135663-93-3

Upstream product

• 135663-97-7 1-phenylbut-3-yn-2-ol 
• 108-05-4 vinyl acetate 
• 135663-93-3 1-phenyl-3,4-pentadien-2-ol 
• 122-78-1 phenylacetaldehyde 
• 14657-29-5 tetrapropadienyl stannane 
• 624-65-7 2-propynyl chloride 
• 18295-60-8 allenylmagnesium bromide 
• 106-96-7 propargyl bromide 
• 50-00-0 formaldehyd 

Downstream Products

• 127559-61-9 (-)-1-phenyl-3,4-pentadien-2-ol 
• 135664-04-9 Acetic acid (R)-1-benzyl-buta-2,3-dienyl ester 
• 135664-04-9 Acetic acid (S)-1-benzyl-buta-2,3-dienyl ester 
• 1039769-87-3 2-ethyl-3-(methoxycarbonyl)-4-(5'-phenyl-1',3'-pentadien-3'(E)-2'-yl)-2,5-dihydrofuran 
• 1039769-81-7 3-butyl-2-(p-nitrophenyl)-4-(5'-phenyl-1',3'-pentadien-3'(E)-2'-yl)-2,5-dihydrofuran 
• 1039769-84-0 3-butyl-2-(o-chlorophenyl)-4-(5'-phenyl-1',3'-pentadien-3'(E)-2'-yl)-2,5-dihydrofuran 
• 1039769-75-9 3-butyl-2-methyl-4-(5'-phenyl-1',3'-pentadien-3'(E)-2'-yl)-2,5-dihydrofuran 
• 1039769-89-5 3-(methoxycarbonyl)-2-pentyl-4-(5'-phenyl-1',3'-pentadien-3'(E)-2'-yl)-2,5-dihydrofuran 
• 1039769-77-1 3-butyl-2-phenyl-4-(5'-phenyl-1',3'-pentadien-3'(E)-2'-yl)-2,5-dihydrofuran 
• 1039769-91-9 2-butyl-3-phenyl-4-(5'-phenyl-1',3'-pentadien-3'(E)-2'-yl)-2,5-dihydrofuran 
• 1039769-96-4 (S)-3-butyl-2-methyl-4-(5'-phenyl-1',3'-pentadien-3'(E)-2'-yl)-2,5-dihydrofuran 
• 1361252-02-9 (R)-2-benzyl-2,5-dihydrofuran 
• 1388792-15-1 (S)-2-benzyl-2,5-dihydrofuran 
• 1361251-89-9 (S)-1-phenylpenta-3,4-dien-2-ol 

Relevant academic research and scientific papers

Cobalt-Catalyzed C8-Dienylation of Quinoline-N-Oxides

An efficient Cp*CoIII-catalyzed C8-dienylation of quinoline-N-oxides was achieved by employing allenes bearing leaving groups at the α-position as the dienylating agents. The reaction proceeds by CoIII-catalyzed C?H activation of qui

Synthesis, characterization of active Sn(0), and its application in selective propargylation of aldehyde at room temperature in water

Active Sn(0) particles are synthesized in high yields by the chemical reduction of the blue-black stannous oxide using freshly prepared sodium stannite solution as reducing agent at 40 °C and 60 °C. The Sn(0) particles are characterized using powder XRD, SEM, and DSC. The as-synthesized Sn(0) particles are applied as reagent for the regioselective synthesis of homopropargyl alcohols from propargyl bromide and aldehydes in distilled water at room temperature (in 50%-84% yields). No assistance of heat, microwave, ultrasound, organic co-solvent, co-reagent, or inert atmosphere is required for this reaction. The propargylation reaction is highly chemoselective towards aldehyde over other less electrophilic carbonyl functional groups such as ketone, amide, and carboxylic acid. Our in-house synthesized homopropargyl alcohols can be used to synthesize conjugated 1,3-diynes.

