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Upstream product

• 101-84-8 diphenylether 
• 37592-19-1 3-allyloxyanisole 
• 10016-20-3 alpha cyclodextrin 
• 5446-02-6 4-methoxymethylsalicylate 
• 108-46-3 recorcinol 
• 133730-24-2 1-Bromo-4-methoxy-2-(methoxymethoxy)benzene 
• 63604-94-4 2-bromo-5-methoxyphenol 
• 150-19-6 O-methylresorcine 
• 7585-39-9 β‐cyclodextrin 
• 107-05-1 3-chloroprop-1-ene 
• 668455-70-7 2-(allyloxy)-4-methoxybenzoic acid 
• 121-69-7 N,N-dimethyl-aniline 
• 2237-36-7 4-methoxysalicylic acid 
• 31456-95-8 Methyl 4-methoxy-2-(prop-2-enyloxy)benzoate 

Downstream Products

• 91-52-1 2,4 dimethoxybenzoic acid 
• 3698-23-5 Osmorhizole 
• 140660-39-5 3-(4-cyanobutoxy)-4-allylanisole 
• 83394-21-2 ethyl 5-(2-allyl-5-methoxyphenoxy)-1-benzyl-v-triazole-4-carboxylate 
• 150-19-6 O-methylresorcine 
• 53596-61-5 6-methoxy-2-methyl-2,3-dihydrobenzofuran 
• 6738-38-1 2-allyl-3-methoxyphenol 
• 140660-40-8 3-(4-cyanobutoxy)-4-propylanisole 
• 117706-04-4 5-[5-Hydroxy-4-(1-oxopropyl)-2-allylphenoxy]pentanenitrile 
• 117690-91-2 5-(2-Allyl-4-propanoyl-5-methoxyphenoxy)pentanenitrile 
• 117706-03-3 4-(4-cyanobutoxy)-5-allyl-2-hydroxybenzophenone 
• 117690-92-3 4-(4-cyanobutoxy)-5-allyl-2-methoxybenzophenone 
• 117706-06-6 5-[5-Hydroxy-4-(1-oxodecyl)-2-allylphenoxy]pentanenitrile 
• 205433-74-5 2-allyl-1-(benzyloxy)-4-methoxybenzene 

Relevant academic research and scientific papers

Using geminal dicationic ionic liquids as solvents for high-temperature organic reactions

(Chemical Equation Presented) Several organic reactions conducted at high temperatures, including the isomerization reaction, the Claisen rearrangement, and the Diels-Alder reaction, were investigated in three geminal dicationic ionic liquids with high thermal stability. High to moderate yields of the products for most entries were obtained. Advantages of these approaches are discussed. These ionic liquids were shown to be recyclable. The utility of these ionic liquid solvents for high-temperature organic reactions was demonstrated.

A diastereoselective route to trans-2-aryl-2,3-dihydrobenzofurans through sequential cross-metathesis/isomerization/allylboration reactions: Synthesis of bioactive neolignans

A new highly diastereoselective synthetic route to trans-2,3-dihydrobenzofuran systems, in particular those bearing an aryl substituent at the C2 position, is described. The cornerstone of our strategy is the implementation of a cross-metathesis/isomerization/allylboration sequence starting from 2-allyl-substituted phenols and aldehydes. After an intramolecular Mitsunobu cyclization step, the anti-homoallylic alcohols allow the synthesis of the desired skeleton in a stereoselective fashion. As an illustration, we used this strategy for the preparation of the dihydrodehydrodiconiferyl alcohol (1a), a natural dihydrobenzofuran neolignan, as well as for a formal synthesis of its O-demethylated derivative 1b. An enantioselective version of this approach employing a chiral phosphoric acid in the allylboration step is also studied.

Enantioselective synthesis of benzofurans and benzoxazines via an olefin cross-metathesis-intramolecular oxo-Michael reaction

Chiral phosphoric acid and Hoveyda-Grubbs II were found to catalyze an olefin cross-metathesis-intramolecular oxo-Michael cascade reaction of the ortho-allylphenols and enones to provide a variety of benzofuran and benzoxazine derivatives in moderate to good yields and enantioselectivity.

Dialkoxybenzene and dialkoxyallylbenzene feeding and oviposition deterrents against the cabbage looper, trichoplusia ni: Potential insect behavior control agents

The antifeedant, oviposition deterrent, and toxic effects of individual dialkoxybenzene compounds/sets and of hydroxy- or alkoxy-substituted allylbenzenes, obtained through Claisen rearrangement of substituted allyloxybenzenes, were assessed against the cabbage looper, Trichoplusia ni, in laboratory bioassays. Most of the compounds/sets strongly deterred larval feeding, with some exhibiting mild toxic and oviposition deterrent effects as well. Some of the compounds/sets were more active than the commercial insect repellent, DEET (N,N-diethyl-m-toluamide), as both feeding and oviposition deterrents against the cabbage looper. On the basis of the obtained oviposition data a general hypothesis was proposed regarding the oviposition sites: one binding mode with the alkyl and allyl groups on the same side of the benzene ring resulted in deterrence, the other with alkyl and allyl groups on opposite sides of the benzene ring resulted in stimulation. The results suggest some structure-activity relationships useful in improving the efficacy of the compounds and designing new, nontoxic insect control agents for agriculture.

