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| | 3-Methyl-2-cyclohexen-1-one Basic information |
| | 3-Methyl-2-cyclohexen-1-one Chemical Properties |
| | 3-Methyl-2-cyclohexen-1-one Usage And Synthesis |
| Description | May be prepared by acid hydrolysis and decarboxylation of the
corresponding 4-carbetoxy derivative; by oxidation of 1-methylcyclohex-l-ene with chromium trioxide in acetic acid; by cyclization of 3-carbetoxy-6-chlorohept-5-en-2-one with sulfuric acid. | | Chemical Properties | CLEAR VERY SLIGHTLY YELLOW TO BROWN LIQUID | | Chemical Properties | 3-Methyl-2-cyclohexen-1-one is a nonaromatic cyclic ketone with a medicinal, phenolic, mild cherry aroma | | Occurrence | Reported found in oil of Mentha pulegium, cocoa, coffee, filbert, sweet corn, dried bonito, katsuobushi, wild
rice and clam. Also produced by some animals in vivo | | Uses | 3-Methyl-2-cyclohexen-1-one was used in the synthesis of 19-nor-1α, 25-dihydroxyvitamin D(3) derivatives. It was also used in sex pheromone of the Douglas-fir beetle. Used in nut flavor. | | Uses | 3-Methyl-2-cyclohexenone is an insect sex pheromone of the Douglas-fir beetle. It can be used as a starting material:
- In the total synthesis of (?)-ar-tenuifolene, a naturally occurring aromatic sesquiterpene.
- To synthesize an organic building block 2-trimethylsilyl-3-methyl-cyclohexenone.
- In the total synthesis of natural diterpenoids (+)-taiwaniaquinone H and (+)-dichroanone.
| | Definition | ChEBI: 3-Methyl-2-cyclohexen-1-one is a cyclic olefin. | | Preparation | By acid hydrolysis and decarboxylation of the corresponding 4-carbetoxy derivative; by oxidation of 1-methylcyclohex-1-ene with chromium trioxide in acetic acid; by cyclization of 3-carbetoxy-6-chlorohept-5-en-2-one with sulfuric
acid. | | Aroma threshold values | Aroma characteristics at 2.0%: sweet, nutty, phenolic, walnut, fruity, almond and benzoin | | Taste threshold values | Taste characteristics at 50 ppm: nutty, musty, phenolic and woody with grain-like nuances. | | Synthesis Reference(s) | Journal of the American Chemical Society, 101, p. 494, 1979 DOI: 10.1021/ja00496a044
The Journal of Organic Chemistry, 42, p. 1349, 1977 DOI: 10.1021/jo00428a017
Tetrahedron Letters, 17, p. 3, 1976 |
| | 3-Methyl-2-cyclohexen-1-one Preparation Products And Raw materials |
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