14604-31-0

Upstream product

• 104-55-2 3-phenyl-propenal 
• 74-86-2 acetylene 
• 14371-10-9 (E)-3-phenylpropenal 
• 1133296-08-8 C₁₄H₁₈OSi 
• 65032-27-1 ethynylmagnesium chloride 
• 75-24-1 trimethylaluminum 
• 1066-26-8 sodium acetylide 
• 4301-14-8 acetylenemagnesium bromide 
• 108-05-4 vinyl acetate 
• 14604-31-0 (E)-1-phenylpent-1-en-4-yn-3-ol 
• 155931-09-2 C₁₄H₁₈OSi 
• 70277-75-7 lithium acetylide 
• 1066-54-2 trimethylsilylacetylene 
• 501072-27-1 (E)-3-hydroxy-1-phenyl-5-trimethylsilyl-1-penten-4-yne 

Downstream Products

• 14604-31-0 (1E,3S)-1-phenylpent-1-en-4-yn-3-ol 
• 63399-81-5 Acetic acid (E)-(R)-1-ethynyl-3-phenyl-allyl ester 
• 129571-75-1 Acetic acid (E)-(S)-1-ethynyl-3-phenyl-allyl ester 
• 193685-91-5 (E)-1-phenylpent-1-en-4-yn-3-yl acetate 
• 905946-13-6 (E)-3-hydroxy-5-phenyl-1-(2-thienyl)-4-penten-1-yne 
• 1133296-08-8 C₁₄H₁₈OSi 
• 1338443-10-9 (1E,4E)-1-(dimethyl(phenyl)silyl)-5-phenylpenta-1,4-dien-3-ol 
• 14164-31-9 (2E,4E)-5-phenylpenta-2,4-dicarbonitrile 
• 14164-31-9 (Z)-(4E)-5-phenylpenta-2,4-dienenitrile 

Relevant academic research and scientific papers

Ene-Yne Metathesis of Allylphosphonates and Allylphosphates: Synthesis of Phosphorus-Containing 1,3-Dienes

A variety of ene-yne cross metathesis reactions were performed using unsaturated phosphonate and phosphate reagents, affording the corresponding phosphorylated 1,3-diene products in good to excellent yields. These difficult ene-yne metatheses employed a Grubbs catalyst bearing a cyclic amino alkyl carbene ligand. A variety of terminal alkynes of varying substitution underwent the reaction, and different phosphorus-containing alkenes were found to give the conjugated diene products in high yields. The resulting dienes were further transformed by Horner-type Wittig reactions and a Diels-Alder cycloaddition.

A bifunctional ligand enables efficient gold-catalyzed hydroarylation of terminal unactivated propargylic alcohols with heteroareneboronic acids

Terminal allylic alcohols are important motifs in natural products, and also key intermediates/precursors in numerous novel reaction transformations. In this study, enabled by a bifunctional ligand featuring a basic amino group, a gold-catalyzed hydroarylation of terminal unactivated propargylic alcohols with heteroareneboronic acids has been first established, and efficiently affords various terminal aryl-substituted allylic alcohols with moderate to high yields under mild conditions.

Tertiary enamide-promoted diastereoselective domino: N-acyliminium ion trapping and nazarov cyclization

N-Acyliminium ions generated from enamidyl vinyl ketones provided cyclopentenoid-fused diazepines diastereoselectively using BF3·Et2O in one pot through a domino N-acyliminium ion trapping/Nazarov reaction, simultaneously generating three new stereogenic centers. The particular structural design of the cross-conjugated dienone dictates the torquoselectivity observed in this polarized Nazarov reaction. Various N-bridgehead polycyclic scaffolds of putative pharmacological interest were obtained. Cyclic voltammetry was used to support the preferred reaction sequence within this domino reaction.

Coupling-Isomerization-Cycloisomerization Reaction (CICIR) – An Unexpected and Efficient Domino Approach to Luminescent 2-(Hydroxymethylene)indenones

A Pd/Cu-catalyzed base mediated domino process of ortho-halo (hetero)aryl carboxaldehydes and propargyl alcohols unexpectedly furnish 2-(hydroxymethylene)indenones in good to excellent yield as a result of a coupling-isomerization-cycloisomerization reaction (CICIR). In addition, the title compounds constitute an interesting class of luminophores with tunable emission solvatochromicity.

Metal-free synthesis of activated ynesulfonamides and tertiary enesulfonamides

An operationally simple synthesis of activated ynesulfonamides and enesulfonamides is described. Ynesulfonamides can be obtained through reaction of sulfonylamides with activated bromoalkynes and Triton B in a short time at room temperature. Likewise, terminal alkynes react with sulfonylamides to provide enesulfonamides. Z/E enesulfonamides can be transformed exclusively into E enesulfonamides.

Trialkylborane-Mediated Multicomponent Reaction for the Diastereoselective Synthesis of Anti-δ,δ-Disubstituted Homoallylic Alcohols

The trialkylborane/O2-mediated reaction of propargyl acetates having a tributylstannyl group at an alkyne terminus with aldehydes in a THF-H2O solvent system gave anti-δ,δ-disubstituted homoallylic alcohols with good to high diastereoselectivity. Intriguingly, two alkyl groups derived from trialkylborane were embedded into the reaction product. The trialkylborane plays a key role not only as a radical initiator but also as a source of alkyl radicals.

Allenylic Carbonates in Enantioselective Iridium-Catalyzed Alkylations

An enantioconvergent C(sp3)-C(sp3) coupling between racemic allenylic electrophiles and alkylzinc reagents has been developed. An Ir/(phosphoramidite,olefin) catalyst provides access to highly enantioenriched allenylic substitution p

Ligand-Effect in Gold(I)-Catalyzed Rautenstrauch Rearrangement: Regio- and Stereoselective Synthesis of Bicyclo[3.2.1]octa-3,6-dienes through Cyclodimerization of 1-Ethynyl-2-propenyl Esters

Gold(I) complexes bearing sterically demanding phosphine ligands such as tBuXphos catalyze the cascade Rautenstrauch rearrangement/[4 + 3] cycloaddition of 1-ethynyl-2-propenyl esters. The reaction provides an efficient and straightforward rout

Rhodium-catalyzed synthesis of 1,2-dihydropyridine by a tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole

A tandem reaction of 4-(1-acetoxyallyl)-1-sulfonyl-1,2,3-triazole including formation of α-imino rhodium carbene, 1,2-migration of an acetoxy group and six electron electrocyclic ring closure was reported. The migration of the OAc group with excellent chemoselectivity was the crucial process, leading to the formation of 1,2-dihydropyridine specifically in up to 90% yield. Several transformations of the dihydropyridine product were also achieved illustrating the potential of the protocol in organic synthesis. Based on the observation of the intermediate, a plausible mechanism was proposed.

Cu-Pybox catalyzed synthesis of 2,3-disubstituted imidazo[1,2-a]pyridines from 2-aminopyridines and propargyl alcohol derivatives

A highly efficient cascade sequence for syntheses of 2,3-disubstituted imidazo[1,2-a]pyridines with exclusive regioselectivity in moderate to excellent yields has been developed. This cascade was initiated through propargylation of 2-aminopyridines at pyridine-nitrogen with propargyl alcohol derivatives using Cu(II)-Pybox as catalyst and followed by an intramolecular cyclization and isomerization. Besides 2-aminopyridine, less reactive 2-aminopyrimidine, 2-aminopyrazine and 3-aminopyridazine were also suitable in this cascade.