17733-79-8

Upstream product

• 3041-57-4 1-Phenyl-4-hydroxy-5-chlorpentin-⁽¹⁾ 
• 3305-63-3 2-(3-phenyl-2-propynyl)ethylene oxide 
• 107-19-7 propargyl alcohol 
• 536-74-3 phenylacetylene 
• 41769-31-7 methyl 5-phenylpent-2-en-4-ynoate 
• 1004-22-4 (phenylethynyl)sodium 
• 106-89-8 epichlorohydrin 
• 198693-62-8 tert-Butyl-dimethyl-((E)-5-phenyl-pent-2-en-4-ynyloxy)-silane 
• 117552-48-4 E-5-phenyl-pent-2-en-4-ynoic acid ethyl ester 
• 13633-26-6 4-phenylbut-1-en-3-yne 
• 53326-58-2 cis-1,4-bis(trimethylsilyloxy)-2-butene 
• 30353-46-9 5-phenyl-2,4-pentadiyn-1-ol 
• 27948-27-2 (E)-methyl 5-phenylpent-2-en-4-ynoate 
• 1504-58-1 3-Phenyl-2-propyn-1-ol 

Downstream Products

• 99851-76-0 (5-bromopent-3-en-1-yn-1-yl)benzene 
• 64907-51-3 (E)-(5-chloropent-3-en-1-yn-1-yl)benzene 
• 30625-91-3 (E)-5-phenylpent-2-en-4-ynal 
• 287471-31-2 (E)-(5-bromopent-3-en-1-yn-1-yl)benzene 
• 1424055-74-2 C₁₂H₁₁NO₃ 
• 351863-99-5 (E)-(S)-2-ethoxy-3-[4-(5-phenyl-pent-2-en-4-ynyloxy)-phenyl]-propionic acid ethyl ester 

Relevant academic research and scientific papers

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.

A highly practical approach to chiral homoallylic-homopropargylic amines via aza-Barbier reaction

The first access to chiral homoallylic-homopropargylic amine bearing two contiguous stereocenters has been well accomplished via zinc-promoted aza-Barbier reaction. N-tert-Butanesulfinyl ketimines are well-tolerated substrates, providing the tertiary amin

Rhodium-catalyzed chemo- and regioselective cross-dimerization of two terminal alkynes

Cross-dimerization of terminal arylacetylenes and terminal propargylic alcohols/amides has been achieved in the presence of a rhodium catalyst. This method features high chemo- and regioselectivities rendering convenient and atom economical access to functionalized enynes.

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.

Process development and scale-up of the PPAR agonist NNC 61-4655

A scalable synthetic route of the nonselective but PPARα-preferring potent PPAR agonist NNC 61-4655 aimed for treatment of type 2 diabetes was developed. The synthetic pathway comprises the convergent synthesis and coupling of the two key intermediates E-5-(chloropent-3-en-1-ynyl)benzene 8 (prepared in a five-step synthesis in 18% overall yield) and (S)-2-ethoxy-3-(4- hydroxyphenyl)propanoic acid isopropyl ester 9. The 2-aminoethanol salt of NNC 61-4655 was selected in a preclinical salt selection program as the appropriate salt form for further development. More than 900 g of NNC 61-4655, 2-aminoethanol was finally synthesized under GMP in 98.7% purity. In comparison to the original medicinal chemistry route, starting from phenylpropargyl aldehyde 1, the overall yield towards NNC 61-4655 could be enhanced from 24 to 37%. An improved scalable two-step synthesis for 8 was developed on a laboratory scale (≥33-35% overall yield) shortly after the GMP batch.

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