Highly stereoselective kinetic resolution of α-allenic alcohols: An enzymatic approach

A highly efficient lipase AK-catalyzed direct kinetic resolution of a variety of α-allenic alcohols was developed. With the complementary to previous studies, the current reaction system is effective on a broad range of substituents (R1) at C(1), such as alkyl, aryl, alkenyl, and alkynyl groups. The Jones-Burgess empirical model was modified to interpret the reversed selectivity during the acetylation of secondary alcohol. The methyl group at C(2) of allenic alcohols implied a small structural adjustment in the catalytic triad of lipase AK, representing a potential direction for future site-directed mutagenesis.

Enzyme- and Ruthenium-Catalyzed Enantioselective Transformation of α-Allenic Alcohols into 2,3-Dihydrofurans

An efficient one-pot method for the enzyme- and ruthenium-catalyzed enantioselective transformation of α-allenic alcohols into 2,3-dihydrofurans has been developed. The method involves an enzymatic kinetic resolution and a subsequent ruthenium-catalyzed c

CuI-catalyzed synthesis of functionalized terminal allenes from 1-alkynes

Relative to our original protocol that uses CuI (0.5 equiv.), paraformaldehyde (2.5 equiv.), and dicyclohexylamine (1.8 equiv.), a facile and efficient protocol for the gram-scale synthesis of functionalized terminal allenes by using CuI (7.5-10 mol-%), p

Chiral silver phosphate-catalyzed cycloisomeric kinetic resolution of α-allenic alcohols

A kinetic resolution of α-allenic alcohols is realized through chiral silver phosphate-catalyzed cycloisomerization with high stereoselectivity (selectivity factor up to 189) and tolerance of a variety of functional groups. A mechanistic model is proposed to interpret the origin of the high stereoselectivity and broad substrate scope.

Efficient synthesis of 3-chloromethyl-2(5H)-furanones and 3-chloromethyl- 5,6-dihydropyran-2-ones via the PdCl2-catalyzed chlorocyclocarbonylation of 2,3- or 3,4-allenols

(Chemical Equation Presented) A mild and efficient methodology involving PdCl2-catalyzed chlorocyclocarbonylation of 2,3- or 3,4-allenols with CuCl2 for the synthesis of 3-chloromethyl-2(5H)-furanones and 3-chloromethyl-5,6-dihydropyran-2-ones was developed. This reaction proceeded in a highly regioselective manner, i.e., the chlorine atom was introduced to the terminal position of the allene moiety while the lactone linkage was formed between the center carbon atom of the allene moiety and the hydroxyl oxygen, which was established by the X-ray single crystal diffraction study of γ-lactone 3p. The highly optically active 3-chloromethyl-2(5H)-furanones could be easily prepared from the readily available optically active 2,3-allenols. A mechanism for this reaction was proposed.

Allenyl ketones as versatile Michael acceptors for the addition of chelated enolates

Chelated amino acid ester enolates undergo clean 1,4-addition towards allenyl ketones 9, giving rise to unsaturated δ-keto amino acid esters 12 at low temperature. If the reaction is allowed to warm to room temperature, the enolate intermediates A undergo

Syntheses and synthetic applications of stannylated allylic alcohols

Allenyl carbinols undergo regioselective hydrostannation in the presence of MoBl3, a catalyst originally developed for the hydrostannation of alkynes, giving rise to allyl stannanes. These allyl stannanes can easily be converted into useful synthetic building blocks such as allyl iodides or vinyl epoxides.

A highly atom efficient, solvent promoted addition of tetraallylic, tetraallenic, and tetrapropargylic stannanes to carbonyl compounds

Tetraallylic, tetraallenic, and tetrapropargylic stannanes (0.25 equiv) react with aldehydes in methanol to provide unsaturated alcohols in good to excellent yields (56-99%). These reactions proceed exclusively with allylic rearrangement for tetra(2-butenyl)tin 2b and tetra(1,2-butadienyl)-tin 16c and predominantly with allylic rearrangement for tetrapropadienyltin 16a and tetra(2-butynyl)tin 6e. Allylation reactions also proceeded smoothly with reactive ketones such as ethyl pyruvate (9a) and cyclohexanone (9b). The corresponding TFA-catalyzed reactions of dimethyl acetals 4d and 4e are regiospecific with allylic rearrangement.