Propynyl ethers

Cinnamyl—sesamol ethers, eg (35), are useful as insect chemosterilants (111). 3,4-Methylenedioxyphenyl-3-halo-2-propynyl ethers (36, X = halogen) are synergists for carbamate insecticides (112). HaloaLkyl or haloalkenyl ethers, eg (37), show acaricidal and insect juvenile hormone activity (113). The first total synthesis of gibbereUic acid was from 2-methoxy-6-aLkoxyethyl-l,4-benzoquinone, a derivative of hydroxyhydroquinone (114). 

Hie Pd-catalysed coupling of aiyl and heteroaryl halides with 2-hydroxyphenyl 2-propynyl ethers leads to (Z)-2-arylidene-l,4-benzodioxanes <96CC1067>. 

Dimethyl-l-nitro-l-butyne, 2395 Diphenylethyne, 3634 Di(l-propynyl) ether, 2326 Di(2-propynyl) ether, 2327... 

Diphosphinoethane, 0953 Diphosphoryl chloride, 4162 Dipotassium /(-cyclooctatetraene, 2942 Dipotassium diazirine-3,3-dicarboxylate, 1336 Dipotassium hexafluoronickelate(IV), 4357b Dipotassium aci-nitroacetate, 0668 Dipotassium phosphinate, 4425 Dipotassium triimidotellurite, 4489 Dipropargyl ether, see Di(2-propynyl) ether, 2320 f Di-2-propenyl ether, see Diallyl ether, 2425... 

It is apparent from extensive reviews of the induction of monooxygenase activity by xenobiotics that many compounds other than methylenedioxyphenyl compounds have the same effect. It may be that any synergist that functions by inhibiting microsomal monooxygenase activity could also induce this activity on longer exposure, resulting in a biphasic curve as described previously for methylenedioxyphenyl compounds. This curve has been demonstrated for NIA 16824 (2-methylpropyl-2-propynyl phenylphosphonate) and WL 19255 (5,6-dichloro-l,2,3-benzothiadiazole), although the results were less marked with R05-8019 [2,(2,4,5-trichlorophenyl)-propynyl ether] and MGK 264 [A-(2-ethylhexyl)-5-norbomene-2,3-dicarboximide],... 

Figure 3.42 a General reaction scheme for the thermal Huisgen cycloaddition b the copper-catalyzed reaction between phenyl propargyl ether (phenyl 2-propynyl ether) and benzyl azide. The catalytic reaction is performed in the presence of a reductant (sodium ascorbate) and gives just one of the product isomers in high yield. 

ROC==CCH -> ROCHjC CH. Propynyl ethers can be obtained from secondary alkoxides by reaction with trichloroethylene followed by dehydrochlorination and methylation. These can be rearranged to propargyl ethers by KAPA. This sequence is applicable to highly hindered secondary alcohols.1... 

Preparation of 2-(lH-imidazo[4,5-c]quinolin-l-yl)ethyl (2-propynyl) ether... 

The cyclopenta[c]pyran system 6 is formed when allenyl propynyl ethers are heated in CO in the presence of Co/Rh nanoparticles a Pauson-Khand reaction is involved <07SL453>. An enantioselective Bronsted acid-catalysed Nazarov cyclisation of a dihydropyran-based divinylketone affords cyclopenta[/>]pyrans 7 <07AG(E)2097> and Sc and In triflates catalyse a similar reaction of 6-alkenoyl derivatives of both dihydropyran and thiopyran <07S1733>. 

Precocene II (1) and 7-hydroxy-4-methylcoumarin were obtained from Aldrich. Acetylenic MF analog (2) was synthesized according to (27). CGA 167126 (3) was a gift from Ciba-Geigy. Insecticide synergist (.4) 2,4,5-trTchlorophenyl 2-propynyl ether was obtained from Hoffmann-La Roche. 7-Methoxy-4-methylcoumarln was obtained from Calbiochem. 

C8H14 1,2-dimethylcyclohexene 1674-10-8 411.13 34.721 1,2 14582 C8H140 tert-butyl 1-methyl-2-propynyl ether 26826-40-4 443.32 38.466 2... 

Synergists do not have to contain the MDP grouping. Other compounds showing similar activity include aryl propynyl ethers, propynyl oxime ethers, propynyl phosphorate esters and benzyl thiocyanates. 

Dipropargyl ether, see Di(2-propynyl) ether, 2327 f Di-2-propenyl ether, see Diallyl ether, 2431... 

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