58041-00-2Relevant academic research and scientific papers
Montmorillonite K 10 (clay) catalyzed hydrolysis of aryl-substituted α,β-difluoroallyl alcohols leading to (Z)-α-fluoro-β-aryl-substituted acrylaldehydes
Funabiki, Kazumasa,Murata, Eiji,Fukushima, Yoshitaka,Matsui, Masaki,Shibata, Katsuyoshi
, p. 4637 - 4642 (1999)
Aryl-substituted aα,β-difluoroallyl alcohols 1 were readily hydrolyzed in the presence of a catalytic amount of montmorillonite K 10 (clay) in hexane at reflux temperature for 1 h to give the corresponding (Z)-α- fluoro-β-aryl-substituted acrylaldehydes 2
Reaction of β-fluorinated vinamidinium salts with Grignard reagents and reducing agents - New facile and efficient route to fluorinated allylamines
Yamanaka,Odani,Ishihara,Konno,Gupton
, p. 199 - 205 (2001)
β-Fluorinated vinamidinium salts (1) readily reacted with a series of Grignard reagents in tetrahydrofuran, followed by the action of reducing agents at room temperature, to produce stereospecifically the corresponding fluorinated allylamines (4 and 5) in good to excellent yields.
Cis-cinnamic acid analogue, gravitropism modifier (by machine translation)
-
, (2019/11/30)
[Problem] cinnamic acid or cinnamic acid analogue comprising adjusting agent gravitropism cis. [Solution] cinnamic acid and/or cinnamic acid as an active ingredient to adjust gravitropism cis edge agents, cinnamic acid edge is, for example obtained by reacting compounds of the following formula. (In the formula, R is a phenyl group. )Figure 6 [drawing] (by machine translation)
Effect of Fluorination on Skin Sensitization Potential and Fragrant Properties of Cinnamyl Compounds
Charpentier, Julie,Emter, Roger,Koch, Heinz,Lelièvre, Dominique,Pannecoucke, Xavier,Couve-Bonnaire, Samuel,Natsch, Andreas,Bombrun, Agnes
, (2018/04/27)
A series of three α- and three β-fluorinated representatives of the family of cinnamate-derived odorants (cinnamaldehyde (1), cinnamyl alcohol (2), and ethyl cinnamate (3)) as used as fragrance ingredients is described. Olfactive evaluation shows that the
One-Pot l-Proline-Mediated Stereoselective α-C(sp2)–H Fluorination of α,β-Unsaturated Aldehydes through Methoxyfluorination–Elimination
Zhou, Jiadi,Jiang, Xinpeng,Jin, Can,Guo, Zhicheng,Su, Bin,Su, Weike
, p. 3631 - 3634 (2017/07/22)
A one-pot, two-step l-proline-mediated stereoselective α-C(sp2)–H fluorination of α,β-unsaturated aldehydes towards their corresponding (Z)-α-fluoro-α,β-unsaturated aldehydes has been developed. The first step utilises Selectfluor as a fluorinating agent in CH3NO2/MeOH forming (Z)-α-fluoro-α,β-unsaturated aldehydes and their corresponding dimethyl acetals through methoxyfluorination-elimination. In the second step, water is added to promote the hydrolytic cleavage of the dimethyl acetals. The obtained (Z)-α-fluoro-α,β-unsaturated aldehydes were smoothly reduced to the corresponding alcohols by using NaBH4.
Copper-catalyzed ligand free ring-opening amination of gem-fluorohalocyclopropanes – An efficient route toward 2-fluoroallylamines
Novikov, Maxim A.,Ibatov, Yaroslav A.,Volchkov, Nikolai V.,Lipkind, Maria B.,Semenov, Sergei E.,Nefedov, Oleg M.
