129593-48-2

Upstream product

• 1004-22-4 (phenylethynyl)sodium 
• 106-89-8 epichlorohydrin 
• 117552-48-4 E-5-phenyl-pent-2-en-4-ynoic acid ethyl ester 
• 536-74-3 phenylacetylene 
• 107-19-7 propargyl alcohol 
• 27948-27-2 (E)-methyl 5-phenylpent-2-en-4-ynoate 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 
• 24595-58-2 5-phenylpent-4-yn-1-ol 
• 27948-26-1 (Z)-methyl 5-phenylpent-2-en-4-ynoate 
• 185841-11-6 (Z)-3-(butyltellanyl)prop-2-en-1-ol 
• 729593-95-7 (-)-(S)-2-(Z)-4-(Z)-5-phenyl-4-(p-tolylsulfinyl)penta-2,4-dien-1-ol 
• 13633-26-6 4-phenylbut-1-en-3-yne 
• 53326-58-2 cis-1,4-bis(trimethylsilyloxy)-2-butene 
• 189368-12-5 (Z)-5-phenyl 2-penten-4-ynoic acid ethyl ester 

Downstream Products

• 64907-51-3 (E)-(5-chloropent-3-en-1-yn-1-yl)benzene 
• 30625-91-3 (E)-5-phenylpent-2-en-4-ynal 
• 351863-99-5 (E)-(S)-2-ethoxy-3-[4-(5-phenyl-pent-2-en-4-ynyloxy)-phenyl]-propionic acid ethyl ester 
• 24595-58-2 5-phenylpent-4-yn-1-ol 
• 568571-28-8 2-bromo-1-[(Z)-5-phenylpent-2-en-4-ynyl]-1H-indole-3-carboxaldehyde 
• 568571-18-6 (Z)-(5-bromopent-3-en-1-yn-1-yl)benzene 
• 129593-52-8 (Z)-1-(tert-Butyl-dimethyl-silanyloxy)-8-phenyl-oct-5-ene-2,7-diyn-4-ol 
• 129593-61-9 (Z)-2-(Diphenyl-phosphinoyl)-8-phenyl-octa-2,3,5-trien-7-yn-1-ol 
• 129618-64-0 tert-Butyl-[(Z)-2-(diphenyl-phosphinoyl)-8-phenyl-octa-2,3,5-trien-7-ynyloxy]-dimethyl-silane 
• 2689-59-0 (furan-2-yl)(phenyl)methanone 

Relevant academic research and scientific papers

Conjugated enynes as a new type of substrates for olefin metathesis

(Matrix presented) It has been demonstrated for the first time that conjugated enynes can be employed as a facile substrate in olefin metathesis with the use of a bispyridine-substituted ruthenium benzylidene catalyst. Cross-metathesis of the enynes with

Chemoselective Biohydrogenation of Alkenes in the Presence of Alkynes for the Homologation of 2-Alkynals/3-Alkyn-2-ones into 4-Alkynals/Alkynols

The chemoselective hydrogenation of alkenes in the presence of alkynes is a very challenging transformation to achieve with traditional chemical methods. The development of an effective procedure to perform this transformation would enrich the tool-kit available to organic chemists for the development of useful synthetic routes, and the creation of novel structural motifs. The reduction of activated alkene bonds by ene-reductases (ERs) is completely chemoselective, because of the mechanism of the reaction. Thus, we investigated the use of ERs belonging to the Old Yellow Enzyme family for the reduction of α,β-unsaturated aldehydes with a conjugated C≡C triple bond at the γ position. This reaction was exploited as the key step for the development of an effective homologation route to convert aryl and alkyl substituted propynals and butynones into 4-alkynals and 4-alkynols, avoiding some troublesome or hazardous steps of known synthetic routes. (Figure presented.).

Method for synthesizing trans-2-alkene-4-alkyne-1-alcohol compound

The invention discloses a method for synthesizing a trans-2-alkene-4-alkyne-1-alcohol compound. The method comprises the following steps: by taking 2-propinyl ethylene oxide of a formula I shown in the specification as an initiator, heating the initiator to 80-100 DEG C to implement a reaction over night in the presence of a gold catalyst, tert(3,5-di(trifluoromethyl) phenyl) sodium borate and a solvent so as to obtain a reaction liquid, and performing separation and purification on the reaction liquid so as to obtain a trans-linear 2-alkene-4-alkene-1-alcohol compound of a formula II shown inthe specification, wherein the mass ratio of the tert(3,5-di(trifluoromethyl) phenyl) sodium borate to the gold catalyst to the 2-propinyl ethylene oxide of the formula I is (0.05-0.1):(0.02-0.05):1. The raw materials and the reaction process of the method are safe and environment-friendly, and the product is single in structure, good in selectivity and free of isomer; the raw materials are easyto obtain, the configuration of the raw material is not specially required, the reaction steps are simple, and the method is a novel way for synthesizing the trans-2-alkene-4-alkyne-1-alcohol compound.

