105-87-3Relevant articles and documents
Facile syntheses of [8,9-2H2]- and [8-2H]-digeranyl
Nakagawa, Osamu,Shimoda, Kei,Izumi, Shunsuke,Hirata, Toshifumi
, p. 1301 - 1309 (2000)
[8,9-2H2]- and [8-2H]-(2E,6E,10E,14E)-2,6,11,15-tetramethyl-2,6,10,14-hexadecatetraene (digeranyl) (1 and 2) have been synthesized from geraniol by the condensation of geranyl p-tolylsulfone and reductive desulfonylation in the key steps.
Vakuum UV Photolyses of Some Bichromophoric Alkenes Possesing Hydroxyl or Methoxycarbonyl Group
Inoue, Yoshihisa,Goan, Kazuyoshi,Hakushi, Tadao
, p. 2217 - 2220 (1985)
The direct photolyses at 185 nm of some naturally occuring and related bichromophoric alkenes possesing hydroxyl or methoxycarbonyl group at an allylic, homoallylic, or remote position gave the geometrical isomers as the major photoproducts detectable on gas chromatography.The isomerization yield was highly sensitive to the functional group introduced and its position; allylic alkenols gave poor yields, while both functionalization at a remote position and esterification of the hydroxyl group improve the photoisomerization yield.
Alcoholyses and acetolyses of allylic and tertiary benzylic alcohols catalyzed by 2,3-dichloro-5,6-dicyanobenzoquinone
Iranpoor,Mottaghinejad
, p. 2253 - 2260 (1995)
Allylic and tertiary benzylic alcohols can be converted into their corresponding ethers and acetates selectively and efficiently in the presence of catalytic amounts of 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ).
The aphid sex pheromone cyclopentanoids: Synthesis in the elucidation of structure and biosynthetic pathways
Dawson, Glenn W.,Pickett, John A.,Smiley, Diane W. M.
, p. 351 - 361 (1996)
Identification of a range of aphid sex pheromones as comprising the cyclopentanoids (4aS,7S,7aR)-nepetalactone, (1R,4aS,7S,7aR)-nepetalactol and the (1S)- and (1R,4aR,7S,7aS)-nepetalactols required samples authenticated by 1H and 13C NMR. These and related compounds were provided by small scale synthesis and extraction from plants in the genus Nepeta (Lamiaceae). The subsequent discovery that the synthetic sex pheromones could attract males, and also parasitic wasps that attack aphids, has created a need for large scale syntheses of the cyclopentanoids. This is afforded by cyclisation of the 8-oxo-1-enamine of citronellal as originally developed by Schreiber and co-workers (1986). Investigation into the biosynthesis of the cyclopentanoids by plants for exploiting aphid sex pheromones in crop protection by means of molecular biology required synthesis of putative biosynthetic intermediates, some with radioactive isotopic labelling, particularly 8-oxidised monoterpene alcohols and aldehydes.
Photoacylation of alcohols in neutral medium
Debieux, Jean-Luc,Cosandey, Anne,Helgen, Celine,Bochet, Christian G.
, p. 2073 - 2077 (2007)
We report here conditions which allow the photoacylation of primary, secondary and tertiary alcohols with N-acetyl-5,7-dinitroindoline under exceptionally mild conditions, at wavelengths harmless to most functional groups, including otherwise photosensitive ones. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Synthesis of monoterpene esters by alcoholysis reaction with Mucor miehei lipase in a solvent-free system
Chatterjee,Bhattacharyya
, p. 651 - 655 (1998)
The syntheses of geranyl acetate and citronellyl acetate by alcoholysis reaction catalyzed by immobilized lipase from Mucor miehei was studied for the first time in a solvent-free system. Reactions were carried out at a terpene alcohol/acyl donor molar ratio of 1:5 with Lipozyme at 10% of the total weight of the reactants in a solvent-free system. Incubations were carried out at 55 to 60 °C for ethyl and butyl acetates as acyl donors, whereas for methyl acetate the incubation temperature was 40 to 45 °C. Excess concentration of acyl donor increases the percentage of geranyl acetate and citronellyl acetate, while excess of terpene alcohol concentration decreases the same. Yields from 75 to 77% molar conversion (90 to 98% conversion, w/w) were obtained after 8 to 28 h of reaction time.
Synthetic applications of homoiodo allylsilane II. Total syntheses of (-)-andrographolide and (+)-rostratone
Gao, Hai-Tao,Wang, Bian-Lin,Li, Wei-Dong Z.
, p. 9436 - 9448 (2014)
The first total synthesis of (-)-andrographolide (1), an ent-Labdane diterpenoid lactone from Asian medicinal herb Andrographis paniculata, was achieved via the biomimetic cyclization of an epoxy homoiodo allylsilane precursor 7. Asymmetric total synthesis of (+)-rostratone (25), an antipodal Labdane diterpenoid, was also accomplished via similar biomimetic cyclization of a readily accessible epoxy homoiodo allylsilane precursor 18.
A simple method for the removal of organotin residues from acetates and a homoallylic alcohol prepared from organostannane reagents: Column chromatography using 10%-moist SiO2
Nishida, Takanori,Matsuda, Daiki,Kasuga, Issei,Orita, Akihiro,Otera, Junzo
, p. 1280 - 1282 (2016)
Simple column chromatography using 10%-moist silica gel enabled efficient removal of organotin residues from geranyl acetate, which was prepared by the acetylation of geraniol with vinyl acetate in the presence of a catalytic amount of a 1,3-dichloro-substituted tetrabutyldistannoxane. The desired acetate contained only 2.4 ppm of organotin residues. In sharp contrast to this, a similar purification method using dry silica as the stationary phase provided acetate containing ca. 5000 ppm of organotin residues.
Continuous-Flow Chemo and Enzymatic Synthesis of Monoterpenic Esters with Integrated Purification
Adarme, Carlos A.A.,Le?o, Raquel A.C.,de Souza, Stefania P.,Itabaiana, Ivaldo,de Souza, Rodrigo O.M.A.,Rezende, Claudia M.
, p. 39 - 46 (2018)
Monoterpenic esters are very important flavor and fragrance compounds due to their organoleptic properties. Despite their importance, many drawbacks are found for the production of monoterpenic esters. Here in we report two different approach's (chemo and enzymatic) for the continuous production of monoterpenic esters with integrated purification arriving on the desired molecules with high yields (>95%) and short reaction times.
Efficient synthesis and biological evaluation of ω-oxygenated analogues of vitamin K2: Study of modification and structure-activity relationship of vitamin K2 metabolites
Suhara, Yoshitomo,Murakami, Aya,Kamao, Maya,Mimatsu, Shino,Nakagawa, Kimie,Tsugawa, Naoko,Okano, Toshio
, p. 1622 - 1625 (2007)
Novel ω-oxygenated vitamin K2 analogues, which are candidates for metabolites of vitamin K2 homologues, were efficiently synthesized and their apoptosis-inducing activity was evaluated. We revealed that some of those analogues were biologically active and the side-chain part played an important role in apoptosis-inducing activity. Our results can provide useful information to develop the structure-activity relationship of vitamin K2 analogues for new drugs based on vitamin K.
