cyclopropane

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cyclopropane,

C3H6, a gaseous hydrocarbon. It is a cyclic alkane, its three carbon atoms being joined together in a ring. The angle between successive carbon-carbon bonds in the ring is only 60°, much less than that between successive carbon-carbon bonds in a normal open-chain alkane; the cyclopropane molecule is thus said to be "strained." Many reactions of cyclopropane involve breaking one of the carbon-carbon bonds in the ring, which opens the ring and relieves the strain. Cyclopropane is prepared commercially by the reaction of 1,3-dichloropropane with zinc. It is a potent inhalation anesthetic, that once enjoyed wide use, but has been replaced by less combustible gases. Cyclopropane allowed the transport of more oxygen to the tissues than did other common anesthetics and also produced greater skeletal muscle relaxation. It is not irritating to the respiratory tract. Because of the low solubility of cyclopropane in the blood, postoperative recovery was usually rapid but nausea and vomiting were common. See anesthesiaanesthesia
[Gr.,=insensibility], loss of sensation, especially that of pain, induced by drugs, especially as a means of facilitating safe surgical procedures. Early modern medical anesthesia dates to experiments with nitrous oxide (laughing gas) by Sir Humphry Davy of England
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Cyclopropane

 

(also trimethylene), an alicyclic hydrocarbon having the structural formula

Cyclopropane is a colorless gas with a boiling point of –32.8°C and a density of 0.720 g/cm3 at –79°C. Insoluble in water, it is soluble in alcohol and ether.

Cyclopropane is the first member of the homologous series of cycloparaffins. Its trimethylene ring, however, is characterized by reactions of the C═C double bond; for example, it forms 1,3-dibromopropane (BrCH2CH2CH2Br) in its reaction with bromine. The cyclopropane ring is easily broken because it is strained. Nevertheless, in contrast to olefins, cyclopropane does not react with potassium permanganate and ozone at 20°C. Cyclopropane and hydrocarbons containing the cyclopropane ring may be obtained by reacting zinc dust with derivatives that have two halogens attached at the 1 and 3 positions. They may also be obtained by other methods, including the joining of carbenes to olefins.

Cyclopropane and its derivatives are of great theoretical interest; for example, it has been discovered that compounds containing the cyclopropenyl cation have aromatic properties. The cyclopropane ring is found in biologically important natural compounds (seePYRETHRINS). Cyclopropane itself is used as an anesthetic.

cyclopropane

[¦sī·klō′prō‚pān]
(organic chemistry)
C3H6 A colorless gas, insoluble in water; used as an anesthetic.
References in periodicals archive ?
263) A cyclopropyl group is comprised of three carbons that form a strained, three-membered ring.
7 EC, Electrical conductivity; OC, organic carbon; CCE, calcium carbonate equivalents; SAR, sodium absorption ratio; G , G+, Gram-negative and -positive bacteria; PLFAs, phospholipid fatty acids; cy/pre, ratio of the sum of cyclopropyl PLFAs to the sum of their monoenoic precursors; S/M, ratio of the sum of saturated to the sum of monounsaturated PLFAs Property Component PC 1 PC 2 EC 0.
Since the rearrangement product (shown to be an alpha-glycoside) was a mixture of two diastereomers only, it was possible to separate them and obtain both enantiomers of our starting [beta]-lactam, Glycals can also be used for conversion to cyclopropyl derivatives.
The ratio of cyclopropyl fatty acids to their precursors, a PLFA indicator of stress, decreased in the treatments with bone meal and oyster shell (Table 4).
SYNTHESIS OF CYCLOPROPYL PEPTIDOMIMETICS AS POTENTIAL BACE AND HCV NS3-4A PROTEASE INHIBITORS.
7 kJ/mol) difference in binding of these compounds to the yeast enzyme could result from either the introduction of a more favourable hydrogen bond(s) or the addition of an extra hydrophobic interaction between the cyclopropyl [CH.
This triggers a cascade of free radical reactions leading to the ring opening of the cyclopropyl moiety in competition with hydrogen abstraction.
33 3-Methyl-2-butanone, 1-pentanol, 2,3-dichloro-l-propene, >30 1,2,4-tifluorobenzene, 1-butanol, 2-pentanol, 1,3-dichlorotetrafluoro-2-propanone, 1,4-dioxane, n-propyl acetate, methoxyflurane (pentrane), 4-methyl-2-pentanone, 2-chloroethyl-ethyl ether, dibromomethane, cyclopropyl methyl ketone, tetrachloroethylene, 2-Chloro-2-methyl-2-propanol Table 3.