, p. 58 - 72 (2017/01/18)
Ring-opening amination of gem-chlorofluoro- and gem-bromofluorocyclopropanes with secondary alkyl, aryl amines or hydroxylamines catalyzed by copper(I) or copper(II) compounds with no additional ligands affords tertiary 2-fluoroallylamines or hydroxylamines in moderate to excellent yields. The reaction pathway involves isomerization of gem-fluorohalocyclopropanes to 2-fluoroallyl halides followed by in situ nucleophilic substitution of a halide by an N-nucleophile. The p-methoxyphenyl (PMP) protective group is efficient in the preparation of secondary 2-fluoroallylamines by this method. Primary 2-fluoroallylamines can only be obtained by a stepwise protocol including CuX-catalyzed isomerization of gem-fluorohalocyclopropanes to 2-fluoroallylic halides followed by amination.
CIS CINNAMIC ACID ANALOG AND GRAVITROPISM MODIFIER
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, (2017/06/02)
PROBLEM TO BE SOLVED: To provide a gravitropism modifier having effects on creeping property of plants or sugar content of fruits. SOLUTION: There is provided a gravitropism modifier containing cis cinnamic acid and/or a cinnamic acid analog represented by the formula (1) as active ingredients. (1), where A is cyclic hydrocarbon which may have a substituent, X is a bound or a C1 to 5 substituted or unsubstituted hydrocarbon chain, R1 is H, a hydroxyl group, an alkali earth metal salt or the like, R2 is a bond or a C1 to 5 substituted or unsubstituted hydrocarbon chain and R3 and R4 are H or together form C5 to 8 cyclic hydrocarbon. SELECTED DRAWING: Figure 6 COPYRIGHT: (C)2016,JPOandINPIT
A new approach to the synthesis of (Z)-2-fluoro-2-alkenals via Wittig-type carbonyl condensation reactions of 2-(fluoromethyl)-4,4,6-trimethyl-1,3-oxazine phosphonium bromide
Kajjout, Mohammed,Smietana, Micha?l,Leroy, Jacques,Rolando, Christian
, p. 1658 - 1660 (2013/03/29)
We report here the transformation of aldehydes to their (Z)-α-fluoro-α,β-unsaturated aldehyde homologs by condensation with the phosphonium salt of the Meyer's oxazine obtained from bromofluoroacetonitrile. After methylation with trimethyloxonium tetrafluoroborate the quaternized oxazine is cleanly reduced to mostly Z 2-fluoro-2-alkenals by sodium borohydride at room temperature. This methodology is compatible with usual protecting groups and affords an efficient access to functionalized mostly Z 2-fluoro-2-alkenals derived from natural products and their corresponding (Z)-2-fluoro-2-alkenols.
Palladium-Catalyzed Stereoconvergent Formylation of (E/Z)-β-Bromo- β-fluorostyrenes: Straightforward Access to (Z)-α-Fluorocinnamic Aldehydes and (Z)-β-Fluorocinnamic Alcohols
Zemmouri, Rajae,Kajjout, Mohammed,Castanet, Yves,Eddarir, Said,Rolando, Christian
experimental part, p. 7691 - 7698 (2011/12/02)
We report here the stereoconvergent formylation of (E/Z)-β-bromo- β-fluorostyrene mixtures with carbon monoxide and sodium formate catalyzed by palladium. Optimization of reaction conditions leads to the corresponding pure (Z)-α-fluorocinnamaldehydes in g
The first synthesis and reaction of β-ethoxy-α-fluoro-α- (phenylselanyl)ethene: Scandium or lanthanum triflate catalyzed α-fluoroformylalkenylation of aldehydes
Hatanaka, Fuminori,Tsuchiya, Miyuki,Yoshimatsu, Mitsuhiro
, p. 2191 - 2194 (2007/10/03)
We describe the first preparation of the hitherto unknown β-ethoxy-α-fluoro-α-(phenylselanyl)ethenes and the successful Lewis acid catalyzed α-fluoroformylalkenylation of non-enolizable aldehyde acetals to provide α,β-unsaturated aldehydes or acetals excl
