74281-22-4Relevant academic research and scientific papers
One-Pot Ozonolytic Synthesis of Isoniazid Derivatives from (–)-α-Pinene and Δ3-Carene
Legostaeva, Yu. V.,Garifullina,Nazarov,Ishmuratov, G. Yu.
, p. 146 - 148 (2018)
Optically active isoniazid derivatives containing a cyclopropane or cyclobutane fragment have been synthesized by ozonolysis of (+)-Δ3-carene and (–)-α-pinene, followed by treatment of the ozonolysis products with isonicotinic acid hydrazide.
Compounds combining aminoadamantane and monoterpene moieties: Cytotoxicity and mutagenic effects
Suslov, Evgeniy V.,Ponomarev, Konstantin Yu.,Rogachev, Artem D.,Pokrovsky, Michail A.,Pokrovsky, Andrey G.,Pykhtina, Maria B.,Beklemishev, Anatoly B.,Korchagina, Dina V.,Volcho, Konstantin P.,Salakhutdinov, Nariman F.
, p. 629 - 635 (2015)
A series of secondary amines combining monoterpenoid and aminoadamantane moieties have been synthesized. Their cytotoxic activity against human cancer cells CEM-13, MT-4, and U-937 has been studied for the first time. Most of the obtained compounds exhibited a significant cytotoxic activity with the median cytotoxic dose (CTD50) ranging from 6 to 84 μM. The most promising results were obtained for compound 2b which was synthesized from 1-aminoadamantane and (-)-myrtenal and revealed a high activity against all tumor lines used (CTD50= 12/21 μM) along with low toxicity with respect to MDCK cells (CTD50= 1500 μM). The synthesized amines do not exert the genotoxic effect on cells of the biosensor strain based on recombinant E. coli cells bearing the pRAC-gfp plasmid.
Surfactant-Assisted Ozonolysis of Alkenes in Water: Mitigation of Frothing Using Coolade as a Low-Foaming Surfactant
Buntasana, Supanat,Hayashi, Jun,Klumphu, Piyatida,Padungros, Panuwat,Saetung, Prakorn,Vilaivan, Tirayut
supporting information, (2022/02/23)
Aqueous-phase ozonolysis in the atmosphere is an important process during cloud and fog formation. Water in the atmosphere acts as both a reaction medium and a reductant during the ozonolysis. Inspired by the atmospheric aqueous-phase ozonolysis, we herein report the ozonolysis of alkenes in water assisted by surfactants. Several types of surfactants, including anionic, cationic, and nonionic surfactants, were investigated. Although most surfactants enhanced the solubility of alkenes in water, they also generated excessive foaming during the ozone bubbling, which led to the loss of products. Mitigation of the frothing was accomplished by using Coolade as a nonionic and low-foaming surfactant. Coolade-assisted ozonolysis of alkenes in water provided the desired carbonyl products in good yields and comparable to those achieved in organic solvents. During the ozonolysis reaction, water molecules trapped within the polyethylene glycol region of Coolade were proposed to intercept the Criegee intermediate to provide a hydroxy hydroperoxide intermediate. Decomposition of the hydroxy hydroperoxide led to formation of the carbonyl product without the need for a reductant typically required for the conventional ozonolysis using organic solvents. This study presents Coolade as an effective surfactant to improve the solubility of alkenes while mitigating frothing during the ozonolysis in water.
Molecular Chirality and Cloud Activation Potentials of Dimeric α-Pinene Oxidation Products
Bé, Ariana Gray,Bellcross, Aleia,Geiger, Franz M.,Thomson, Regan J.
, p. 16653 - 16662 (2021/10/20)
The surface activity of ten atmospherically relevant α-pinene-derived dimers having varying terminal functional groups and backbone stereochemistry is reported. We find ～10% differences in surface activity between diastereomers of the same dimer, demonstrating that surface activity depends upon backbone stereochemistry. Octanol-water (KOW) and octanol-ammonium sulfate partitioning coefficient (KOAS) measurements of our standards align well with the surface activity measurements, with the more surface-active dimers exhibiting increased hydrophobicity. Our findings establish a link between molecular chirality and cloud activation potential of secondary organic aerosol particles. Given the diurnal variations in enantiomeric excess of biogenic emissions, possible contributions of such a link to biosphere:atmosphere feedbacks as well as aerosol particle viscosity and phase separation are discussed.
