19889-94-2

Usage

Uses

Used in Pharmaceutical Applications:
[1R-(1alpha,2alpha,3beta,5alpha)]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol is used as a therapeutic agent for its potential anticancer properties. It has shown promise in the treatment of various types of cancer and has been investigated for its potential use in chemotherapy and other cancer treatments.
Used in Antimicrobial Applications:
[1R-(1alpha,2alpha,3beta,5alpha)]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol is used as an antimicrobial agent due to its demonstrated antibacterial, antifungal, and anti-inflammatory effects, making it a compound of interest for potential pharmaceutical and medicinal applications.
Used in Aromatherapy:
[1R-(1alpha,2alpha,3beta,5alpha)]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol is used as a component in essential oils for its pleasant citrus-like odor, contributing to the relaxing and therapeutic effects of aromatherapy.
Used in Flavor and Fragrance Industry:
[1R-(1alpha,2alpha,3beta,5alpha)]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol is used as a flavoring agent and fragrance component in the food and cosmetics industries, leveraging its pleasant citrus-like aroma to enhance the sensory experience of products.

InChI:InChI=1/C10H18O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h6-9,11H,4-5H2,1-3H3/t6-,7-,8+,9-/m0/s1

Upstream product

• 19894-98-5 6,6-dimethyl-2-methylene-bicyclo[3.1.1]heptan-3-ol 
• 1686-14-2 (1R,2R,4S,6R)-2,7,7-trimethyl-3-oxatricyclo[4.1.1.0.^2,4]octane 
• 7785-26-4 (-)-α-pinene 
• 110-82-7 cyclohexane 
• 1058019-16-1 C₁₃H₂₀O 
• 1376603-48-3 (1S,2S,3S,5R)-3-hydroperoxy-2,6,6-trimethylbicyclo[3.1.1]heptane 
• 106356-53-0 B-allyldiisopinocampheylborane 
• 21947-87-5 L-diisopinocampheylborane 
• 18492-59-6 (+)-pinocamphone 
• 473-62-1 (1R,2R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one 
• 1196-00-5 (-)-isopinocampheol 
• 64-17-5 ethanol 
• 24041-60-9 (+)-isopinocampheol 
• 108-88-3 toluene 

Downstream Products

• 14575-93-0 isopinocamphone 
• 14575-99-6 phthalic acid mono-((1S:2S:3S)-pinanyl-⁽³⁾-ester) 
• 5362-50-5 4-methyl-3-penten-1-al 
• 36237-64-6 dihydrocarveol 
• 39166-57-9 (+)-isopinocampheyl acetate 
• 14575-90-7 isopinocamphyl tosylate 

Relevant academic research and scientific papers

Synthesis and Configuration of Neomaclafungin A

The relative and absolute configuration of neomaclafungins were impossible to establish by spectroscopic analyses alone because of the lack of exploitable 1H-1H couplings and nOes between the upper and the lower subunits. This very difficult task now is finally completed by an enantioselective total synthesis of neomaclafungin A (revised) and its diastereomer (reported). The results also provided a key reference for the complete structures for other neomaclafungins and the long-known closely related natural product maclafungin.

Biology-oriented synthesis of a withanolide-inspired compound collection reveals novel modulators of hedgehog signaling

Biology-oriented synthesis employs the structural information encoded in complex natural products to guide the synthesis of compound collections enriched in bioactivity. The trans-hydrindane dehydro-δ-lactone motif defines the characteristic scaffold of the steroid-like withanolides, a plant-derived natural product class with a diverse pattern of bioactivity. A withanolide-inspired compound collection was synthesized by making use of three key intermediates that contain this characteristic framework derivatized with different reactive functional groups. Biological evaluation of the compound collection in cell-based assays that monitored biological signal-transduction processes revealed a novel class of Hedgehog signaling inhibitors that target the protein Smoothened. BIOS delivers a collection of compounds with the trans-hydrindane dehydro-δ-lactone scaffold, which are based on the withanolide natural products, in a stereoselective fashion. A biological investigation of the compounds revealed novel and potent inhibitors of the Hedgehog signaling pathway, which bind to the protein Smoothened.

