4403-20-7

Usage

Uses

Used in Pharmaceutical Industry:
1,6-Diphenyl-1,5-hexadiene-3,4-diol is used as a pharmaceutical agent for its potential health benefits, including its antioxidant and anti-inflammatory properties. It is being studied for its potential to prevent and treat various diseases, such as cancer, diabetes, and cardiovascular diseases.
Used in Cosmetic and Skincare Industry:
1,6-Diphenyl-1,5-hexadiene-3,4-diol is used as an antioxidant in cosmetic and skincare products to protect the skin from oxidative stress and promote overall skin health. Its anti-inflammatory properties may also help reduce skin inflammation and improve skin appearance.

InChI:InChI=1/C18H18O2/c19-17(13-11-15-7-3-1-4-8-15)18(20)14-12-16-9-5-2-6-10-16/h1-14,17-20H

Upstream product

• 37973-54-9 1,1-diacetoxy-3-phenylprop-2-ene 
• 104-55-2 3-phenyl-propenal 
• 64-17-5 ethanol 
• 14371-10-9 (E)-3-phenylpropenal 
• 859974-72-4 3,4-bis-benzoyloxy-1,6-diphenyl-hexa-1,5-diene 

Downstream Products

• 1720-32-7 1,6-diphenyl-hexa-1,3,5-triene 
• 15962-89-7 1,6-diphenyl-hexane-3,4-diol 
• 104-55-2 3-phenyl-propenal 
• 105230-99-7 1,4-dibenzyl-1,3-butadiene 
• 1610-23-7 1,6-dicyclohexylhexane 
• 1087-49-6 1,6-diphenylhexane 
• 621-82-9 Cinnamic acid 
• 57586-19-3 C₃₀H₄₆O₂Si₂ 

Relevant academic research and scientific papers

In/InCl3-mediated cross-coupling reactions of methyl vinyl ketone with benzaldehyde in aqueous media

(matrix presented) Various β,γ-unsaturated ketones were successfully prepared by cross-coupling reactions of methyl vinyl ketone (MVK) with benzaldehydes mediated by In/InCl3 in aqueous media.

Selective Pinacol-Coupling Reaction using a Continuous Flow System

The first continuous flow pinacol coupling reaction of carbonyl compounds was successfully achieved within only 2 min during a single pass through a cartridge filled with zinc(0). The optimized method allowed the efficient production of gram-scale value-added compounds with high productivity. The developed methodology is efficient for aromatic or α,β-unsaturated aldehydes but gives moderate results for more stable acetophenone derivatives. Moreover, the flow method displayed better results in terms of yield and selectivity in comparison to the corresponding batch methodology.

First pinacol coupling in emulsified water: Key role of surfactant and impact of alternative activation technologies

For the first time, the influence of surfactants on the radical pinacol coupling reaction is investigated. The rate and selectivity of this reductive C-C coupling are compared under three different activation technologies: thermal activation, microwave irradiation, and sonication. The use of IgepalCO520, a neutral surfactant, led to the successful conversion of aromatic or α,β-unsaturated aliphatic carbonyl compounds in moderate to excellent yield (55-90 %). An insight on the potential mechanism involved in the reaction is also proposed, based on microscopic observations and particle size measurement.

Selective Pinacol Coupling on Regeneratable Supported Acids in Sole Water

Efficient pinacol coupling was developed in sole water, using a reusable heterogeneous supported acid source and zinc as cheap available metal source. This medium can be easily regenerated up to 10-fold without loss of activity. Moreover, supported acids enhance the selectivity of the pinacol coupling reaction compared with homogeneous acids.

Mg/Triethylammonium formate: A useful system for reductive dimerization of araldehydes into pinacols; Nitroarenes into azoarenes and azoarenes into hydrazoarenes

Studies are reported which describes the effectiveness of triethylammonium formate in the presence of magnesium for the efficient intermolecular pinacol coupling using MeOH as solvent, Various aromatic carbonyls underwent smooth reductive coupling to give the corresponding I ,2-diols. A series of azo compounds were obtained by the reductive coupling of nitroaromatics while azo compounds were reduced to the corresponding hydrazoarenes by this system. There was no adverse effect on the other reducible and hydrogenolysable groups such as ether linkage, hydroxy and halogens. The reactions are clean, high yielding and inexpensive. All the reactions proceeded smoothly at ambient temperature.

A new Yb3+-catalyzed pinacol and imine-coupling reaction

Ytterbium triflate, Yb(OTf)3, catalyzes the intermolecular reductive homocouplings of imines, aldehydes, and ketones at loadings of 5 mol % in the presence of Mg and Me3SiCl to give isolated yields of up to 95%. Diastereoselectivity of up to 4/96 (dl/meso) is achieved for aromatic aldehydes, up to 100% dl for aliphatic aldehydes, and 100% dl for an intramolecular imine coupling.

Pinacol coupling reaction of aromatic aldehydes mediated by aqueous vanadium(II) solution under ultrasound irradiation

Pinacol coupling of aromatic aldehydes by aqueous vanadium(II) solution under ultrasound irradiation at room temperature can lead to the corresponding pinacols in 54-93% yields within 15-30 min. Copyright Taylor & Francis, Inc.

Pinacol coupling reaction of beta-halo-alpha,beta-unsaturated aldehydes promoted by TiI4.

The pinacol reaction of beta-halogenated alpha,beta-unsaturated aldehydes was promoted by titanium tetraiodide to give coupling products in good yields with high dl-selectivity. Subsequent reduction with H(2)/Pd-C gave saturated vic-diols in good yields. Heck coupling reaction enabled the displacement of halogens with vinyl groups without the loss of stereochemical integrities. [reaction: see text]

Pinacol coupling of aromatic aldehydes and ketones using Zn-ZnCl2 under ultrasound

The coupling reaction of aromatic aldehydes and ketones leading to pinacols has been carried out using Zn-ZnCl2 in 50% aq. THF under ultrasound in 5-77% yield.

Pinacol coupling of aromatic aldehydes and ketones using magnesium in aqueous ammonium chloride under ultrasound

The pinacol coupling reaction of aromatic aldehydes and ketones was performed in 8-95% yield with magnesium in 0.1 M aqueous NH4C1 under ultrasound irradiation at r.t. for 3 h.