1794-46-3

Upstream product

• 58506-33-5 5-phenyl-trans,trans-2,4-pentadien-1-ol 
• 13466-40-5 (2E, 4E)-5-phenylpenta-2,4-dienal 
• 14371-10-9 (E)-3-phenylpropenal 
• 1826-67-1 vinyl magnesium bromide 
• 39806-16-1 ethyl (2E,4E)-5-phenyl-penta-2,4-dienoate 
• 100636-30-4 5-phenyl-2,4-pentadienoic acid chloride 
• 28010-12-0 5-phenylpenta-2,4-dienoic acid 
• 5208-89-9 (E)-1-phenyl-1,4-pentadien-3-ol 

Downstream Products

• 109529-99-9 diethyl <(2E,4E)-5-phenylpenta-2,4-dienyl>phosphonate 
• 444577-86-0 2-methyl-2-propenyl 5'-phenyl-(2'E,4'E)-pentadienyl sulfide 
• 1172595-19-5 phenyl((2E,4E)-5-phenylpenta-2,4-dienyl)sulfane 
• 1004960-59-1 (R,E)‐1‐phenylpenta‐1,4‐dien‐3‐ol 
• 105273-52-7 1-((E)-3-Phenyl-1-vinyl-allyl)-cyclohexanol 
• 134171-65-6 Trimethyl-{22-[4-((1E,3E,5E)-6-phenyl-hexa-1,3,5-trienyl)-phenyl]-docosyl}-ammonium; iodide 
• 134171-71-4 Dimethyl-{22-[4-((1E,3E,5E)-6-phenyl-hexa-1,3,5-trienyl)-phenyl]-docosyl}-amine 
• 128368-78-5 1-palmitoyl-2-(21-diphenylhexatrienyl-henicosanoyl)-sn-glycero-3-phosphocholine 
• 128368-81-0 21-[4-((1E,3E,5E)-6-Phenyl-hexa-1,3,5-trienyl)-phenyl]-henicosanoic acid methyl ester 
• 128368-79-6 21-[4-((1E,3E,5E)-6-Phenyl-hexa-1,3,5-trienyl)-phenyl]-henicosanoic acid 
• 444577-93-9 2-methyl-2-propenyl 5'-phenyl-(2'E,4'E)-pentadienyl sulfone 

Relevant academic research and scientific papers

Copper-Catalyzed Enantioselective Allylic Alkylation with a γ-Butyrolactone-Derived Silyl Ketene Acetal

Herein, we report a Cu-catalyzed enantioselective allylic alkylation using a γ-butyrolactone-derived silyl ketene acetal. Critical to the development of this work was the identification of a novel mono-picolinamide ligand with the appropriate steric and electronic properties to afford the desired products in high yield (up to 96 %) and high ee (up to 95 %). Aryl, aliphatic, and unsubstituted allylic chlorides bearing a broad range of functionality are well-tolerated. Spectroscopic studies reveal that a CuI species is likely the active catalyst, and DFT calculations suggest ligand sterics play an important role in determining Cu coordination and thus catalyst geometry.

Forging C-C Bonds with Hindered Nucleophiles and Carbonyl Electrophiles: Reactivity and Selectivity of Allylic Tin Reagents/n-BuLi

Under activation with n-BuLi, trialkylstannanes containing crotyl-, geranyl-, and phenyldienylmethyl appendages were reacted with efficiency and selectivity to various ketone and enone electrophiles with low reactivity. The straightforward process gives access to tertiary alcohols that are vicinal to quaternary carbons. With α,α′-dimethoxy-γ-pyrone, on the other hand, the grafting of a dienyl side chain was effected to prepare dienyl α′-methoxy-γ-pyrone in a stereo- and regioselective and convergent manner. Furthermore, the advantages of this route were highlighted for the preparation of organolithium species at low temperature with the formation of a minimum amount of salts. Synthetic manipulations were demonstrated to illustrate the potential of the chemistry for constructing acyclic and cyclic terpene scaffolds.

Allylic and allenic halide synthesis via NbCl5- and NbBr 5-mediated alkoxide rearrangements

(Chemical Equation Presented) Addition of NbCl5 or NbBr 5 to a series of magnesium, lithium, or potassium allylic or propargylic alkoxides directly provides allylic or allenic halides. Halogenation formally occurs through a metallahalo-[3,3] rearrangement, although concerted, ionic, and direct displacement mechanisms appear to operate competitively. Transposition of the olefin is equally effective for allylic alkoxides prepared by nucleophilic addition, deprotonation, or reduction. Experimentally, the niobium pentahalide halogenations are rapid, afford essentially pure (E)-allylic or -allenic halides after extraction, and are applicable to a range of aliphatic and aromatic alcohols, aldehydes, and ketones. 2009 American Chemical Society.