Stereoselective Traceless Borylation–Allenation of Propargylic Epoxides: Dual Role of the Copper Catalyst

Chiral α-allenols are prepared with high diastereocontrol through an unprecedented and spontaneous β-oxygen elimination of an α-epoxy vinyl boronate. Stochiometric experiments and DFT calculations support a dual role of the copper catalyst, which orchestrates the hydroboration and the syn-elimination step.

E-Selective dimerization of phenylacetylene catalyzed by cationic tris(μ-hydroxo)diruthenium(II) complex and the mechanistic insight: The role of two ruthenium centers in catalysis

A dinuclear complex [(Me3P)3Ru(μ-OH)3Ru(PMe3)3]+[OPh]? (1) (0.5 mol%) catalyzes E-selective dimerization of phenylacetylene, which involves the C–H bond cleavage of phenylacetyle

A Trialkylphosphine-Derived Palladacycle as a Catalyst in the Selective Cross-Dimerization of Terminal Arylacetylenes with Terminal Propargyl Alcohols and Amides

A method for the selective cross-dimerization of terminal aryl alkynes with propargyl alcohols to afford linear (E)-enynol products is reported. The complex [Pd(μ-κ2-O,O-OAc)(κ2-C,P-(t-Bu)2PCH2C(Me)2CH2)]2 selectively affords (E)-5-aryl-2-en-4-yn-1-ol products in good yields under mild conditions with high chemo-, regio-, and stereoselectivity. In contrast, previously reported examples of this reaction afford the branched 4-aryl-2-hydroxymethanol-1-buten-3-yne. Propargyl amides are also selectively cross-dimerized, but with lower regioselectivity for the linear enyne. The method has been applied to the synthesis of (E)-5-phenyl-2-penten-4-yn-1ol, which is a precursor to type 2 diabetes drug candidate NNC 61-4655, in 72% yield from phenylacetylene and propargyl alcohol. The palladacycle precatalyst reacts with aryl alkynes to afford the first example of a dimeric palladacycle complex with a μ-κ2-C1,C1-bound acetylide ligand. This complex is observed during the catalytic reaction and is a competent precatalyst.

Metal-catalyzed formation of 1,3-cyclohexadienes: A catalyst-dependent reaction

A metal-dependent and complementary catalytic method to synthesize the cyclohexadienes has been developed. When gold or indium salts were used as catalysts, 1,3-cyclohexadiene (1,3-CHD) could be obtained; when Cu(OTf)2 was used as the catalyst,

Sulfur-directed enantioselective synthesis of functionalized dihydropyrans

(Chemical Equation Presented) The highly selective base-promoted cyclization of enantiopure sulfinyl dienols affords allylic sulfinyl dihydropyrans. The scope of this methodology, including the preparation of seven-membered rings, has been studied in dept

Regioselective cis,vic-dihydroxylation of α,β,γ,δ- unsaturated carboxylic esters: Enhanced γ,δ-selectivity by employing trifluoroethyl or hexafluoroisopropyl esters

The regioselectivity of Sharpless asymmetric dihydroxylation (AD) of α,β,γ,δ-unsaturated carboxylic esters was studied as a function of α-, β-, and δ-substituents and for fluorine-free versus fluorinated esters. The latter showed increased or complete γ,δ-selectivities: the hexafluoroisopropyl ester being superior to the trifluoroethyl ester. Olefinations of α,β-unsaturated aldehydes with phosphorus ylide 36 or phosphonate anion 41 provided α,β, γ,δ-unsaturated trifluoroethyl esters, leading inter alia to complete trans selectivity and to 31 with 94% E selectivity, respectively. Georg Thieme Verlag Stuttgart.

Synthesis of 1,3-enynes via Suzuki-type reaction of vinylic tellurides and potassium alkynyltrifluoroborate salts

The palladium-catalyzed cross-coupling reaction between potassium alkynyltrifluoroborate salts and vinylic tellurides proceeds readily to afford 1,3-enynes with moderate to good yields.