38651-65-9Relevant articles and documents
Synthesis and antibacterial activity of pinanyl-2-amino pyrimidines
Wu, Jun,Wang, Peng-Na,Xu, Xu,Yang, Yi-Qin,Wang, Shi-Fa
, p. 7769 - 7775 (2014)
A new series of pinene-2-alkyl amino pyrimidines were synthesized from (-)-β-pinene. (+)-No-pinone was obtained from (-)-β-pinene by selective oxidation with potassium permanganate and it was reacted with aromatic aldehydes including benzaldehyde, p-methylbenzaldehyde, p-methoxylbenzaldehyde, p-hydroxybenzaldehyde, p-chlorobenzaldehyde, p-nitrobenzaldehyde, p-fluorobenzaldehyde, o-chlorobenzaldehyde, m-nitrobenzaldehyde, o-vanillin and furfural catalyzed with alkali catalysts to get optically active 3-arylidenenopinones 2a-2l. Then in the alkali catalytic conditions, they were used to synthesize pinanyl-2-amino pyrimidines (3a-3l) with guanidine hydrochloride. The structures of the synthesized compounds were identified by 1H NMR, 13 C NMR, FT-IR, GC-MS and elemental analysis. The antimicrobial activity of the newly synthesized pinanyl-2-amino pyrimidines (3a-3l) was done against C. albicans, A. niger, G. tropicalis, E. coli, S. aureus, B. Subtilis and P. fluorescens. It has been observed that compounds 3a and 3g have strong inhibition effect against Candida albicans, 3g has strong inhibition effect against Aspergillus niger, while 3g also has strong inhibition effect against Candida tropicalis.
The first total synthesis of xenitorins B and C: Assignment of absolute configuration
Chang, Wen-Sheng,Shia, Kak-Shan,Liu, Hsing-Jang,Wei Ly, Tai
, p. 3751 - 3753 (2006)
The first total synthesis of xenitorins B(1) and C(2) in natural form, which serves to confirm the structural assignments, establish the absolute stereochemistry and provide an easy access to the interesting marine sesquiterpenes was analyzed. The synthetic design calls for the use of optically active βpinene(3) both as the the starting substrate and source of chirality and its derivative 4 to facilitate the construction of the core system via a Diels-Alder reaction. This is followed by an acid catalyzed fragmentation process after suitable modifications. Formylation of (+)-7 followed by treatment of the resulting a-hydroxymethylene ketone with hydroxykamine gave rise to isoxazole(-)-9. The identity of the synthetic compounds and the corresponding natural products was established by direct comparison of their H nmr spectra. Result shows that B (-)1 and C(-)2 has been achieved and served to establish the absolute configuration of these structurally interesting natural products.
Sustainable terpene-based polyamides: Via anionic polymerization of a pinene-derived lactam
Winnacker, Malte,Sag, Jacob
, p. 841 - 844 (2018)
A sustainable lactam, which is derived from the renewable terpene β-pinene, is converted to polyamides via a convenient anionic ring-opening polymerization (ROP), which can be easily handled without the use of a costly catalyst. The resulting polyamides have prosperous thermal properties, which enable their future use as high-performance polymers.
Synthesis and crystal structure of chiral (1R,5R)-3-arylidenopinones
Yang, Yi-Qin,Xu, Hai-Jun,Lan, Lan,Wang, Shi-Fa
, p. 7490 - 7494 (2013)
Three (1R,5R)-(-)3-arylideneopinones (2a, 2b and 2c) were first synthesized and characterized by IR, MS, NMR, elemental analysis and single-crystal X-ray diffraction method. The structure indicates that the compound 2a belongs to orthorhombic, space group P212121 with a = 1.0378 (5) nm, b = 1.1156 (6) nm, c = 1.2775 (7) nm, b = 90. V = 1.4791 (13) nm3, Z = 4, r = 1.223 g cm-3, μ = 0.083 mm-1, F (000) = 584 and final R1 = 0.0327, wR2 = 0.0876. The compound 2b belongs to trigonal, space group P32 with a = 0.93024(12) nm, b = 0.93024(12) nm, c = 1.3215(4) nm, b = 90.0. V = 0.9903(3) nm3, Z = 3, r = 1.219 g cm-3, μ = 0.079 mm-1, F(000) = 390 and final R1 = 0.0350, wR2 = 0.0912. The compound 2c belongs to monoclinic, space group P21 with a = 1.20252 (15) nm, b = 0.99228(12) nm, c = 2.3905(3) nm, b = 92.769( 2). V = 2.8491(6) nm3, Z = 8, r = 1.216 g cm-3, μ = 0.254 mm-1, F(000) = 1104 and final R1 =0.0440, wR2 = 0.1069.