Synthesis and ultraviolet absorption characteristics of 4-arylidene isopinocamphones from α-pinene

A new series of 4-arylidene isopinocamphones were synthesized from α-pinene which is a natural chemical from pine tree and their ultraviolet absorption characteristics were investigated. (+)Isopinocamphone was obtained from α-pinene by hydroboration-oxidation and then it was reacted with benzaldehyde, p-methylbenzaldehyde, p -methoxybenzaldehyde, p-chlorobenzaldehyde, furfural and p -nitrobenzaldehyde in the presence of alkali catalysts to get 4-arylidene isopinocamphones including 2-benzylidene-4,6,6-trimethylbicyclo[3.1.1]heptan-3-one (1), 2,6,6-trimethyl-4-(4-methyl benzyl)bicyclo[3.1.1]heptane-3-one (2), 2-(4-methoxybenzylidene)-4,6,6-trimethylbicyclo[3.1.1] heptan-3-one ( 3 ), 2-(4-chlorobenzylidene)-4,6,6-trimethylbicyclo[3.1.1]heptan-3-one (4 ), 2-(furan-2-methylene)-4,6,6-trimethylbicyclic [3.1.1] heptane-3-one (5) and 2,6,6-trimethyl-4-(4-nitrobenzylidene)bicyclo[3.1.1]heptan-3-one (6). he structures of 4-arylidene isopinocamphones were determined by FT-IR, 1H NMR, 13/C NMR and GC-MS technique. Their ultraviolet absorption characteristics and light stability was further examined. The results showed that compounds 1 , 2, 3 and 5 could be used as Btype UV absorbents, compounds 4 and 6 could be used as A-type UV absorbents and compounds 6 had both functions as UV-A and UVB types absorbents. The light stability sequence of these compounds was (2 ) > (1) ≈ (3) ≈ (4) ≈(6) > (5).

Use of immobilized transition metal complexes as recyclable catalysts for oxidation reactions with hydrogen peroxide as oxidant

A tetradentate Schiff base (teta), obtained from triethylenetetramine and salicylaldehyde, has been covalently bonded to divinylbenzene cross-linked chloromethylated polystyrene. This chelating ligand, abbreviated as PS-teta (PS = polymeric support), reacts with metal chlorides (Cu2+, Co 2+, and Ni2+) in methanol to give polymerbound transition metal complexes, PS-Cu(II)teta/(Cat-1), PS-Ni(II)teta/(Cat-2), and PS-Co(II)teta/(Cat-3), formation of which has been established by various physiochemical methods and spectroscopic techniques. The catalytic potential of these materials has been tested for the oxidation of various alkenes, alkanes, alcohols, and thioethers in the presence of 30% H2O2 as an oxidant. At the same time, these catalysts are very stable and could be reused in oxidation reactions for more than five times without noticeable loss of their catalytic activity. Springer Science+Business Media B.V. 2011.

Reductive deprotection of propargyl ether by a SmI2-amine-water system and its application to polymer-supported oligosaccharide synthesis

A SmI2-amine-water system instantaneously deprotected aryl and alkyl propargyl ethers in a reductive manner. The utility of the propargyl group as a protecting group in oligosaccharide synthesis, and its application to polymer-supported oligosaccharide synthesis is described.

An improved procedure for the separation of (+) or (-)-isopinocampheol, the major side product of the oxidation workup procedure of Brown's asymmetric crotylborations

Separation of (+) or (-)-isopinocampheol, the major side product of the oxidation workup procedure of Brown's asymmetric reactions such as crotylborations from the desired product is quite tedious and often requires repeated column chromatography. It is discovered that a sublimation process can be used to easily separate this major side product.

Toward the creation of NMR databases in chiral solvents: bidentate chiral NMR solvents for assignment of the absolute configuration of acyclic secondary alcohols.

The absolute configuration of acyclic secondary alcohols can be established from analysis of the chemical shift behaviors of the adjacent carbons in bidentate chiral solvents (R,R)- and (S,S)-1d as formulated in the boxed illustration.

A practical olefin hydroboration under liquid-liquid phase transfer catalysis conditions

The hydroboration of a series of representative olefins under LL-PTC conditions, followed by oxidative workup provides the corresponding alcohols in excellent yields and regio- and stereoselectivity.