24903-95-5

Usage

Uses

Used in the Food Industry:
6,6-Dimethylbicyclo[3.1.1]heptan-2-one is used as a flavoring agent to impart a pleasant and fruity aroma to a variety of food products, enhancing their sensory appeal to consumers.
Used in the Fragrance and Cosmetics Industry:
In the production of fragrances, perfumes, and other cosmetic products, 6,6-dimethylbicyclo[3.1.1]heptan-2-one serves as a key ingredient due to its attractive scent, contributing to the overall olfactory profile of these products.
Used in Pharmaceutical Synthesis:
6,6-Dimethylbicyclo[3.1.1]heptan-2-one is utilized in the synthesis of pharmaceuticals, where its stable and rigid structure aids in the development of new medicinal compounds.
Used as an Intermediate in Organic Chemistry Reactions:
6,6-dimethylbicyclo[3.1.1]heptan-2-one also plays a crucial role as an intermediate in various organic chemistry reactions, facilitating the formation of complex chemical entities for diverse applications.

Upstream product

• 79720-58-4 4-Isopropyl-7-tosyloxycyclohexanone 
• 28664-03-1 (3-ethoxycarbonyl-2,2-dimethyl-cyclobutyl)-acetic acid ethyl ester 
• 177698-19-0 Beta-pinene 
• 7732-18-5 water 
• 18172-67-3 beta-pinene 
• 60-29-7 diethyl ether 
• 7664-93-9 sulfuric acid 
• 471-83-0 nopinic acid 
• 127-91-3 (1R,5R)-(+)-β-pinene 
• 28664-02-0 pinic acid 
• 487-51-4 4-carbethoxy-3-methyl-2-cyclohexen-1-one 
• 18172-67-3 (?)-β-pinene 
• 473-72-3 pinonic acid 
• 79720-57-3 4-(1-hydroxy-1-methylethyl)cyclohexanone ethylene ketal 

Downstream Products

• 28664-08-6 6,6-dimethyl-norpinan-2-ol 
• 19620-36-1 4-(propan-2-ylidene)cyclohexan-1-one 
• 110-86-1 pyridine 
• 289-95-2 PYRIMIDINE 
• 117648-73-4 10,10-Dimethyl-3-aza-tricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene 
• 34771-45-4 5-phenylpyrimidine 
• 92-07-9 3,5-diphenylpyridine 
• 117648-75-6 10,10-Dimethyl-5-phenyl-3-aza-tricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene 
• 26409-32-5 3,5-bis(4-methylphenyl)pyridine 
• 74963-04-5 5-(4-methyl phenyl)pyrimidine 
• 117648-77-8 10,10-Dimethyl-5-p-tolyl-3-aza-tricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene 
• 82525-17-5 5-(4-chlorophenyl)pyrimidine 
• 117648-78-9 5-(4-Chloro-phenyl)-10,10-dimethyl-3-aza-tricyclo[7.1.1.0^2,7]undeca-2⁽⁷⁾,3,5-triene 
• 26409-33-6 3,5-bis-(4-methoxyphenyl)-pyridine 

Relevant academic research and scientific papers

Scale-Up of Ozonolysis using Inherently Safer Technology in Continuous Flow under Pressure: Case Study on β-Pinene

Despite its synthetic relevance, ozonolysis is still an underused reaction in the synthetic chemistry industries. This can be attributed to safety issues while handling the ozone itself, alongside extra hazard related to unstable reaction intermediates. Flow chemistry is inherently safer as it involves a small volume of reagent at any given time. Here, to address safety and technical issues, we describe the design and testing of an ozone dosing line. A global risk assessment and the description of the setup, the analytics, are presented in detail. This new dosing line enabled the successful scale-up of β-pinene ozonolysis in flow, with a productivity of over 16 g/h.

