81417-97-2

Upstream product

• 7051-34-5 cyclopropylcarbinyl bromide 
• 2043-61-0 cyclohexanecarbaldehyde 
• 7103-09-5 4-but-1-enylmagnesium bromide 
• 2100-17-6 4-pentenal 
• 931-50-0 cyclohexylmagnesium bromide 
• 626-62-0 Cyclohexyl iodide 
• 1344115-80-5 CH₂CH₂CHCH₂BO₂(CH₂)3 
• 5162-44-7 1-bromo-4-butene 

Downstream Products

• 1206670-38-3 C₂₃H₃₅NO₄S 
• 1010081-72-7 (E)-6-cyclohexyl-6-hydroxyhex-2-enal 
• 200641-13-0 (E)-1-Cyclohexyl-5-(toluene-4-sulfonyl)-pent-4-en-1-ol 
• 101567-04-8 (RS)-5-cyclohexyl-3-methylenedihydrofuran-2(3H)-one 
• 727665-03-4 1-cyclohexylpent-4-enyl acetate 
• 727665-55-6 (1-azidopent-4-enyl)cyclohexane 
• 190730-19-9 1-Cyclohexyl-4-iodo-5-(toluene-4-sulfonyl)-pentan-1-ol 

Relevant academic research and scientific papers

Organocatalytic synthesis of polysubstituted tetrahydrofurans from alkenes

A novel, organocatalytic and environmentally friendly protocol for the synthesis of polysubstituted tetrahydrofurans from trivial starting materials has been described. By employing 2,2,2-trifluoroacetophenone-mediated oxidation, which utilizes H2O2 as a green oxidant, we introduce a sustainable procedure that embraces the principles of green chemistry for the production of substituted tetrahydrofurans in high to excellent yields and tolerates a wide range of substitution patterns.

Boron carboxylate catalysis of homoallylboration

Boron tris(trifluoroacetate) is identified as the first effective catalyst for the homoallyl- and homocrotylboration of aldehydes by cyclopropylcarbinylboronates. NMR spectroscopic studies and theoretical calculations of key intermediates and transition states both suggest that a ligand-exchange mechanism, akin to our previously reported PhBCl 2-promoted homoallylations, is operative. Our experimental and theoretical results also suggest that the catalytic activity of boron tris(trifluoroacetate) might originate from more facile catalytic turnover of the trifluoroacetate ligands (in agreement with DFT calculations) or from a lower propensity for formation of off-pathway reservoir intermediates (as observed by 1H NMR). This work shows that carboxylates are viable catalytic ligands for homoallyl- and homocrotylations of carbonyl compounds and opens the door to the development of catalytic asymmetric versions of this transformation.

Au-catalyzed cyclization of monoallylic diols

The Ph3PAuCl/AgOTf-catalyzed cyclization of monoallylic diols to form tetrahydropyrans is reported. The reactions proceed rapidly at temperatures as low as -78° C with catalyst loadings as low as 0.1 mol % to provide the products in 79-99% yield. A broad range of structurally diverse substrates perform well in the reaction. When 2,6-disubstituted tetrahydropyrans are produced, the reaction is highly diastereoselective for the 2,6-cis product.

Indium-copper and indium-silver mediated Barbier-Grignard-type alkylation reaction of aldehydes using unactivated alkyl halides in water

(Chemical Equation Presented) An efficient method has been developed for the Barbier-Grignard-type alkylation reaction of aldehydes (including aliphatic version) using unactivated alkyl halides in water in the presence of an In/CuI/I2 or In/AgI/I2 system. The reactions proceeded more efficiently in water than in organic solvent. In, CuI or AgI, and I 2 were all essential for the efficient progress of the reactions. A radical-type reaction mechanism was studied and proposed by using 4-pentenal as substrate.

A facile method for synthesis of 5-hydroxypentene via sonochemical barbier reaction

A series of 5-hydroxypentenes was synthesized from the reaction mixture of Mg powder, 1,2-dibromoethane, 4-bromobutene and aldehydes in THF under ultrasound. This sonochemical Barbier reaction provides a simple and alternative method for preparation of 5-hydroxypentene instead of the allylating reagent with epoxide.

Dibromomethane as one-carbon source in organic synthesis: A versatile methodology to prepare the cyclic and acyclic α-methylene or α-keto acid derivatives from the corresponding terminal alkenes

Ozonolysis of mono-substituted alkenes A-1 followed by reacting with a preheated mixture of CH2Br2-Et2NH affords α-substituted acroleins A-2 in good yields. Under very mild reaction conditions, these α-substituted acroleins A-2 can be easily converted to α-methylene esters A-4, which could be further converted to the corresponding α-keto esters A-5. This methodology can be also applied to the preparation of α-methylene lactones B-4, α-methylene lactams, and α-keto lactones B-5 with various ring sizes.

A Stereoselective Approach to 2,6-Disubstituted Tetrahydropyrans by Conjugate Addition Reactions of Vinyl Sulfones

A highly stereoselective synthesis of cis-2,6-disubstituted tetrahydropyrans from functionalised 5-hexen-1-ols has been developed. Free radical addition of para-toluenesulfonyl iodide to the hexenol and DBU-mediated elimination of HI from the intermediate β-iodosulfones gives vinyl sulfones: subsequent conjugate addition of the potassium alkoxide leads to a highly stereoselective (≥30:1) cyclisation.

Photoreactions of Phenyl-Substituted N-(Pent-4-enyl-1-oxy)pyridine-1(1H)-thiones

A series of hitherto unknown N-(pent-4-enyl-1-oxy)pyridine-2(1H)-thiones (6) were prepared from substituted pent-4-enyl tosylates or benzylic chlorides.On irradiation with incandescent light heterocycles 6 liberated alkoxy radicals 2, which were studied for rearrangement reactions.Surprisingly, all transformations involving the 1-phenylpent-4-enyl-1-oxy radical (2a), for example, to give the substituted thioether 8, 2-bromomethyl-5-phenyltetrahydrofuran (11), or the tetrahydrofuran 14a, were not stereoselective.On the other hand 2-, 3-mono-, and 1,5-disubstituted pent-4-enyl-1-oxy radicals 2d-e and 2g cyclized in good yields and with good to excellent stereoselectivities to give the corresponding 2,4-cis- and 2,3-trans-phenyltetrahydrofurfuryl radicals 3d-e, and the trans-2-benzyl-5-methyl substituted intermediate 3g.The major reaction mode of the 4-phenylpent-4-enyl-1-oxy radical (2f) was the 6-endo cyclization, which afforded 3-phenyltetrahydropyran (13f) as the major product (endo:exo=93:7) after trapping with hydrogen donors.According to the experimental data of the present study, the unusual reactivity of the 1-phenylpent-4-enyl-1-oxy radical (2a) in 5-exo-trig ring closures could be caused by a coplanar arrangement of the benzyloxy moiety in the transition state of the cyclization.This interaction would lock the radical center in 2a in a preferred conformation, which would result in similar steric effects for both cis- and trans-cyclizations. - Keywords: alkoxy radicals; cyclizations; pyridinethiones; radicals; tetrahydrofurans

A Convenient Large-Scale Synthesis of Cyclobutyl Halides

An improved method for the preparation of multigram quantities of cyclobutyl halides is described.The Grignard reactivity of these halides is also discussed.