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Cyclopropane-carboxylic acid, CAS Number: 1759-53-1

In vegetal, a great variety of molecular forms of dicarboxylicacids are found :

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3-trifluoropropenyl) cyclopropane carboxylic acid.

Finally, hydrolysis of the carbamate 23 with 6N sodium hydroxideunder reflux and purification through cationic ion exchange resin gave (1)-1-amino-2,2-dimethylcyclopropane-1-carboxylicacid 4. The absolute stereochemistry of the compound obtained was assessed bydirect comparison to reported data of its optical rotation. The enantiomeric excess (>98%) was determined by analytical reverse phase HPLC after derivatization with ()-Mosher'sacid chloride.

Synthesis of optically active1-amino-2,2-dimethylcyclopropane-1-carboxylic acid

The smallest member of these cyclopropane containing amino acids,1-aminocyclopropane-1-carboxylic acid 1 is known to be the biochemical precursor ofthe plant hormone ethylene in a process catalysed by the ethylene forming enzyme (EFE) . Ethylene, once liberated, induces acceleration of most of the plantdevelopment processes, such as flowering, ripening, germination and senescence . Substances that inhibit the ethylene forming enzyme would allow aneffective control on the growth of plants, thus being of greatest importance toagriculture .

1-Aminocyclopropanecarboxylic acid | C4H7NO2 - …

Enzyme mediated synthesis of (1)-1-amino-2,2-dimethylcyclopropane-1-carboxylicacid

Synthesis and study of 1-substituted tricyclo[,4]nonanesAU - Chenier,Philip J.AU - Jenson,Todd M.AU - Wulff,William D.PY - 1982Y1 - 1982N2 - Acidity studies on tricyclo[,4]nonane-1-carboxylic acid (16-COOH) vs.

The next step was the Curtius rearrangement of (1)-2,2-dimethyl-1-(2,2,2-trifluoroethoxycarbonyl)-cyclopropane-1-carboxylicacid 22 with diphenylphosphoroazidate (DPPA) . After work-upwith ethanol, this reaction afforded the optically active carbamate (1)-2,2,2-trifluoroethyl2,2-dimethyl-1-(N-ethoxycarbonylamino)-cyclopropane-1-carboxylate 23.

Cyclopropane carboxylic acid derivatives - Patent - …

T1 - Synthesis and separation of substituted cyclopropane carboxylic acid amide isomers

A facile and highly stereoselective synthesis of (1)-1-amino-2,2-dimethylcyclopropane-1-carboxylicacid 4 via pig liver esterase (PLE) catalysed hydrolysis of a prochiral2,2-dimethylcyclopropane-1,1-diester is described in the present report. Pig liveresterase has been reported to selectively hydrolyse some rigid, prochiral malonic esters .

First, the enzymatic asymmetrization of dimethyl2,2-dimethylcyclopropane-1,1-dicarboxylate 19 was attempted. The diester wasprepared by Michael-induced ring closure (MIRC) of the brominated alkylidene malonate 18 with sodium borohydride in methanol. The diester was dispersedin pH 7.0 phosphate buffer at 30°C and enzyme (pig liver esterase) was added. Thisenzymatic hydrolysis gave the corresponding monoacid 16, but in low enantiomericexcess (ca. 65%).

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  • cyclopropane carboxylic acid, 1759-53-1 - The Good …

    bicyclo[2.2.2]octane-1-carboxylic acid (17-COOH) show a slight inductive withdrawal by the cyclopropane ring.


    Cyclopropylcarboxylic Acid

  • into bicyclic cyclopropane carboxylic acid lactones ..

    Cyclopropane-carboxylic acid - chemical information, properties, structures, articles, patents and more chemical data.

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Accumulation of 1-(malonylamino)cyclopropane-1-carboxylic acid in ..

Kirihata et al. described the fractionalcrystallisation of the diastereoisomeric salts of2,2-dimethyl-1-formylaminocyclopropane-1-carboxylic acid with (-)-quinine.

(malonylamino)cyclopropane-1-carboxylic acid ..

Suberic acid, nonanedioic acid (and its mono-unsaturated derivative:2-nonenedioic acid), decanoic acid (and its mono-unsaturated derivative:2-decenedioic acid) are present in honey () and are of special interest becausethey have long been recognized as part of the pheromone system of the honeybee (). They are producedin the mandibular glands of the queen and the worker honeybees, they regulatetheir activities in the hive.

It was shown that all these dicarboxylic acids are formed during the dryingprocess of and that thedetermination of these decomposition products may be of value in determining theage of old samples.

The higher weight dicarboxylic acids (n=10 to 21) are found in different plant lipids, particularly in what was named erroneously (triglycerides containing C20, 21, 22 and 23 dicarboxylic acids besides normal fatty acids) from the sumach tree (Rhus sp.). Among them, Thapsic acid (n=14) was isolated from the dried roots of the Mediterranean "deadly carrot", Thapsia garganica (Umbelliferae), but others, as Brassylic acid (n=11), were prepared chemically from different sources.
Brassylic acid can be produced chemically from erucic acid by ozonolysis but also by microorganisms () from . This diacid is produced on a small commercial scale in Japan for the manufacture of fragrances.
A review on the applications and the industrial biotechnology of these moleculeshas been released by Kroha K ().

A large survey of the dicarboxylic acids present in Mediterranean nuts revealed unusual components (). A total of 26 minor acids (from 2 in pecan to 8% in peanut) were determined : 8 species derived from butanedioic acid, likely in relation with photosynthesis, and 18 species with a chain from 5 to 22 carbon atoms.

Higher weight acids (>C20) are found in present at vegetal surfaces (outer bark, root epidermis). C16 to C26

2,2-Dimethyl cyclopropyl carboxylic acid: ..

Accordingly, a set of activated esters derived from -halogenatedalcohols was evaluated as prochiral precursors for the PLE hydrolysis. The inductiveeffect of the halogen atoms would render the corresponding diesters more reactive towardsenzymatic hydrolysis. The diesters were prepared by double saponification of dimethyl2,2-dimethylcyclopropane-1,1-dicarboxylate 19 with sodium hydroxide at roomtemperature for five days. The resulting 2,2-dimethylcyclopropane-1,1-dicarboxylic acid 20 was then esterified with a -halogenatedalcohol in dichloromethane in the presence of dicyclohexylcarbodiimide (DCC) and4-(N,N-dimethylamino)pyridine (DMAP) .

(2-methylprop-1-enyl)cyclopropane-1-carboxylic acid', ..

All the reported syntheses rely on the use of chiral precursors andauxiliaries, and in the resolution of racemic mixtures. Here, we report the firstenantioselective synthesis of (1)-1-amino-2,2-dimethylcyclopropane-1-carboxylicacid (4) by an enzymatic asymmetrization of a prochiral precursor.

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