143207-84-5

Upstream product

• 1100-88-5 benzyltriphenylphosphonium chloride 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 3892-92-0 (E)-3,4-dimethoxystilbene 
• 100-52-7 benzaldehyde 
• 100-39-0 benzyl bromide 
• 21852-32-4 4-bromomethyl-1,2-dimethoxybenzene 
• 36854-32-7 (E)-α-(3',4'-dimethoxyphenylmethylene)benzeneacetic acid 
• 14595-77-8 bis(trimethylsilyl)phenylmethane 
• 849590-35-8 N-(3,4-dimethoxybenzylidene)-2-methylpropane-2-sulfinamide 
• 1449-46-3 benzyltriphenylphosphonium bromide 

Downstream Products

• 3892-92-0 (E)-3,4-dimethoxystilbene 

Relevant academic research and scientific papers

Preparation of dihydroxy polycyclic aromatic hydrocarbons and activities of two dioxygenases in the phenanthrene degradative pathway

Dihydroxy phenanthrene, fluoranthene, and pyrene derivatives are intermediates in the bacterial catabolism of the corresponding parent polycyclic aromatic hydrocarbon (PAH). Ring-opening of the dihydroxy species followed by a series of enzyme-catalyzed re

Prevention of Marine Biofouling Using the Natural Allelopathic Compound Batatasin-III and Synthetic Analogues

The current study reports the first comprehensive evaluation of a class of allelopathic terrestrial natural products as antifoulants in a marine setting. To investigate the antifouling potential of the natural dihydrostilbene scaffold, a library of 22 syn

Z-Stereoselective Aza-Peterson Olefinations with Bis(trimethylsilane) Reagents and Sulfinyl Imines

Highly stereoselective aza-Peterson olefinations from bench-stable α,α-bis(trimethylsilyl)toluene reagents and N-substituted imines have been achieved using TMSO-/Bu4N+ as Lewis base activator in THF. Remarkably, and for the first time, N-t-butanesulfinyl imines were utilized for the synthesis of Z-stilbenes with excellent selectivities, while N-aryl imines generated E-stilbenes under identical reaction conditions. The protocol proved general for numerous examples with low molecular weight byproducts formed. The origin of the Z-selectivity is proposed to be a result of diastereoselective addition to N-t-butanesulfinyl imines followed by syn-elimination of an in situ formed hypervalent silicate.

Synthesis and biological evaluation of cytotoxic properties of stilbene-based resveratrol analogs

This work deals with the preparation of stilbene-based resveratrol analogs by employing the Perkin reaction, aiming at synthesizing potential antitumor lead compounds and evaluating their pharmacological activities. The proliferation inhibitor test against tumor cell lines identified analogs 9 and 11 as the most active among all synthesized derivatives, presenting IC50 in micromolar range for certain cell lines. For study on the embryonic development, compounds 8 and 9 at the lowest tested concentration (41.7 μM) that inhibited sea urchin egg development, but only after third cleavage were used. Both the compounds inhibited 100% of normal development since first cleavage. These data partially corroborated the results obtained with MTT assay using tumor cell lines. None of the tested compounds revealed hemolytic action in assay with mouse erythrocytes.

Methoxy-substituted stilbenes, styrenes, and 1-arylpropenes: Photophysical properties and photoadditions of alcohols

The photochemistry of trans-stilbene and four methoxy-substituted stilbene derivatives has been investigated in a variety of solvents. The fluorescence of all five trans isomers was quenched by 2,2,2-trifluoroethanol (TFE). Upon irradiation of the five substrates in TFE, the products derived from photoaddition of the solvent were detected. Nuclear magnetic resonance spectroscopy of the products formed by irradiation in TFE-OD indicated that the proton and nucleophile are attached to two adjacent atoms of the original alkene double bond. Irradiation of the corresponding methoxy-substituted styrenes and trans-1-arylpropenes in TFE produced the analogous solvent adducts. The photoaddition of TFE proceeded with the general order of reactivity: styre > trans-1-arylpropenes > trans-stilbenes. Transient carbocation intermediates were observed following laser flash photolysis of the stilbenes in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP). The results are consistent with a mechanism that involves photoprotonation of the substrates by TFE or HFIP, followed by nucleophilic trapping of short-lived carbocation intermediates. Compared to the other stilbene derivatives, trans-3,5-dimethoxystilbene displayed a large quantum yield of fluorescence and a low quantum yield of trans-cis isomerization in polar organic solvents. The unique photophysical properties of trans-3,5-dimethoxystilbene are attributed to formation of a highly polarized charge-transfer excited state (μe = 13.2 D).

