79144-14-2

Upstream product

• 100-52-7 benzaldehyde 
• 123-54-6 acetylacetone 
• 1235579-47-1 5,6-dimethyl-3-methylene-1-phenylhept-5-en-1-ol 

Downstream Products

• 58369-46-3 (E)-6-phenyl-5-hexene-2,4-dione 
• 1063666-87-4 C₁₅H₂₂O₃Si 
• 88083-79-8 6-methyl-2-phenyl-2,3-dihydro-4H-pyran-4-one 
• 1221016-29-0 1-hydroxy-1-phenyl-5-(trimethylsilyloxy)hex-4-en-3-one 

Relevant academic research and scientific papers

Chelation-control in the formal [3+3] cyclization of 1,3-bis-(silyloxy)-1,3-butadienes with 1-hydroxy-5-silyloxy-hex-4-en-3-ones. One-pot synthesis of 3-aryl-3,4-dihydroisocoumarins

The [3+3] cyclization of 1,3-bis(silyloxy)-1,3-butadienes with 1-hydroxy-5-silyloxy-hex-4-en-3-ones resulted in the one-pot formation of 3-aryl-3,4-dihydroisocoumarins. The reactions proceeded by regioselective cyclization to give 6-(2-aryl-2-chloroethyl)

Cyclization vs. elimination reactions of 5-Aryl-5-hydroxy 1,3-diones: One-pot synthesis of 2-Aryl-2,3-dihydro-4H-pyran-4-ones

2-Aryl-2,3-dihydro-4H-pyran-4-ones were prepared in one step by cyclocondensation of 1,3-diketone dianions with aldehydes. The use of HCl (10%) for the aqueous workup proved to be very important to avoid elimination reactions of the 5-aryl-5-hydroxy 1,3-d

Cobalt-catalyzed 1,4-hydrovinylation of allylsilane and allylboronic esters for the synthesis of hydroxy-functionalized 1,4-dienes

(Figure presented) The cobalt(I)-catalyzed 1,4-hydrovinylation reaction of allyl trimethylsilane and allyl pinacol boronic ester with symmetrical and unsymmetrical 1,3-dienes generates building blocks for the in situ allylboration or the Lewis acid induced allylation reaction utilizing the corresponding allyl silane derivatives. The products of these three-component reactions are hydroxy-functionalized 1,4-dienes which can be used for the synthesis of pyranones. An alternate reaction sequence for the synthesis of the hydroxy-functionalized 1,4-dienes by performing the allylation first followed by the cobalt-catalyzed 1,4-hydrovinylation is also possible. Accordingly, polyfunctionalized complex structures can be generated by both approaches in a convergent fashion.

One-pot synthesis of 6-aryl-2,3-dihydro-4H-pyran-4-ones by cyclocondensation of 1,3-diketone dianions with aldehydes

6-Aryl-2,3-dihydro-4H-pyran-4-ones were prepared in one step by cyclocondensation of 1,3-diketone dianions with aldehydes. The use of hydrochloric acid (10%) for the aqueous work-up proved to be very important.

Synthesis of 3-aryl-3,4-dihydroisocoumarins by regioselective domino '[3+3] cyclization/lactonization' reactions of 1,3-bis-(silyloxy)-1,3-butadienes with 1-hydroxy-5-silyloxy-4-en-3-ones

The [3+3] cyclization of 1,3-bis(silyloxy)-1,3-butadienes with 1-hydroxy-5-silyloxy-4-en-3-ones afforded 6-(2-aryl-2-chloroethyl)salicylates, which were transformed into 3-aryl-3,4-dihydroisocoumarins by silica gel-mediated lactonization.

Organic syntheses via transition metal complexes, LXXXVIII: 1-Metalla-1,3,5,7-octatetraenes from (1-alkynyl) carbene complexes of chromium and tungsten via [6-(1-alkenyl)]pyranylidene complexes

[6-(1-Ethenyl)]pyran-2-ylidene complexes 4a,b and [6-(1-butadienyl)]pyran-2-ylidene complexes 6a,b are obtained as major products together with the corresponding regioisomeric pyranylidene complexes 5a,b and 7a,b respectively as minor products by base-induced condensation of (1-alkynyl)carbene complexes (CO)5M=C(OEt)-C≡CPh 1a,b (M = Cr, W) with trans-6-phenyl-5-hexene-2,4-dione (2b) and trans,trans-8-phenyl-octa-5,7-diene-2,4-dione (2c) in moderate yields. X-ray data of the isomeric tungsten complexes 4b and 5b [C26H16O7W, blue (red), triclinic (monoclinic), space group P1 (P21/c), Z = 2 (4)] and the pyranylidene compound 6b [C28H18O7W, triclinic, space group P1, Z = 2] are reported. Amination of compound 4b with dimethylamine affords 1-metalla-1,3,5,7-octatetraenes (Z,Z,E)-9A and (Z,Z,E)-9B (2:1) in 89% total yield.

EFFICACIOUS ENTRY INTO SUBSTITUTED 5,6-DIHYDRO-4-HYDROXY-2H-PYRAN-2-ONES AND 2,3-DIHYDRO-4H-PYRAN-4-ONES UTILIZING KETONIC DIANIONS

Methyl acetoacetate and 2,4-pentanedione dianions were condensed with aldehydes and ketones to afford a 1,3,5-trioxygenated carboskeleton.Intramolecular cyclization of the aldol adducts delivered the title compounds in good yield.