Oxidative Cleavage of Alkenes by O2with a Non-Heme Manganese Catalyst

The oxidative cleavage of C═C double bonds with molecular oxygen to produce carbonyl compounds is an important transformation in chemical and pharmaceutical synthesis. In nature, enzymes containing the first-row transition metals, particularly heme and non-heme iron-dependent enzymes, readily activate O2 and oxidatively cleave C═C bonds with exquisite precision under ambient conditions. The reaction remains challenging for synthetic chemists, however. There are only a small number of known synthetic metal catalysts that allow for the oxidative cleavage of alkenes at an atmospheric pressure of O2, with very few known to catalyze the cleavage of nonactivated alkenes. In this work, we describe a light-driven, Mn-catalyzed protocol for the selective oxidation of alkenes to carbonyls under 1 atm of O2. For the first time, aromatic as well as various nonactivated aliphatic alkenes could be oxidized to afford ketones and aldehydes under clean, mild conditions with a first row, biorelevant metal catalyst. Moreover, the protocol shows a very good functional group tolerance. Mechanistic investigation suggests that Mn-oxo species, including an asymmetric, mixed-valent bis(μ-oxo)-Mn(III,IV) complex, are involved in the oxidation, and the solvent methanol participates in O2 activation that leads to the formation of the oxo species.

Synthesis and surface spectroscopy of α-pinene isotopologues and their corresponding secondary organic material

Atmospheric aerosol-cloud interactions remain among the least understood processes within the climate system, leaving large uncertainties in the prediction of future climates. In particular, the nature of the surfaces of aerosol particles formed from biogenic terpenes, such as α-pinene, is poorly understood despite the importance of surface phenomena in their formation, growth, radiative properties, and ultimate fate. Herein we report the coupling of a site-specific deuterium labeling strategy with vibrational sum frequency generation (SFG) spectroscopy to probe the surface C-H oscillators in α-pinene-derived secondary organic aerosol material (SOM) generated in an atmospheric flow tube reactor. Three α-pinene isotopologues with methylene bridge, bridgehead methine, allylic, and vinyl deuteration were synthesized and their vapor phase SFG spectra were compared to that of unlabeled α-pinene. Subsequent analysis of the SFG spectra of their corresponding SOM revealed that deuteration of the bridge methylene C-H oscillators present on the cyclobutane ring in α-pinene leads to a considerable signal intensity decrease (ca. 30-40%), meriting speculation that the cyclobutane moiety remains largely intact within the surface bound species present in the SOM formed upon α-pinene oxidation. These insights provide further clues as to the complexity of aerosol particle surfaces, and establish a framework for future investigations of the heterogeneous interactions between precursor terpenes and particle surfaces that lead to aerosol particle growth under dynamically changing conditions in the atmosphere.

Design, synthesis and biological evaluation of novel β-pinene-based thiazole derivatives as potential anticancer agents via mitochondrial-mediated apoptosis pathway

A series of novel β-pinene-based thiazole derivatives were synthesized and characterized by HRMS, 1H NMR, and 13C NMR analyses as potential antineoplastic agents. Derivatives were evaluated for their anticancer activities in vitro, and the data manifested that most target compounds showed potent anti-proliferative activities against three human cancer cell lines. Especially, compound 5g displayed excellent cytotoxic activity against Hela, CT-26, and SMMC-7721 cell lines with IC50 values of 3.48 ± 0.14, 8.84 ± 0.16, and 6.69 ± 0.15 μM, respectively. To determine the underlying mechanism of compound 5g on cell viability, DAPI staining, Annexin-V/PI staining, JC-1 staining, DCFDA staining, and Western blot analysis were performed. Our data showed that compound 5g inhibited cell proliferation by inducing apoptosis and cell cycle arrest of Hela cells at the G0/G1 phase in a dose dependent manner. Further studies revealed that compound 5g enhanced levels of reactive oxygen species (ROS), caused a decrease in mitochondrial membrane potential, increased the release of mitochondrial cytochrome C, and affected the expression of Bax, Bcl-2, caspase-3 and caspase-9. Thus, our findings indicated that compound 5g induced apoptosis in Hela through ROS-mediated mitochondrial dysfunction signaling pathways.

PINENE-DERIVED DIISOCYANATES

A pinene-derived diisocyanate compound, a process for forming a pinene-derived diisocyanate compound, and an article of manufacture containing a polyurethane polymer are disclosed. The process for forming the pinene-derived diisocyanate compound includes oxidizing the pinene to form a pinene-derived ketone compound, converting the pinene-derived ketone compound to a diamine compound in subsequent reaction steps, and reacting the diamine compound with phosgene to form the pinene-derived diisocyanate compound. The polyurethane polymer is synthesized in a reaction between a pinene-derived diisocyanate compound and a polyol.

Computer assisted design and synthesis of novel chiral piperazine derivatives from 3-hydroxynopinone

Background: Hepatitis C virus (HCV) Flaviviridae family comprises of positive sense singlestranded RNA ((+)ssRNA), which infects 3% of the world population that leads to the liver cirrhosis. There is no permanent cure available without side effects till date. Many drug discovery groups around the globe are heading to discover promising anti-HCV drug candidates for this deadly virus. Therefore, it is an urgent need to identify new anti viral agents that target HCV and ultimately give the permanent cure. The genome of HCV contains structural proteins (capsid protein C, membrane protein M, envelope protein E) and non-structural proteins (NS1, NS2A, NS2B, NS3, NS4A, NS4B, and NS5). Protease/helicase NS3 is one non-structural protein, a multifunctional enzyme with serine-protease and NTPase/helicase activities implicated in the processing of viral polyprotein and to make copies of the HCV genome. Methods: A simple and efficient method has been developed for the synthesis of designed chiral piperazine ligands through the condensation of 1,2-diamino-cyclohexane or 1,2-diphenylethylenediamine with 3-hydroxynopinone derived from β-pinene in 4 steps with overall very good yields. Results: Four new piperazine based molecules have been designed, synthesized with limited DLP violations, good QPlogP, QPlogS values and excellent human % oral absorption values using Schrodinger suite. All the molecules showed better binding scores (G-Score & DG-Score) for drug like molecules. Conclusion: Molecular docking insights, interaction profiles and synthetic feasibilities of these molecules suggest that these could become good biologically active compounds against HIV and HCV. In future, we synthesized high enantiomeric excess biologically potent molecules with these diamine piperazine chiral auxiliaries.

Design, synthesis and anticancer activity of novel nopinone-based thiosemicarbazone derivatives

A series of new nopinone-based thiosemicarbazone derivatives were designed and synthesized as potent anticancer agents. All these compounds were identified by 1H NMR, 13C NMR, HR-MS spectra analyses. In the in vitro anticancer activity, most derivatives showed considerable cytotoxic activity against three human cancer cell lines (MDA-MB-231, SMMC-7721 and Hela). Among them, compound 4i exhibited most potent antitumor activity against three cancer cell lines with the IC50 values of 2.79?±?0.38, 2.64?±?0.17 and 3.64?±?0.13?μM, respectively. Furthermore, the cell cycle analysis indicated that compound 4i caused cell cycle arrest of MDA-MB-231 cells at G2/M phase. The Annexin V-FITC/7-AAD dual staining assay also revealed that compound 4i induced the early apoptosis of MDA-MB-231 cells.

Continuous flow ozonolysis in a laboratory scale reactor

Several important types of ozonolysis reactions have been performed in a continuous flow device that is able to perform both the ozonolysis and quenching steps in flow mode. This technique allows safe and scalable ozonolysis reactions to be performed on a laboratory scale.(Figure Presented)

Iron-catalyzed epoxidation of aromatic olefins and 1,3-dienes

The combination of iron(III) chloride, pyridine-2,6-dicarboxylic acid and formamidine ligands allows for the epoxidation of styrenes and conjugated dienes in excellent chemoselectivity and yields.

OZONOLYSIS OF AROMATICS AND/OR OLEFINS

The invention pertains to a process for oxidizing unsaturated starting materials, comprising: (i) providing a liquid composition containing an olefin and/or aromatic starting compound, (ii) compressing an ozone-containing gas to a pressure of at least 5 bar absolute, (iii) introducing the compressed ozone-containing gas in one or more microreactors, bringing said gas into contact with said liquid composition (i), to obtain an ozonide, (iv) and optionally subjecting said ozonide to oxidative or reductive degradation. The use of compressed ozone makes it possible to mix large gas volumes with small liquid volumes, and achieve satisfactory contact between the gas and liquid reactants. This dramatically improves yields over conventional micro-reactor-driven ozonolysis.