1720-32-7

Usage

Uses

1. Used in Membrane Studies:
1,6-Diphenyl-1,3,5-hexatriene is used as a fluorescence probe for membrane studies, specifically in the investigation of fluorescence depolarisation and membrane fluidity by flow cytometry. Its fluorescent properties allow researchers to gain insights into the structure and dynamics of biological membranes.
2. Used in Lipid Droplet Detection:
1,6-Diphenyl-1,3,5-hexatriene serves as an alternative to Nile red for the fluorescent detection of lipid droplets. This application is particularly useful in the study of lipid metabolism and storage, as well as in the development of new methods for detecting and analyzing lipid droplets in cells.

Synthesis Reference(s)

Synthesis, p. 731, 1990 DOI: 10.1055/s-1990-26998

Purification Methods

Crystallise the hexatriene from CHCl3 or EtOH/CHCl3 (1:1). [Beilstein 5 H 691, 5 IV 2425.]

InChI:InChI=1/C18H16/c1-2-3-6-15-18(16-11-7-4-8-12-16)17-13-9-5-10-14-17/h2-15H,1H2

Upstream product

• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 4403-20-7 1,6-diphenyl-hexa-1,5-diene-3,4-diol 
• 109-89-7 diethylamine 
• 100-42-5 styrene 
• 627-63-4 fumaryl dichloride 
• 591-50-4 iodobenzene 
• 2235-12-3 1,3,5-hexatriene 
• 6974-12-5 1,4-dibromo-2-butene 
• 100-52-7 benzaldehyde 
• 14371-10-9 (E)-3-phenylpropenal 
• 38633-40-8 (E)-cinnamyltriphenylphosphonium bromide 
• 104-55-2 3-phenyl-propenal 
• 170080-17-8 cis,cis,cis-1,6-diphenyl-1,3,5-hexatriene 
• 169887-08-5 di-(Z)-cinnamyl sulfone 

Downstream Products

• 38557-34-5 cis,trans,trans-1,6-Diphenyl-1,3,5-hexatriene 
• 1087-49-6 1,6-diphenylhexane 
• 1720-32-7 1,6-diphenylhexa-(1E,3Z,5E)-triene 
• 1610-23-7 1,6-dicyclohexylhexane 
• 205808-71-5 cis,cis,trans-1,6-diphenyl-1,3,5-hexatriene 
• 105230-99-7 1,4-dibenzyl-1,3-butadiene 
• 125341-43-7 C₁₈H₁₆^(1-)*C₁₆H₃₆N⁽¹⁺⁾ 
• 133786-85-3 (1R,2S,3S,4S,5S,6R)-1,6-Diphenyl-hexane-1,2,3,4,5,6-hexaol 
• 133786-85-3 (1R,2S,3R,4R,5S,6R)-1,6-Diphenyl-hexane-1,2,3,4,5,6-hexaol 
• 133786-85-3 (1S,2R,3R,4R,5S,6R)-1,6-Diphenyl-hexane-1,2,3,4,5,6-hexaol 
• 1720-32-7 all-trans-1,6-Diphenyl-1,3,5-hexatriene radical anion 
• 125341-49-3 C₁₈H₁₆^(1-)*Na⁽¹⁺⁾ 
• 1000689-24-6 [C₆H₅(CHCH)3C₆H₅((CH₃)5C₅)RuCl] 
• 17329-15-6 C₁₈H₁₆ 

Relevant academic research and scientific papers

Synthesis of diphenylhexatriene by the Pd-catalyzed dimerization of cinnamyl acetate

A mild and operationally simple method to synthesize diphenylhexatriene (DPH) is reported. The method relies on the Pd-catalyzed dimerization of cinnamyl acetate and provides efficient access to DPH in a single step.

Pd-Catalyzed Cross-Coupling of Organostibines with Styrenes to Give Unsymmetric (E)-Stilbenes and (1 E,3 E)-1,4-Diarylbuta-1,3-dienes and Fluorescence Properties of the Products

A general and effective palladium-catalyzed cross-coupling of organostibines with styrenes to give (E)-olefins was disclosed. By the use of an organostibine reagent, this method can produce unsymmetric (E)-1,2-diarylethylenes and (1E,3E)-1,4-diarylbuta-1,3-dienes in good yields with high E/Z selectivity and good functional group tolerance. Resveratrol and DMU-212 were synthesized in high yield. The protocol can be extended to the synthesis of (1E,3E,5E)-1,6-diphenylhexa-1,3,5-triene in 40% yield. Products 5e, 5f, and 7a showed good photoluminescence quantum yields ranging from 72 to 99%.

Palladium-Catalyzed Three-Component Reaction of 3-(Tri-n- butylstannyl)allyl Acetates, Aldehydes, and Triorganoboranes: An Alternative to the Carbonyl Allylation Using α,γ-Substituted Allylic Tin Reagents

A three-component reaction of 3-(tri-n-butylstannyl)allyl acetates, aldehydes, and triorganoboranes in the presence of a palladium-Xantphos catalyst system predominately gave (E)-anti-homoallylic alcohols with high diastereoselectivity and good to high levels of alkene stereocontrol. An efficient chirality transfer was observed when an enantioenriched substrate was employed. The reaction was initiated by the formation of an allylic gem-palladium/stannyl intermediate, which subsequently underwent allylation of the aldehyde by an allyltributyltin followed by a coupling reaction of the in-situ-generated (E)-vinylpalladium acetate with the triorganoborane.

