14505-74-9Relevant academic research and scientific papers
Synthesis method of alpha-cyclocitral
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Paragraph 0021; 0050; 0051, (2018/06/26)
The invention discloses a synthesis method of alpha-cyclocitral. The method comprises the steps of (1) carrying out Diels-Alder reaction on 1,3-pentadiene and methylcrotonaldehyde under the catalysisof lewis acid to obtain a 2,6,6-trimethyl-3-cyclohexenyl formaldehyde crude product; (2) carrying out isomerization reaction on the 2,6,6-trimethyl-3-cyclohexenyl formaldehyde crude product obtained in step (1) under the catalysis of a catalyzer to generate an alpha-cyclocitral crude product. The method provided by the invention is easy to get reaction raw materials, mild in conditions, easy to control, free of generating byproducts, simple in process, favorable in industrial production, green and environmentally friendly.
Method for preparing cyclocitral by micro-structural reactors
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, (2017/02/09)
The invention discloses a method for preparing cyclocitral by micro-structural reactors. The method comprises steps as follows: a liquid raw material citral and organic amine in a mole ratio being 1: (0.8-1.5) are simultaneously pumped into a tubular reactor or one micro-structural reactor for an amination reaction, the reaction temperature of the reactor is controlled in a range of 10-20 DEG C, a flow velocity of a reaction liquid is controlled, the reaction liquid is enabled to totally stay in the reactor for 0.1-25 min, and obtained aldimine and concentrated sulfuric acid are injected into another micro-structural reactor and subjected to a ring closing reaction; a reaction product is neutralized by a sodium hydroxide solution and is subjected to acidic hydrolysis, liquid separation, reduced pressure distillation and drying, and a pale yellow oily product, namely, cyclocitral, is obtained. According to the method, the reaction time is short, the reaction temperature is accurate and controllable, and product selectivity and yield are high. The method adopts simple steps, and is convenient to operate and high in practicability.
Synthesis of three putative kairomones of the beech leaf-mining weevil Orchestes fagi (L.)
Mayo,Silk,Abeysekera,MaGee
supporting information, p. 1124 - 1132 (2016/07/21)
The beech leaf-mining weevil, Orchestes fagi (L.), also known as the beech flea weevil, is a common and widespread pest of beech, Fagus sylvatica L., in its native Europe. It now appears to be well established in Nova Scotia, Canada. We report a novel synthesis of 9-geranyl-p-cymene and syntheses of 9-geranyl-α-terpinene and 1,1-dimethyl-3-methylene-2-vinylcyclohexane, making partial use of known methods. All three of these compounds are found in beech leaf volatiles and/or wood and are putative kairomones of the beech leaf-mining weevil.
Nitriles and carbonyl groups as acceptors in titanocene-catalyzed radical cyclizations
Gansaeuer, Andreas,Piestert, Frederik,Huth, Inga,Lauterbach, Thorsten
scheme or table, p. 3509 - 3515 (2009/05/26)
A catalytic approach to the titanocene-mediated radical cyclization of epoxy nitriles and epoxy carbonyl compounds to hydroxy ketones and diols is described. The reaction is sensitive to the substitution pattern of the catalyst and especially useful for the preparation of cyclobutanones. It can also be used for nitrile group transfer. Georg Thieme Verlag Stuttgart.
Improved synthesis of methyl 3-oxo-2,6,6-trimethylcyclohex-1-ene-1- carboxylate, an A-ring intermediate for (±)strigol
Qianchao,Shiqing, Pi,Xinzhi, Chen
, p. 494 - 496 (2008/09/21)
Methyl 3-oxo-2,6,6-trimethylcyclohex-1-ene-1-carboxylate was synthesised over eight steps from the starting material of citral instead of α-ionone. KMnO4, HC(OEt)3 and O2/TEMPO/CuCl were substituted for NaIO4, CH3I and pyridinium chlorochromate, respectively. Every step was simplified and gave a 48% overall yield. The procedure is suitable for large scale production.
Isolation, synthesis, and anti-tumor activities of a novel class of podocarpic diterpenes
Xiong, Yi,Wang, Kuiwu,Pan, Yuanjiang,Sun, Hongxiang,Tu, Jue
, p. 786 - 789 (2007/10/03)
A novel unusual 17-carbon diterpenoid, named (+)-7-deoxynimbidiol, was isolated from the stalks of Celastrus hypoleucus (Oliv.) Warb. Its racemate and derivatives were synthesized, and the inhibitory activities of these compounds against four cultured human-tumor cell lines were evaluated. The structure-activity relationship was discussed.
A simple and efficient highly enantioselective synthesis of α-ionone and α-damascone
Bovolenta, Marcella,Castronovo, Francesca,Vadala, Alessandro,Zanoni, Giuseppe,Vidari, Giovanni
, p. 8959 - 8962 (2007/10/03)
An efficient highly enantioselective (ee ≥99%) synthesis of α-ionone and α-damascone is described. Both enantiomers of title compounds were synthesized through two straightforward pathways diverging from enantiopure (R)- or (S)-α-cyclogeraniol. These versatile building blocks were obtained by regioselective ZrCl4-promoted biomimetic cyclization of (6S)- or (6E)-(Z)-6,7-epoxygeraniol, respectively, followed by deoxygenation of the so formed secondary alcohol. The chiral information was encoded by a highly regioselecive Sharpless asymmetric dihydroxylation of inexpensive geranyl acetate.
Synthesis of olivacene, a constituent of Archilejeunea olivacea
Kamat, Shrivallabh P.,D'Souza, Asha M.,Paknikar, Shashikumar K.
, p. 2662 - 2664 (2007/10/03)
A simple synthesis of olivacene 1, a naturally occurring sesquiterpenoid hydrocarbon isolated from Archilejeunea olivacea has been described.
Stereoselective synthesis of (+)-ferruginyl methyl ether and (+)-sugiyl methyl ether
Yonghong, Gan,Xinfu, Pan
, p. 130 - 132 (2007/10/03)
A facile stereoselective synthetic procedure to (+)-ferruginyl methyl ether and (+)-sugiyl methyl ether has been developed with high stereoselectivity and overall yield.
Stereoselective synthesis of (-)-6,7-dehydroferruginyl methyl ether
Gan, Yonghong,Li, Anpai,Pan, Xinfu,Chan, Albert S. C.,Yang, Teng-Kuei
, p. 781 - 787 (2007/10/03)
A stereoselective synthetic route to (-)-6,7-dehydroferruginyl methyl ether was developed from (S)-(-)-α-cyclocitral. Copyright (C) 2000 Elsevier Science Ltd.
