Topic
Methyl vinyl ketone
About: Methyl vinyl ketone is a research topic. Over the lifetime, 1510 publications have been published within this topic receiving 26839 citations. The topic is also known as: 3-buten-2-one & gamma-oxo-alpha-butylene.
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Patent•
05 Mar 1984
TL;DR: In this article, a perfume composition containing an omega-alkenyl methyl ketone expressed by the formula (n is an integer 5-10) is proposed, where the amount to be incorporated in the perfume composition is preferably within 0.001-20wt% range based on the total composition.
Abstract: PURPOSE:An excellent perfume composition, containing an omega-alkenyl methyl ketone, having green note making a person remember for fleshlike feeling of a tropical fruit, e.g., a mango, or melon, and mild sweetness, a floral aroma, e.g. hop, and having improved lasting property. CONSTITUTION:A perfume composition containing an omega-alkenyl methyl ketone expressed by the formula (n is an integer 5-10). Specific examples of the compound expressed by the formula include 9-decen-2-one, 10-undecen-2-one and 11-dodecen-2-on, etc. The amount to be incorporated in the perfume composition of the compound expressed by the formula is preferably within 0.001-20wt% range based on the total composition. The compound expressed by the formula is synthesized by using the 1,4-addition reaction of methyl vinyl ketone with a Grignard reagent of an alpha-halogeno-omega-alkene. For example, the 9-decen-2-one is synthesized by reacting the methyl vinyl ketone with 5-hexenylmagnesium bromide in the presence of a cuprous chloride catalyst in a solvent at -10 deg.C.
4 citations
TL;DR: The total synthesis of dl-aspterric acid has been accomplished as mentioned in this paper, which is the degradation product of 1.5% HCl and 1.1% HCL.
Abstract: Total synthesis of dl-aspterric acid (1) has been accomplished. Robinson annulation of the keto ester (2) with methyl vinyl ketone, followed by reduction with LiAlH4 and oxidation with MnO2, afforded the enone alcohol (4), which was converted to the hydroxy-ether (6) via three steps (I2-Ag2O, AgOAc, and alkaline hydrolysis). Successive treatment of 6 with tert-butyldimethylsilyl chloride, tert-BuOK-MeI, NaBH4, Ac2O-pyridine and 5% HCl afforded the hydroxy acetate (18). The hydroxy acetate (18) was converted to the hydroxy ketone (20) via catalytic hydrogenation under medium pressure, Jones oxidation, and alkaline hydrolysis. Treatment of 20 with PCl5 gave the norketone (21), which is the degradation product of 1. The dimethylacetal (25) of 20 was treated with Me3SiCN-SnCl2 to give the methoxy cyanides A (26) and B (27). The major methoxy cyanide B (27) was successively treated with KOH, Me3SiCl-NaI, Ac2O, and 5% HCl to give the monoacetate (31), which was finally converted to 1 via ring contraction with PCl5 and alkaline hydrolysis.
4 citations
TL;DR: In this article, the aza-Baylis-Hillman reaction of N-sulfonated imines with methyl vinyl ketone, ethyl vinyl ketone, and acrolein was shown to yield good yields with good to high ee (70-95% ee) at low temperature (approximately -30 to -20 degrees C) or at room temperature in THF.
Abstract: In the aza-Baylis-Hillman reaction of N-sulfonated imines (N-arylmethylidene-4-methylbenzenesulfonamides and others) with methyl vinyl ketone, ethyl vinyl ketone, and acrolein, we found that, in the presence of a catalytic amount of chiral phosphine Lewis base such as (R)-2'-diphenylphosphanyl-[1,1']binaphthalenyl-2-ol LB1 (10 mol %) and molecular sieve 4A, the corresponding aza-Baylis-Hillman adducts could be obtained in good yields with good to high ee (70-95% ee) at low temperature (approximately -30 to -20 degrees C) or at room temperature in THF, respectively. In CH2Cl2 upon heating at 40 degrees C, the aza-Baylis-Hillman reaction of N-sulfonated imines with phenyl acrylate or naphthyl acrylate gave the adducts in good to high yields (60-97%) with moderate ee (52-77%). The mechanistic insight has been investigated by 31P and 1H NMR spectroscopic measurements. The key enolate intermediate, which has been stabilized by intramolecular hydrogen bonding, has been observed by 31P and 1H NMR spectroscopy. An effective bifunctional Lewis base and Bronsted acid phosphine Lewis base system has been disclosed in this catalytic, asymmetric aza-Baylis-Hillman reaction.
4 citations
TL;DR: Their structures and configurations have been elucidated by 1H-NMR and 13C NMR spectroscopy for (Z/E)-2b and (Z)-2d also by conversion into (r-4.6)-trisubstituierte 1.3.
4 citations
TL;DR: In this article, a general method of synthesis of the title compounds was proposed, based on the reaction of methyl 7methoxy-2-oxotetralin-1-carboxylate (2a) with methyl vinyl ketone in the presence of benzyltrimethylammonium methoxide catalyst.
Abstract: The reaction of methyl 7-methoxy-2-oxotetralin-1-carboxylate (2a) with methyl vinyl ketone in the presence of benzyltrimethylammonium methoxide catalyst yielded the expected tricyclic keto alcohol (3a) and the latter on dehydration with p-toluenesulphonic acid gave the unsaturated ketone (la). This constitutes a general method of synthesis of the title compounds. When sodium methoxide was used as the catalyst in the above reaction, (la) was not obtained.
4 citations