Chrysanthemic acid

ChEBI: A monocarboxylic acid that is cyclopropanecarboxylic acid substituted by two methyl groups at position 2 and a 2-methylprop-1-en-1-yl group at position 3.

Chrysanthemic acid is a monocarboxylic acid that is cyclopropanecarboxylic acid substituted by two methyl groups at position 2 and a 2-methylprop-1-en-1-yl group at position 3. It has a role as a plant metabolite. It is a member of cyclopropanes and a monocarboxylic acid. It derives from a cyclopropanecarboxylic acid.

There are many synthetic methods for the first chrysanthemum acid, but the current industrial production mainly includes the diazoacetate method (also known as the Harper and Campbell method) and the isopentenyl sulfone method (also known as the Martel method). The reaction equations are described below. Diazoacetate method isopentenyl sulfone method (Martel method) The ethyl chrysanthemum acid (methyl ester) obtained by the above method is hydrolyzed in an alcohol solution in the presence of a base, and then acidified to obtain chrysanthemum acid. Later, Jacqueline et al. reported that the first chrysanthemum acid can also be synthesized by the orthoacetate method. The isobutene and isobutyryl chloride are condensed under the catalysis of AlCl3 to obtain 2, 5-dimethylhexen-2-one-3, which is reduced by NaBH4 and reacted with orthoacetate to obtain 3, 3, 6-trimethylheptane Ethyl ene-4-acid is reacted with chlorine gas, dehydrochlorination and cyclization are followed to obtain (±) cis-trans first chrysanthemum acid ethyl ester, which is mainly trans isomer. Put the lye of ethyl chrysanthemum acid (methyl) and ethanol (or methanol) into the reaction flask separately, reflux for 4-6 hours under heating and stirring, and recover the ethanol (methanol) under normal pressure. The recovered alcohol can be used to remove the alcohol. The reaction solution is acidified with hydrochloric acid, and then extracted with toluene or benzene, the organic layer is separated, washed with water, dried, and desolvated to obtain chrysanthemum acid, which is waxy or solid, with a yield of 96%-97%.

The first chrysanthemum acid is referred to as chrysanthemum acid, the chemical name is (±)cis-trans-2,2-dimethyl-3-(2-methylpropenyl)cyclopropanecarboxylic acid [(±)cis,trans-2,2 -dimethyl-3-(2-methyl-1-propenyl)cyclopropane carboxylic acid] is an important intermediate for pyrethroids and can be used to synthesize allethrin, promethrin, permethrin, pyrethrin, Pyrethroids such as methrin, cypermethrin, methrin, phenfenthrin, fenvalerate, fenvalerate, etc.

Molecular Weight:168.23
XLogP3:3.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:168.115029749
Monoisotopic Mass:168.115029749
Topological Polar Surface Area:37.3
Heavy Atom Count:12
Complexity:234
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes