71628-89-2

Upstream product

• 129222-66-8 C₆H₇(CH₂)(OOSn(C₄H₉)3)(C(CH₃)2) 
• 80-56-8 rac-α-pinene 
• 80-56-8 Pinene 
• 17879-35-5 cis-pinonic acid 
• 22630-96-2 1-(2-Hydroxyethyl)-3-(1-hydroxyethyl)-2,2-dimethylcyclobutane 
• 71582-32-6 1-((1S,3S)-3-(2,2-dimethoxyethyl)-2,2-dimethylcyclobutyl)ethan-1-one 
• 21803-49-6 (1S,2S,3R,5S)-(+)-pinanediol 
• 18680-27-8 pinanediol 
• 7785-70-8 (+)-α-pinene 

Downstream Products

• 177316-73-3 1-((1S)-2,2,3c-trimethyl-cyclobut-r-yl)-ethanone 
• 132478-08-1 cis-pinononic aldehyde 
• 22571-78-4 (+)-cis-pinononoic acid 
• 28465-10-3 (+)-(1R)-cis-2,2-dimethyl-3-isopropenylcyclobutanemethanol acetate 
• 92469-61-9 6-(2,2,3-trimethyl-cyclobutyl)-hepta-3,5-dien-2-one 
• 2704-79-2 1-(2,2,3-trimethyl-cyclobutyl)-ethanone 

Relevant academic research and scientific papers

Synthesis and Inhibitory Properties of Imines Containing Monoterpenoid and Adamantane Fragments Against DNA Repair Enzyme Tyrosyl-DNA Phosphodiesterase 1 (Tdp1)

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.

Rate coefficients for the OH + pinonaldehyde (C10H 16O2) reaction between 297 and 374 K

The rate coefficient for the reaction of OH with pinonaldehyde (C 10H16O2, 3-acetyl-2,2-dimethyl-cyclobutyl- ethanal), a product of the atmospheric oxidation of α-pinene, was measured under pseudo-first-order conditions in OH at temperatures between 297 and 374 K at 55 and 96 Torr (He). Laser induced fluorescence (LIF) was used to monitor OH in the presence of pinonaldehyde following its production by 248 nm pulsed laser photolysis of H2O2. The reaction exhibits a negative temperature dependence with an Arrhenius expression of k1(T) = (4.5 ± 1.3) × 10-12 exp((600 ± 100)/7) cm3 molecule-1 s-1; K1(297 K) = (3.46 ± 0.4) × 10-11 cm3 molecule-1 s-1. There was no observed dependence of the rate coefficient on pressure. Our results are compared with previous relative rate determinations of k1 near 297 K and the discrepancies are discussed. The state of knowledge for the atmospheric processing of pinonaldehyde is reviewed, and its role as a marker for α-pinene (monoterpene) chemistry in the atmosphere is discussed.

Surfactant-Assisted Ozonolysis of Alkenes in Water: Mitigation of Frothing Using Coolade as a Low-Foaming Surfactant

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

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.

Dibismuthanes in catalysis: From synthesis and characterization to redox behavior towards oxidative cleavage of 1,2-diols

A family of aryl dinuclear bismuthane complexes has been successfully synthesized and characterized. The two bismuth centers are bonded to various xanthene-type backbones, which differ in ring-size and flexibility, resulting in complexes with different intramolecular Bi?Bi distances. Moreover, their pentavalent Bi(v) analogues have also been prepared and structurally characterized. Finally, the synergy between bismuth centers in catalysis has been studied by applying dinuclear bismuthanes5-8to the catalytic oxidative cleavage of 1,2-diols. Unfortunately, no synergistic effects were observed and the catalytic activities of dinuclear bismuthanes and triphenylbismuth are comparable.

1,2-Amino Alcohols via Cr/Photoredox Dual-Catalyzed Addition of α-Amino Carbanion Equivalents to Carbonyls

Herein, we report the synthesis of protected 1,2-amino alcohols starting from carbonyl compounds and α-silyl amines. The reaction is enabled by a Cr/photoredox dual catalytic system that allows the in situ generation of α-amino carbanion equivalents which act as nucleophiles. The unique nature of this reaction was demonstrated through the aminoalkylation of ketones and an acyl silane, classes of electrophiles that were previously unreactive toward addition of alkyl-Cr reagents. Overall, this reaction broadens the scope of Cr-mediated carbonyl alkylations and discloses an underexplored retrosynthetic strategy for the synthesis of 1,2-amino alcohols.

Nickel-Catalyzed Selective Reduction of Carboxylic Acids to Aldehydes

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.

Sodium Hypochlorite Pentahydrate as a Reagent for the Cleavage of trans-Cyclic Glycols

Sodium hypochlorite pentahydrate (NaOCl·5H2O) can be used toward the efficient glycol cleavage of trans-cyclic glycols, which are generally resistant to this transformation. Interestingly, the reaction of cis-cyclic glycols with NaOCl·5H2O is slower than that observed for the corresponding trans-isomer. This trans selectivity is in sharp contrast to traditional oxidants used for glycol cleavage. Acyclic glycols can also react efficiently with NaOCl·5H2O to form their corresponding carbonyl compounds in high yield.

Efficient Vanadium-Catalyzed Aerobic C?C Bond Oxidative Cleavage of Vicinal Diols

The aerobic oxidative C?C bond cleavage of vicinal diols catalyzed by vanadium amino triphenolates is described. Our results show that C?C bond cleavage can be performed in different solvents, under an air or oxygen atmosphere, with a large variety of glycols (cyclic or linear, with aromatic or aliphatic substituents) affording the corresponding carbonyl derivatives with high chemoselectivity. Reactions can be performed with as little as 10 ppm of catalyst reaching TON up to 81,000 and TOFs of up to 4150 h?1. A reaction mechanism, rationalized by density functional theory calculations, is also proposed. (Figure presented.).

Synthesis of 13C1-pinonaldehyde

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