation intermediate and the other has a homoallylic cation intermediate.