Cyclopropane- 1-carboxylate

The spiropyrazohnes obtained from 51 were converted into enantiopure A -pyrazoline-3-carboxylates and 1 -(hydroxyethyl)cyclopropane-1 -carboxylates (128). Those obtained from 54 and 55 were transformed into optically active a-spirocyclopropyllactones and 3-amino-3-(hydroxyethyl)pyrrolidin-2-ones (130). The spiropyrazoline obtained from a chiral propylidene-diketopiperazine and diazomethane was converted into (+)-(lR,25)-l-amino-2-ethyl)cyclopropane-l-carboxylic acid (allocoronamic acid) (135). 

Chemical Name A-a-cyano-3-phenoxybenzyl (lR,3R)-3-(2,2-dibromovinyl)-2,2-dimethyl cyclopropan-1-carboxylate CAS Registry No 52918-63-5 Uses insecticide (pyrethroid)... 

Fig. Id. Ethylene Exhylcnt 1-amino-cyclopropane-1-carboxylic acid (ACC).

ACC 1 -amino-cyclopropane- 1-carboxylic acid 2,4,5-T 2,4,5-trichlorophenoxyacetic acid... 

Enzymes may also catalyze transformations of a highly selective and nniqne natnre snch as in transformations of small molecnles. Examples are the fragmentation of 1-amino-cyclopropane-1-carboxylate to the frnit ripening hormone ethylene, the cycloreversion of thymine dimers in DNA repair, the synthesis of isopenicUhn and the rednction of molecn-lai nitrogen (N2) to ammonia... 

Because 1 mole of cyanide is produced for each mole of ethylene generated from ACC (1-amino-cyclopropane-1-carboxylic acid) see Chapter 13), all plants must contain small amounts of cyanide (Peiser et al., 1984). However, due to a concomitant increase in the amount of (3-cyanoalanine synthase, the ability to detoxify cyanide in the tissues is much higher (Manning, 1988). 

A lactone can be refunctionalized to an amino acid as well as a carboxylic acid. Reaction of 7.34 with potassium phthalimide opened the lactone ring to give a phthalimido-acid. Removal of the phthalimide group gave 2-methylamino-l-phenyl-cyclopropane-1-carboxylic acid, 7.35Amino acid 7.35 was tested as a potential antidepressant, and several aryl analogs were prepared the 4-chlorophenyl, the 4-methylphenyl, and the 4-methoxyphenyl derivatives. 

Acton GJ, Murray PB (1974) The roles of auxin and gibberellin in reversing radiation inhibition of hypocotyl lengthening. Planta 117 219-226 Adams DO, Yang SF (1979) Ethylene biosynthesis identification of 1-amino-cyclopropane-1-carboxylic acid as an intermediate in the conversion of methionine to ethylene. Proc Natl Acad Sci USA 76 170-174... 

Phenylacetic acids have been prepared from 2,2-dichlorostyrenes by sequential hydroboration and oxidation (Cr03-H2S04) of the intermediate trialkyl borane, and benzoyl benzoic acids (8), not readily available by other routes, have been obtained" in good yield by treatment of phthalic anhydride with aryl-lithiums at — lOO C. Syntheses of some bicyclo [1,1,0] butane-l-carboxylic acids (9) and a range of cyclopropane-1-carboxylic acids [(10) and (II)] have been described. 1-Hydroxy-cyclopropanecarboxylic acids (13) have been prepared from the hydroxy-cyclobutanone derivatives (12), following bromination and hydrolysis. 

X-Cyhalothrin [Cyano-(4-phenoxyphenyl)-methyl] 3-(2-chloro-3,3,3-trifluoro-prop-1-enyl)-2,2- dimethyl-cyclopropane-1-carboxylate 91465-08-6... 

Metofluthrin N A/-butylacetanilide Nonanal 2,3,5,6-Tetratluoro-4-(methoxymethyl)-phenyl]methyl 2,2-dimethyl-3-piop-1-enyl-cyclopropane-1-carboxylate 240494-70-6... 

Pyrethrin (2-Methyl-4-oxo-3-prop-2-enyl-1-cyclopent-2-enyl) 2,2-dimethyl-3-(2-methylprop-1-enyl) cyclopropane-1-carboxylate 584-79-2... 

Transfluthrin y 2,3,5,6-Tetrafluorophenyl) methyl 3-(2,2-dichloroethenyl)-2,2-dimethyl cyclopropane-1-carboxylate 118712-89-3... 

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