50373-59-6Relevant articles and documents
PROCESSES FOR PREPARING 2-ISOPROPENYL-5-METHYL-4-HEXENOIC ACID, 2-ISOPROPENYL-5-METHYL-4-HEXEN-1-OL, AND A CARBOXYLATE ESTER THEREOF
-
, (2021/10/22)
The present invention provides a process for preparing 2-isopropenyl-5-methyl-4-hexenoic acid of the following formula (4), comprising steps of: subjecting a Grignard reagent of the following general formula (1), wherein R1 represents a linear, branched, or aromatic monovalent hydrocarbon group having 1 to 8 carbon atoms, and X represents a chlorine atom, a bromine atom, or an iodine atom, and 1,1,1,3,3,3-hexamethyldisilazane to a deprotonation reaction to form a 1,1,1,3,3,3-hexamethyldisilazane derivative; and subjecting 2-methyl-3-buten-2-yl 3-methyl-2-butenoate of the following formula (3) to a rearrangement reaction in the presence of the 1, 1, 1,3,3,3-hexamethyldisilazane derivative to form 2-isopropenyl-5-methyl-4-hexenoic acid (4).
Identification of the sex pheromone of the mealybug Dysmicoccus grassii Leonardi
De Alfonso, Ignacio,Hernandez, Estrella,Velazquez, Yisell,Navarro, Ismael,Primo, Jaime
, p. 12959 - 12964 (2013/02/23)
Studies about the sex pheromone of the mealybug Dysmicoccus grassii, a main pest of Canary Islands banana cultivars, showed strong evidence that (-)-(R)-lavandulyl propionate and acetate in a 6:1 ratio are principal components of it. Volatile collection and GC-MS analysis from aeration of virgin females allowed the structural elucidation of the compounds. The activity and stereochemistry of both substances were established by means of relative attraction of mealybug males to synthetic standards in competitive Petri dish bioassays. (R)-Lavandulyl propionate induced a stronger attractive effect when compared to (R)-lavandulyl acetate. The attractiveness of the mixture of the two compounds at the original source ratio showed no statistically significant difference from that of the sum of each of the single compounds alone, suggesting that both components are not synergistic but additive.
Chemomicrobial synthesis of (R)- and (S)-lavandulol
Gliszczynska, Anna,Bonikowski, Radoslaw,Kula, Jozef,Wawrzenczyk, Czeslaw,Ciolak, Kornelia
, p. 4461 - 4463 (2011/09/19)
(R)- and (S)-Lavandulol are important compounds in the cosmetics industry and in pheromone research. We have developed syntheses of (R)- and (S)-lavandulol from (S)- and (R)-limonene, respectively, by microbial Baeyer-Villiger oxidation of the intermediate unsaturated hydroxy ketone. It has been found that the same strain of Acremonium roseum can be successfully used in the key step of the synthesis of both enantiomers of lavandulol.
Selective deoxygenation of allylic alcohol: Stereocontrolled synthesis of lavandulol
Kim, Hee Jin,Su, Liang,Jung, Heejung,Koo, Sangho
supporting information; experimental part, p. 2682 - 2685 (2011/06/26)
Selective deoxygenation of allylic alcohol can be successfully carried out by the formation of alkoxyalkyl ether (EE or MOM), followed by Pd(dppe)Cl 2-catalyzed reduction with LiBHEt3. (+)-S-Lavandulol has been efficiently synthesized by the application of this protocol to the diol derived from the Pb(OAc)4-promoted oxidative ring-opening of (-)-R-carvone. This deoxygenation method is general and selective for allylic alcohols.
Enzymatic transesterification of racemic lavandulol: Preparation of the two enantiomeric alcohols and of the two enantiomers of lavandulyl senecioate
Zada, Anat,Harel, Miriam
, p. 2339 - 2343 (2007/10/03)
(R) and (S)-lavandulol are important compounds in the cosmetics industry and in pheromone research. The senecioyl ester of (S)-lavandulyl has recently been identified as the sex pheromone of the vine mealybug, a significant pest in vineyards. We herein report the preparation of the two enantiomers of lavandulol and lavandulyl senecioate, starting from racemic lavandulol. The preparation is based on a two-cycle enzymatic transesterification of racemic lavandulol with vinyl acetate using Porcine pancreas lipase. High enantioselectivity was achieved while the preparation yielded (R)-lavandulol with 96.7% ee and (S)-lavandulol with 92.6% ee.
Grob-type fragmentation of a carvone derived β-hydroxymesylate: Application to the synthesis of chiral lavandulol derivatives
Mehta, Goverdhan,Karmakar, Swastik,Chattopadhyay, Shital K.
, p. 5013 - 5017 (2007/10/03)
Grob-type fragmentation of the carvone derived diol-monosulphonate 5 has been utilised for the enantioselective synthesis of various lavandulol derivatives
A new synthesis of lavandulol via indium/palladium-mediated umpolung of vinyloxirane
Araki, Shuki,Kambe, Shinya,Kameda, Keiko,Hirashita, Tsunehisa
, p. 751 - 754 (2007/10/03)
A short synthesis of lavandulol is achieved by the In/Pd-mediated reaction of isopropenyloxirane with 3-methylbut-2-enal.
Highly S(N)2'-, (E)-, and antiselective alkylation of allylic phosphates. Facile synthesis of coenzyme Q10
Yanagisawa,Nomura,Noritake,Yamamoto
, p. 1130 - 1136 (2007/10/02)
Treatment of secondary allylic chlorides or allylic phosphates in tetrahydrofuran with prenyl Grignard reagent in the presence of CuCN · 2 LiCl gave geraniol or farnesol derivatives with high S(N)2' selectivity. Phosphate leaving groups were highly transstereoselective for the formation of (E,E)-farnesol derivatives. Furthermore, complete anti-S(N)2' selectivity was observed in the alkylation of optically active allylic phosphates. The present method appears to be an excellent carbon-carbon coupling reaction with high regio-, (E)-, and enantioselectivity. Coenzyme Q10 (ubiquinone 10) was efficiently synthesized using this methodology.
Selective 1,5-Diene Synthesis. A Radical Approach
Yanagisawa, Akira,Noritake, Yoshiyuki,Yamamoto, Hisashi
, p. 1899 - 1902 (2007/10/02)
A new synthetic route to 1,5-dienes is described.Irradiation of a mixture of allyl bromides and allyl sulfides in the presence of hexamethylditin gives the cross-coupled products selectively.
PRENYLATION OF OLEFINS IN NITROMETHANE
Julia, M.,Schmitz, C.
, p. 2485 - 2490 (2007/10/02)
The prenylation of isopentenyl and 3,3-dimethylallyl derivatives could be achieved efficiently with dimethyl vinyl carbinol and a variety of acids in nitromethane.Geraniol and isopentenylacetate led to farnesyl derivatives.