Nickel-Catalyzed Selective Reduction of Carboxylic Acids to Aldehydes
Iosub, Andrei V.,Morav?ík, ?tefan,Wallentin, Carl-Johan,Bergman, Joakim
supporting information, p. 7804 - 7808 (2019/10/14)
The direct reduction of carboxylic acids to aldehydes is a fundamental transformation in organic synthesis. The combination of an air-stable Ni precatalyst, dimethyl dicarbonate as an activator, and silane reductant effects this reduction for a wide variety of substrates, including pharmaceutically relevant structures, in good yields and with no overreduction to alcohols. Moreover, this methodology is scalable, allows access to deuterated aldehydes, and is also compatible with one-pot utilization of the aldehyde products.
Synthesis and Inhibitory Properties of Imines Containing Monoterpenoid and Adamantane Fragments Against DNA Repair Enzyme Tyrosyl-DNA Phosphodiesterase 1 (Tdp1)
Zakharenko,Mozhaitsev,Suslov,Korchagina,Volcho,Salakhutdinov,Lavrik
, p. 672 - 676 (2018/08/03)
Six imines including four new ones were synthesized via the reaction of monoterpenoid aldehydes with aminoadamantanes. The inhibitory activities of the synthesized compounds against purified human recombinant DNA repair enzyme tyrosyl-DNA phosphodiesterase 1 (Tdp1) fell in the range IC50 = 5.5–7.1 μM.
Convenient synthesis of non-conjugated alkynyl ketones from keto aldehydes by a chemoselective one-pot nonaflation - Base catalyzed elimination sequence
Boltukhina, Ekaterina V.,Sheshenev, Andrey E.,Lyapkalo, Ilya M.
experimental part, p. 5382 - 5388 (2011/08/06)
Keto aldehydes were selectively converted to non-conjugated alkynyl ketones possessing an unsubstituted alkyne terminus using one-pot nonaflation - base catalyzed elimination reaction sequences. Consecutive one-pot nonaflation of keto aldehydes with perfluorobutane-1-sulfonyl fluoride and elimination of the nonaflyl group using the P1 phosphazene base resulted in the formation of a terminal CC triple bond with the keto group remaining intact. Careful optimization of the reaction conditions enabled a highly chemoselective conversion of the aldehyde function in the presence of unprotected keto groups exploiting a minor difference in acidity of their α-hydrogen atoms. Scope and limitations of the protocol as well as possible implementation of these substrates in Sonogashira coupling were explored.
Synthesis of 13C1-pinonaldehyde
Dicus, Christopher W.,Willenbring, Dan,Nantz, Michael H.
, p. 223 - 229 (2007/10/03)
13C1-pinonaldehyde is prepared in seven steps from cis-pinonic acid. In the key sequence, the introduction of labeled carbon is accomplished by Lieben degradation of a methyl ketone followed by treatment of the resultant carboxylic a
Highly chemoselective reduction of aldehyde function catalyzed by polymer-bound Rh6 cluster complex under water-gas shift reaction conditions
Mizugaki, Tomoo,Ebitani, Kohki,Kaneda, Kiyotomi
, p. 3005 - 3008 (2007/10/03)
A functionalized polymer-bound Rh6 cluster complex showed high catalytic activity for chemoselective reduction of aldehydes in the presence of CO and H2O. The reaction system consists of the triphase, which makes work-up procedure simple.
Ruthenium Tetroxide Oxidation of Alkenes. A More Complete Picture
Albarella, Laura,Piccialli, Vincenzo,Sica, Donato,Smaldone, Dina
, p. 2442 - 2456 (2007/10/03)
The ruthenium tetroxide oxidation of some linear and cyclic alkenes, representatives of five substitution patterns, has been performed in acetone-water (5:1) solution at -70 deg C using stoichiometric ammounts of the oxidant.The main reaction products are 1,2-diols and/or α-ketols depending on the nature of the substrate little amounts of scission products, aldehydes and/or carboxylic acids, are also obtained.Generally 1,2-diols predominate over α-ketols except in the oxidation of (-)-α-pinene that afforded the α-ketol in 51percent yield while no trace of the corresponding 1,2-diol was detected.All reactions prceeded through the formation of unstable brownish precipitates, presumably the intermediate ruthenium (VI) esters, which easily decomposed during the work-up step.Results from oxidation of trans-7-tetradecene and cis and trans-11-tetradecenyl acetate indicated that the reaction was syn stereospecific.In some cases, 1,3-dioxolane products, formed by condensation of the 1,2-diol and the aldehyde materials, were also obtained among the reaction products.Their possible origin is briefly discussed.