Effect of substituents and conjugated chain length on the UV spectra of α,ω-di-substituted phenyl polyenes

A series of α,ω-di-substituted phenyl polyenes, p-X-Ph(CH = CH)nPh-p-Y (n = 1, 2, or 3) were synthesized, and their ultraviolet (UV) absorption maximum wavelength were determined. The correlation between molecular structure and the maximum wavelength energy (wavenumber/cm -1) was carried out. The results show that the maximum wavelength energy of the title compounds is mainly affected by both substituent excited-state parameters and maximum wavelength energy of the parent molecule. However, the two influence factors are not independent, and the action of substituent is governed by the parent molecular absorption energy. In the case of the compounds containing NO2 or NH2 groups, the influence of interaction of polarity parameters on the maximum wavelength energy must also be considered. In addition, the exploration was also made for the quantifying correlation of UV absorption maximum wavelength energy with the conjugated polarizability potential CPP replacing the parent molecular absorption energy. And the results indicate that the equation with CPP parameters is more accurate and convenient. Copyright 2013 John Wiley & Sons, Ltd. For the α,ω-di-substituted phenyl polyenes, p-X-Ph(CH = CH)nPh-p-Y (n = 1, 2, or 3), their ultraviolet absorption maximum wavelength energy (wavenumber/cm-1) was mainly affected by both substituent excited-state parameters and maximum wavelength energy of the parent molecule. However, the two influence factors are not independent, and the action of substituent is governed by the parent molecular absorption energy. Copyright

Z-selective metathesis homocoupling of 1,3-dienes by molybdenum and tungsten monoaryloxide pyrrolide (MAP) complexes

Molybdenum or tungsten monoaryloxide pyrrolide (MAP) complexes that contain OHIPT as the aryloxide (hexaisopropylterphenoxide) are effective catalysts for homocoupling of simple (E)-1,3-dienes to give (E,Z,E)-trienes in high yield and with high Z selectivities. A vinylalkylidene MAP species was shown to have the expected syn structure in an X-ray study. MAP catalysts that contain OHMT (hexamethylterphenoxide) are relatively inefficient.

Cyclopropanation of strained alkenes by palladium-catalyzed reaction of 3-trimethylsilyl- or 3-pinacolatoboryl-1-arylallyl acetates

The palladium-catalyzed cyclopropanation of strained alkenes with 3-trimethylsilyl- or 3-pinacolatoboryl-1-arylallyl acetate derivatives is described. This reaction gives cyclopropanation products in good to high yields with a single diastereomer, and the key step is likely to involve the formation of a palladacyclobutene complex from the α-trimethylsilyl- or α-pinacolatoboryl-σ-allylpalladium complex. Copyright

A highly tunable stereoselective olefination of semistabilized triphenylphosphonium ylides with N -Sulfonyl imines

The Wittig reaction involving direct olefination of triphenylphosphonium ylides (Ph3PCHR) with aldehydes is arguably the most often used method for alkene synthesis, but in general it yields mixtures of Z- and E-alkenes for semistabilized triphenylphosphonium ylides (R = aryl or vinyl). We have developed a simple and efficient protocol to improve the stereoselectivity significantly by replacing the aldehydes used in the Wittig reaction with N-sulfonyl imines, which possess distinct electronic and steric properties relative to aldehydes. A broad range of aromatic, α,β-unsaturated, and aliphatic imines bearing appropriate N-sulfonyl groups smoothly undergo olefination reaction with various benzylidenetriphenylphosphoranes or allylidenetriphenylphosphoranes under mild reaction conditions to afford an array of both Z- and E-isomers of conjugated alkenes in good to excellent yields and with greater than 99:1 stereoselectivity. Moreover, this tunable protocol has been successfully applied to the highly stereoselective synthesis of two anticancer agents, DMU-212 and its Z-isomer.

Photoisomerization of all-cis-1,6-diphenyl-1,3,5-hexatriene in the solid state and in solution: A simultaneous three-bond twist process

Disrotatory bicycle pedals: Irradiation of the title compound in the solid state gives the all-trans isomer directly in a crystal-to-crystal reaction. This threefold cis-trans photoisomerization is proposed to proceed by a two-stage mechanism that is consistent with two simultaneous bicyclepedal processes occurring in disrotatory fashion about the central bond.

A novel ambident reactivity of azolylacroleins

Reaction of azolylacroleins with phosphoranes bearing a conjugated double bond was found to yield either azolyltrienes in?a Wittig reaction, or to undergo cyclization to a dihydrobenzene containing the azole substituent. Transformation with an aza-Wittig reagent gave tetrazolylpyridines. The ambident reactivity was found to be dependent on the substituent of the phosphorane, which was rationalized by ab initio (DFT) calculation of the atomic charges of the reaction centres.

The effect of vicinyl olefinic halogens on cross-coupling reactions using Pd(0) catalysis

(trans) 1-Chloro-2-iodoethylene (3), (trans) 1-bromo-2-iodoethylene (4), (trans) 1,2-diiodoethylene (5) and (cis and trans) 1,2-dibromoethylene (11) were reacted under Suzuki, Sonogashira and Negishi cross-coupling conditions using Pd catalysis to obtain mono coupled products. Only olefin template 3 provided the desired coupling products reliably under all reaction conditions. Compound 5 did not provide cross coupled products under any of the reaction conditions used. The Negishi reaction was the only one that worked for templates 4 and 11. Studies indicate that oxidative addition of the most reactive carbon-halogen bond to Pd(0) is followed by elimination of the second halide, when the second halide is a bromide or an iodide. This happens to a much lesser degree when the second halogen is a chloride. Graphical Abstract.