METHODS AND COMPOSITIONS FOR CONTROL OF CABBAGE LOOPER, Trichoplusia ni

The invention provides in part dialkoxybenzene compounds for controlling infestation by a Trichoplusia ni, and methods thereof. The compounds include a compound of Formula I: where R1 may be methyl, ethyl, propyl, n-butyl, isopentyl(3-methylbutyl) or allyl; R2 may be at positions 2, 3 or 4 and may be H, methyl, ethyl, propyl, n-butyl, isopentyl(3-methylbutyl) or allyl; and R3 may be optionally present at positions 2, 3 and 4, and is allyl; except that when R2 is at position 2, R3 if present is at position 3, and when R2 is at position 3, R3 if present is at positions 2 or 4, and when R2 is at position 4, R3 if present is at position 2, and when R2 is at position 4 and R3, if present, has reacted with an OH group at position 1 in a Markovnikov sense, then R3 becomes R4, a dihydrofuran.

Agonists and antagonists of antennal responses of gypsy moth (Lymantria dispar) to the pheromone (+)-disparlure and other odorants

Insects use the sense of smell to guide many behaviors that are important for their survival. The gypsy moth uses a pheromone to bring females and males together over long distances. Male moth antennae are equipped with innervated sensory hairs that selectively respond to pheromone components and other odors. Host plant odors, in particular, are detected by moths and sometimes cause an enhancement of the antennal and behavioral responses of the moths to their pheromone. Inspired by naturally occurring agonists and antagonists of insect pheromone responses, we have screened, by electroantennogram (EAG) recordings, a collection of compound sets and of individual compounds. We have detected interference of some compounds with the EAG responses of male gypsy moth antennae to the pheromone. We describe three activities: (1) short-term inhibition or enhancement of mixed compound + pheromone plumes, (2) long-term inhibition of pure pheromone plumes following a mixed compound + pheromone plume, and (3) inhibition of the recovery phase of mixed compound + pheromone plumes. Long-term inhibition was robust, decayed within 30 s, and correlated with the inhibition of recovery: for both activities clear structure-activity patterns were detected. The commercial repellent N,N-diethyltoluamide (DEET) was included for comparison. The most active and reproducible short-term inhibitor was a mixture of 1 -allyl-2,4-dimethoxybenzene and 2-allyl-1,3-dimethoxybenzene. The most active long-term inhibitors were a set of 1-alkoxy-4-propoxybenzenes, DEET, and 1-ethoxy-4-propoxybenzene. DEET was more specific in the olfactory responses it inhibited than 1-ethoxy-4-propoxybenzene, and DEET did not inhibit recovery, whereas 1-ethoxy-4-propoxybenzene did. Target sites for the three activities are discussed.

Microwave activation of alumina and its use as a catalyst in synthetic reactions

Microwave irradiation is a simple and efficient method of activating gamma alumina. Alumina activated in this manner is an excellent medium in which to carry out the Diels-Alder reaction and, in conjunction with additional microwave irradiation, the Claisen rearrangement. Several 2-allylphenols formed in the Claisen rearrangement rapidly undergo ring closure on alumina to form dihydrobenzofurans demonstrating the Br0nsted acidity of the solid.

Microwave-accelerated Claisen rearrangement in bicyclic imidazolium [b-3C-im][NTf2] ionic liquid

With microwaves, a chemically stable ionic liquid [b-3C-im][NTf2] recently developed in our laboratory was used as solvent and successfully applied to accelerate Claisen rearrangement reactions at high temperatures. In the presence of Lewis acid MgCl2, these thermal rearrangements could be achieved in similar reaction times but at lower temperature. For the microwaved reactions studied in this work, without scarifying isolated yields, the reaction times were significantly reduced from hours (by conventional heating) to ≤3 min. Our result also demonstrated that [b-3C-im][NTf2] ionic liquid was a useful solvent substitute and could be recycled multiple times for the studied rearrangement reaction at elevated temperatures.

Boron trichloride mediated regioselective Claisen rearrangement of resorcinol derivatives: Application to resorcinol carvonyl ethers

Claisen rearrangement (CR) of resorcinol allyl ethers was examined. Although thermal CR gave low regioselectivity, the selectivity was much improved in the presence of a Lewis acid such as boron trichloride. This rearrangement was successfully applied to resorcinol carvonyl ethers for the regioselective introduction of a carvone unit into the resorcinol skeleton for the synthesis of phytoestrogenic miroestrols. Georg Thieme Verlag Stuttgart.

Silver-catalyzed asymmetric synthesis of 2,3-dihydrobenzofurans: A new chiral synthesis of pterocarpans

2,3-Dihydrobenzofurans can be diastereoselectively prepared by condensation of aromatic aldehydes with 2,3-dihydrobenzoxasilepines under the catalysis of Ag1 complexes, and in the presence of a source of fluoride ion. The application of this st