Cyclopropanecarboxylic acid

A solution of the above ester (207.8 grams) and 64.5 grams of sodium hydroxide in 80 cc of water and 600 cc of ethanol is refluxed for 9 hours. The carboxylic acid of 2-phenyl-cyclopropane is liberated with 200 cc of concentrated hydrochloric acid. The 2-phenyl-cyclopropanecarboxylic acid contains 3 to 4 parts of the trans isomer to 1 part of the cis isomer. The acid is recrystallized from hot water. The pure trans isomer comes out as crystalline material (solid) while the cis isomer stays in solution. 

Cyclopentyl- 3-(N-piperidyl)ethyl ketone Cycrimlne HCI /3-Cyclopentyl propionic acid Testosterone 17/3-cypionate Cyclopentyl (tt-thienyl) hydroxy acetic acid Penthienate bromide Cyclopropanecarboxylic acid chloride Prazepam... 

Twenty-four grams (0.11 mole) of red mercuric oxide (Note 1) and 60 ml. of freshly distilled 1,1,2,2-tetrachloroethane are placed in a 250-ml. three-necked flask equipped with a dropping funnel, a reflux condenser, and a stirrer. A solution of 32.2 g. (0.20 mole) of bromine and 17.2 g. (0.20 mole) of cyclopropanecarboxylic acid in SO ml. of tetrachloroethane is added dropwise to the stirred suspension of mercuric oxide over a period of 45 minutes, the flask being kept in a water bath at 30-35° (Note 2). The mixture is stirred after the addition of the reactants until the evolution of carbon dioxide ceases. 

Bromocyclopropane has been prepared by the Hunsdiecker reaction by adding silver cyclopropanecarboxylate to bromine in dichlorodifluoromethane at —29° (53% yield) or in tetrachloro-ethane at —20° to —25° (15-20% yield).3 Decomposition of the peroxide of cyclopropanecarboxylic acid in the presence of carbon tetrabromide gave bromocyclopropane in 43% yield.4 An attempt to prepare the bromide via the von Braun reaction was unsuccessful.3... 

Bidret, 1 -PHENY L-2-THIO-, 42, 87 Brominadon, nuclear, aluminum chloride as catalyst for, 40, 7 of cyclopropanecarboxylic acid to bromocvclopropane, 43, 9 of phthalide using N-bromosuccin-imide, 42, 26... 

The protocol is effective in preparation of hydrazides of 5 carbons or less. Cyclopropanecarboxylic acid hydrazide15 and isobutyric acid hydrazide16 were prepared from their corresponding acid chlorides in 64% and 71% yields, respectively. However, when this method was applied to cyclohexanecarboxylic acid chloride, the bis-acylhydrazide was the predominant product, and the mono-acylhydrazide17 was isolated in 25% yield.18... 

C4H5CIO 4023-34-1) see Buprenorphine Fexofenadine hydrochloride Naltrexone Prazepam cyclopropanecarboxylic acid ethyl ester (C(,H o02 4606-07-9) see Pimozide... 

In contrast to the synthesis of carbocyclic rings, the Cope rearrangement has been used sparsely for generating azepinones. Recently, the enantioselectivity of the conversion of 2-aza-divinylcyclopropane 286 has been investigated. The synthesis started from the optically active cyclopropanecarboxylic acid (90% ee), which had been converted into the isocyanate 286 by initial azidation to 285 and a consecutive Curtius rearrangement. Furthermore, the conditions of the iso-... 

GABAc receptors are defined by their insensitivity to bicuculline and their activation by conformationally restricted analogues of GABA such as CACA and (+)-CAMP (15, 2i -2-(aminomethyl)cyclopropanecarboxylic acid). They are blocked by picrotoxin but can be selectively antagonised by TPMPA (l,2,5,6-tetrahydropyridin4-ylphosphinic acid). Unlike GABAa receptors, they are not affected by benzodiazepines, barbiturates or anaesthetics (Barnard et al. 1998 Bormann 2000 Chebib and Johnston 2000). 

Schiller JG, AE Chung (1970) Mechanism of cyclopropane ring cleavage in cyclopropanecarboxylic acid. J Biol Chem 245 6553-6557. 

Cyfluthrin-met/ty/-fi(6 (provided in acetonitrile solution by Bayer Corp.) Cyfluthrin stable-isotope internal standard (IS), Cyclopropanecarboxylic acid, 3-(2,2-dichloroethenyl)-2,2-dimethyl-, cyano(4-fluoro-3-Phenoxyphenyl)methyl ester-met/tyWe, molecular formula C22H12D6CI2FNO3, molar mass 440.3, ion observed at 213.0 (GC/MS)... 

The solution is then cooled in an ice bath and acidified by 200 g. of concentrated sulfuric acid (sp. gr. 1.84) previously mixed with 300 g. of cracked ice. The solution is again cooled in an ice bath. The thick floating layer of cyclopropanecarboxylic acid and various polymers is separated and the cold aqueous solution extracted once with 1 1. of ether, using a stirrer instead of shaking (Note 5). The extract and crude acid are combined and dried over SO g. of Drierite, and the solvent is removed in a 500-ml. modified Claisen flask2 on a steam bath. The residue is then distilled under reduced pressure. The yield of acid boiling at 94-95°/26 mm. or 117—118°/75 mm. is 63.5-68 g. (74-79%) (Note 6). 

Cyclopropanecarboxylic acid has been prepared by the hydrolysis of cyclopropyl cyanide,3 although it is unnecessary to... 