Stereoselective synthesis of substituted all-trans 1,3,5,7-octatetraenes by a modified Ramberg-B?cklund reaction

The reaction of allylic dienylic sulfone with dibromodifiuoromethane in the presence of alumina-supported KOH in dichloromethane solution results in facile rearrangement affording the corresponding all-trans 1,3,5,7-octatetraenes in excellent yields. This result shows that the double bonds of stereochemically defined allylic dienylic sulfone retain their stereochemistry and the newly formed double bond has an (E)-configurafion in the modified Rambeig-B?cklund procedure.

Novel Synthesis of Phenol Derivatives by Palladium-Catalyzed Cyclocarbonylation of 2,4-Pentadienyl Acetates

Phenyl acetates were selectively obtained in good yields by cyclocarbonylation of 2,4-pentadienyl acetates in the presence of NEt3, Ac2O, and a catalytic amount of palladium complexes such as PdCl2(PPh3)2 at 120-140 deg C under 50 atm of CO.No five-membered ring products were observed.A platinum complex PtCl2(PPh3)2 was also effective as a catalyst.The reaction of 5-phenyl-2,4-pentadienyl bromide with M(CO)(PPh3)3 (M = Pd or Pt) under CO gave the corresponding 6-phenyl-3,5-hexadienoyl complexes in a high yield, which in turn afforded 2-acetoxybiphenyl in 41-51percent yield on heating to 160 deg C under 50 atm of CO in the presence of NEt3 and Ac2O.Similar 3,5-hexadienoyl complexes are proposed to be intermediates in the catalytic cyclocarbonylation of 2,4-pentadienyl acetates.On the other hand, PdCl2(PPh3)2-catalyzed carbonylation of o-(bromomethyl)(1-alkenyl)benzenes in the presence of NEt3 and Ac2O gave 2-naphthyl acetates in moderate yields, while the reaction in the absence of Ac2O gave five-membered ring products such as 2-indanones or a tricyclic lactone by incorporation of one or two CO, respectively.

SYNTHESIS OF FLUORESCENT PROBES FOR LOCALIZED MEMBRANE FLUIDITY MEASUREMENTS

The synthesis of two long-chain homologues of the fluorescent membrane probes TMA-DPH and DPHpPC is described.The long-chain phosphatidylcholine could be synthesized from palmitoyl-lysophosphatidylcholine and 21-(diphenylhexatrienyl)henicosanoic acid only when the promoting agent was 1,1'-thionyldiimidazole.

1,1'-Thionyldi-imidazole in the synthesis of a long-chain phospholipidic membrane probe

A long-chain fluorescent membrane probe could be synthesized from palmitoyl-lysophosphatidylcholine and 21-(diphenylhexatrienyl)henicosanoic acid only when the promoting agent was 1,1'-thionyldi-imidazole.

Pyrazolopyrimidine Ribonucleosides as Anticoccidials. 3. Synthesis and Activity of Some Nucleosides of 4-pyrazolopyrimidines

Ribonucleosides of 4-(alkylthio)-1H-pyrazolopyrimidines have been shown to be useful anticoccidial agents .In that study, the unsaturated 4-allylthio and 4-crotylthio derivatives (19 and 20) were shown to be more active in vivo against Eimeria tenella than their saturated congeners; therefore, some unsaturated (arylalkyl)thio derivatives were synthesized and investigated as anticoccidial agents.The novel compounds in this study (2 to 18) were prepared by the alkylation of 4-mercapto-1-β-D-ribofuranosyl-1H-pyrazolopyrimidine (1), which was prepared by an enzymatic method.The (E)-4-cinnamylthio derivative (2) and the 5'-monophosphate (18) were the most active compounds against E. tenella in vivo.None of the analogues with substituents in the aryl moiety (3 to 13) was more active than 2 in vivo.The geometry about the double bond was important, since the (Z)-4-cinnamylthio derivative (14) was inactive both in vitro and in vivo.The 4-(3-phenylpropynyl)thio and 4-(5-phenyl-2,4-pentadienyl)thio derivatives (15 and 16) were at least as active as 2 in vitro; however, they were less active than 2 in vivo.Compound 2 was effective in vivo against E. tenella, E. necatrix, E. maxima, and E. brunetti; these species of Eimeria were controlled when 2 was given in the diet at levels up to 100 ppm.Infections in vivo due to E. acervulina were controlled by 2 only at about 800 ppm.The broad spectrum of anticoccidial activity shown by 2 represents a significant improvement over the activities reported for related compounds .