Synthesis and study of the antimalarial cardamom peroxide
Hu, Xirui,Lim, Pharath,Fairhurst, Rick M.,Maimone, Thomas J.
, p. 3358 - 3369 (2018)
A full account of our previously disclosed synthesis of the monoterpene dimer cardamom peroxide is reported. Inspired by hypotheses regarding the potential biosynthetic origins of this natural product, several unproductive routes are also reported. The ch
Risk assessment and safety evaluation study for ozonolysis of i-pinene: Raw material of a novel prostaglandin D2 receptor antagonist S-5751
Hida, Takemasa,Kikuchi, Junko,Kakinuma, Makoto,Nogusa, Hideo
, p. 1485 - 1489 (2010)
Safety evaluation for ozonolysis of β-pinene was conducted using DSC, ARC, and RC1e. ARC measurement showed that the concentration of the ozonized mixture affects its thermal stability. The sample at a high concentration of 1.83 mol/L was very unstable even at room temperature and decomposed rapidly. ADT24 of the diluted sample of 0.73 mol/L was 28.2°C. Although reductive decomposition of the ozonized mixture at extremely low temperature is very dangerous because of accumulation of the heat of reaction, its process temperature was validated to not exceed the ADT24. As a result, pilot manufacturing on a 300-L reactor scale could be achieved.
(1R,5S)-(+)-nopinone of high enantiomeric purity
Kozmina, Natasha,Paquette, Leo A.
, p. 2027 - 2030 (1996)
Commercial β-pinene of 87% ee can be upgraded to the 98+% ee level by simple treatment with silver perchlorate. A solid complex is obtained whose formation is more rapid when two like enantiomers are involved. Simple dissolution of this precipitate in water releases the enantio-enriched hydrocarbon from which (+)-nopinone of high enantiomeric purity is obtained via ozonolysis.
One-pot synthesis and antimicrobial evaluation of novel 3-cyanopyridine derivatives of (?)-β-pinene
Liao, Shengliang,Shang, Shibin,Shen, Minggui,Rao, Xiaoping,Si, Hongyan,Song, Jie,Song, Zhanqian
, p. 1512 - 1515 (2016)
A series of novel 3-cyanopyridine derivatives of (?)-β-pinene were designed and synthesized by one-pot four-component domino reactions. The targeted compounds were evaluated for their antimicrobial activity against four bacteria (Klebsiella pneumoniae, Enterobacter aerogenes, Staphylococcus aureus, Staphylococcus epidermidis) and a fungus (Candida albicans). The results showed that most of the minimal inhibitory concentrations (MICs) of these 3-cyanopyridine derivatives against the tested strains was in the range of 15.6–125?mg/L. Among these 3-cyanopyridine derivatives, the MICs of compound 5h against S. epidermidis and C. albicans were 15.6?mg/L, which revealed that compound 5h featured double fluoro substituents at meta- and para-position was the most active compound. In addition, the preliminary structure–activity relationship analysis indicated that the change of substituents on the pyridine ring and benzene ring of 3-cyanopyridine derivatives was an important factor for inducing antimicrobial activity. This research would promote the development of heterocyclic derivatives of β-pinene with antimicrobial activity.
Synthesis and oxidative transformations of new chiral pinane-type γ-ketothiols: Stereochemical features of reactions
Frolova, Larisa L.,Lezina, Olga M.,Rubtsova, Svetlana A.,Subbotina, Svetlana N.,Sudarikov, Denis V.
, (2021/09/06)
Chiral γ-ketothiols, thioacetates, thiobenzoate, disulfides, sulfones, thiosulfonates, and sulfonic acids were obtained from β-pinene for the first time. New compounds open up prospects for the synthesis of other polyfunctional compounds combining a biologically active pinane fragment with various pharmacophore groups. It was shown that the syntheses of sulfanyl and sulfonyl derivatives based on 2-norpinanone are characterized by high stereoselectivity in comparison with similar reactions of pinocarvone. The conditions for the preparation of diastereomerically pure thioacetyl and thiobenzoyl derivatives based on pinocarvone, as well as for the chemoselective oxidation of γ-ketothiols with chlorine dioxide to the corresponding thiolsulfonates and sulfonic acids, were selected. The effect of the VO(acac)2 catalyst on the increase in the yields of thiosulfonates was shown. A new direction of the transformation of thiosulfonates with the formation of sulfones was revealed. In the case of pinocarvone-based sulfones, the configuration is inversed at the C2 atom. An epimerization scheme is proposed.
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.