Reaction of 2,3-dichloroquinoxaline 367 with sodium azide in ethanol has been used to synthesize bistetrazolo-[l,5- 5, l -c]quinoxaline 368 in 65% yield (Scheme 28) <1997JOC4082>. Similarly, reaction of 2,3-dichloroquinoxaline 367 with thiosemicarbazide 366 has been used to generate l,6-diamino-bis-l,2,4-triazolo[4,3- 3,4-f]quinoxaline 365 in 67% yield <2002AP389>. Condensation of cyclopropanecarboxylic acid hydrazide 369 meanwhile gives rise to the cyclopropyl-substituted tetracycle 370 in 93% yield in the presence of l,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as base (Scheme 28) <2005JOC2878>. 

Methyl 2,2-dimethyl-3-(trimethyl iloxy)-1-cyclopropanecarboxylate Cyclopropanecarboxylic acid, 2,2-dimethyl-3-[(trimethylsilyl)oxy]-, methyl ester (10) (77903-45-8)... 

Fig. 8 Modification of the acid moiety, (a) Cyclopropanecarboxylic acid esters, (b) Non-cyclopropanecarboxylic acid esters...

Martel J, Tessier J, Demoute JP (1978) New esters of cyclopropanecarboxylic acids with a polyhalogenated substituent, preparation and pesticidal compositions. Ger Offen 2,742,546... 

Menthol ester (20) with (l/ S)-frans-2,2-dimethyl-3-(2,2-dichloroethenyl) cyclopropanecarboxylic acid (19) has been utilized to produce ( R)-trans-2, 2-dimethyl-3-(2,2-dichloroethenyl) cyclopropanecarboxylic acid (21), an acid moiety of transfluthrin (22) [9]. Matsuo et al. surveyed various optically active secondary alcohols for their potential in the optical resolution of (lRS)-trans-chrysanthemic acid [10] (Scheme 2). 

Schiller JG, Chung AE (1970) The metabolism of cyclopropanecarboxylic acid. J Biol Chem 245 5857-5864... 

CYCLOPROPANECARBOXYLIC ACID, cis-2-PHENYL-, 50, 94 Cyclopropane derivatives, synthesis, 52, 22, 33, 132 Cyclopropenes, 50, 30 Cyclopropenone, di-tert-buty1-,... 

In a recent study, chiral separations for pyrethroic acids, which are the chiral building blocks of synthetic pyrethroids and the primary metabolites of the acid part of these potent ester insecticides, have been developed [62], For example, a polar-organic mobile phase allowed the complete baseline resolution of all four stereoisomers of chrysanthemic acid (2,2-dimethyl-3-(2-methylprop-l-enyl)-cyclopropanecarboxylic acid) on a 0-9-(tcrt-butylcarbamoyl)quinine-based CSP(acjj = 1.20, oLtrans = 1-35, critical Rs = 3.03) (Figure 1,32a). This chiral acid is the precursor of pyrethroids like allethrin, phenothrin, resmethrin, and tetramethrin but not excreted as metabolite. The primary acid metabolite of these pyrethroids is chrysanthemum dicarboxylic acid (3-[(l )-2-carboxyprop-l-enyl]-2,2-dimethylcyclopropanecarboxylic acid) the stereoisomers of which could also be resolved with a reversed-phase eluent (acetonitrile— 30-mM ammonium acetate buffer 90 10, v/v pHa = 6.0) and employing an O-9-(2,6-diisopropylphenylcarbamoyl)quinine-based CSP ads = 1-09, atrans = 1-50,... 

Table III. Biological Activity of Bridged Biphenyl and Heteroaromatic Bridged Biphenyl Esters of cis-3-(2 Chloro3.3,3-trifluoro-l-propenyl)-2,2-dimethyl-cyclopropanecarboxylic acid...

Some variations of the method have been used to prepare cyclopropyl and cyclobutyl halides. Simultaneous addition of bromine and 3-bromocyclobutanecarboxylic acid to the suspension of mercuric oxide gives 1,3-dibromocyclobutane in good yield.7 Similarly, cyclopropanecarboxylic acid gives bromo-cyclopropane,9 and 3-(bromomethyl)cyclobutanecarboxylic acid gives 3-(bromomethyl)cyclobutyl bromide.10 In the latter reaction, it was found desirable to remove the water from the reaction as it is formed in order to obtain high yields. Another variation is the addition of a mixture of the acid and mercuric oxide to excess bromine in bromotrichloromethane.6... 

In the following we shall focus on heterogeneous acid-base reactions. One of the best known case studies is the reaction of crystalline benzoic acid with ammonia to form 1 1 ammonium salts [19, 20]. Crystalline p-chlorobenzoic anhydride reacts with gaseous ammonia to give the corresponding amide and ammonium salt [22] a similar reaction has been investigated in the case of optically active cyclopropanecarboxylic acid crystals [23]. 

Cyclopentanes, synthesis, 66, 10 CYCLOPEKTANONE SYNTHESIS, 66, 87, 92, 93 Cyclopentanone, 2-carbomethoxy-3-vinyl, 66, 56 Cyclopentanone, 2-ethenyl-2-methyl (88729-76-4), 66, 94 2-CYCLOPENTEN-l-ONE, 3-METHYL-2-PENTYL-, 65, 26 Cyclopropane, l-trimethy1s1lyloxy-1-ethoxy-, 56, 44 Cyclopropanecarboxylic acid chloride, 66, 176... 

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