The photochemical addition of 2,2,2-trifluoroethanol to methoxy-substituted stilbenes

The excited-state lifetime of the trans-stilbene chromophore in acetonitrile is prolonged by methoxy substituents in the meta positions. The long-lived singlet excited state of trans-3,5-dimethoxystilbene (trans-2d) is quenched upon the addition of 2,2,2-trifluoroethanol (TFE), and the Markovnikov ether is observed as the major product from steady-state irradiations. The results indicate that the reaction pathway proceeds through a carbocation intermediate.

A simple route to new phenanthro- and phenanthroid-fused thiazoles by a PIFA-mediated (hetero)biaryl coupling reaction

An application of the PIFA-mediated [PIFA: phenyliodine(III) bis(trifluoroacetate) biaryl coupling reaction is presented and extended to the formation of heterobiaryl connections. A preliminary study of the scope and limitations of this procedure was carried out in the synthesis of phenanthroids 11 from a series of phenethyl-substituted heterocycles 10, It was observed that in some cases a competitive dimerization process took place. It was also found that the coupling step could be efficiently extended to a larger number of examples if an aromatic ring were situated fused to the 1,2-diarylethane skeleton, as in 23 and 30. The synthesis of a series of 4,5-diarylthiazoles 23a-g was therefore carried out to explore the electronic requirements and the regioselectivity of the PIFA-mediated non-phenolic coupling reaction. When the same procedure was applied to aryl-heteroarylthiazoles 30, a series of phenanthroid-fused thiazoles 31 was obtained in good overall yields. To the best of our knowledge, no oxidative aryl-heteroaryl coupling reaction of this type had previously been reported. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Development of a polymer bound Wittig reaction and use in multi-step organic synthesis for the overall conversion of alcohols to β-hydroxyamines

An efficient combinatorial access to β-hydroxyamines suitable for automation is achieved by the mild oxidation of alcohols to aldehydes by polymer supported perruthenate (PSP), the subsequent clean olefination of the obtained aldehydes by polymer supported Wittig reagents followed by the epoxidation of the olefins by dimethyldioxirane (DMDO), and the final aminolysis of the epoxides with various amines is described.

Cis-trans isomerization and oxidation of radical cations of stilbene derivatives

Isomerization from cis stilbene derivatives (c-S (S = RCH=CHC6H5: 1, R = C6H5; 2, R = 4-CH3C6H4; 3, R = 4-CH3OC6H4 (= An); 4, R = 2,4-(CH3O)2C6H3; 5, R = 3,4-(CH3O)2C6H3; 6, R = 3,5-(CH3O)2C6H3; 7, AnCH=C(CH3)C6H5; 8, AnCH=CHAn)) to trans isomers (t-S) and oxidation of S with O2 were studied in γ-ray radiolyses of c-S in Ar-saturated 1,2-dichloroethane (DCE) and of S in O2-saturated DCE, respectively. On the basis of product analyses, it is suggested that a smaller barrier to c-t unimolecular isomerization for c-3.+-5.+ and 8.+ than for c-1.+, 2.+, and 6.+ due to the single bond character of the central C=C double bond for c-3.+-5.+ and 8.+ with a p-methoxyl group but not for c-l.+, 2.+, and 6.+ without a p-methoxyl group because of the contribution of a quinoid-type structure induced by charge-spin separation. The isomerization proceeds via chain reaction mechanisms involving c-t unimolecular isomerization and endergonic hole transfer or dimerization and decomposition. The isomerization of c-3.+ to t-3.+ is catalyzed by addition of 1,4-dimethoxybenzene but terminated by triethylamine. The regioselective formation of 3d in oxidation of 3.+ with O2 is explained by spin localization on the β-olefinic carbon in 3.+. The results of product analyses are compared with the rate constants of the unimolecular isomerization and the oxidation for S.+ measured with pulse radiolyses.