22556-08-7

Usage

Uses

Used in Pharmaceutical Research:
[1S-(1alpha,3beta,4alpha,6alpha)]-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol is used as a key compound in pharmaceutical research for its potential applications in medicine, drug development, and the production of functional materials. Its unique structure and biological properties make it an attractive candidate for the development of new therapeutic agents.
Used in Synthesis of Natural Products and Pharmaceuticals:
[1S-(1alpha,3beta,4alpha,6alpha)]-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol serves as a starting material for the synthesis of various natural products and pharmaceuticals. Its versatility in chemical reactions and potential to be modified or functionalized makes it a valuable building block in the creation of new and improved drugs.
Used in Medicine:
[1S-(1alpha,3beta,4alpha,6alpha)]-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol is used as a biologically active molecule in the field of medicine. Its potential applications in medicine are currently under investigation, and its unique properties may lead to the development of novel treatments for various diseases and conditions.
Used in Drug Development:
In the process of drug development, [1S-(1alpha,3beta,4alpha,6alpha)]-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol is used as a starting point for the design and synthesis of new pharmaceuticals. Its stereochemical complexity and biological activity make it a promising candidate for the development of innovative drugs with improved efficacy and selectivity.
Used in Production of Functional Materials:
The unique structure of [1S-(1alpha,3beta,4alpha,6alpha)]-3,7,7-trimethylbicyclo[4.1.0]heptane-3,4-diol also lends itself to the production of functional materials with specific properties. These materials could have applications in various industries, such as electronics, coatings, and adhesives, where their unique characteristics can be harnessed for improved performance.

Upstream product

• 498-15-7 (+)-Δ³-carene 
• 936-92-5 (1S,3R,4S,6R)-3,4-epoxy-3,7,7-trimethylbicyclo[4.1.0]heptane 
• 936-91-4 3-carene epoxide 
• 10395-46-7 1S,3R,4S,6R-(+)-3β,4β-caranediol 
• 67-64-1 acetone 
• 67-63-0 isopropyl alcohol 
• 79-21-0 peracetic acid 
• 93-59-4 Perbenzoic acid 
• 2311-91-3 monoperoxyphthalic acid 
• 64-17-5 ethanol 
• 13466-78-9 3-carene 
• 936-91-4 (1S,3R,4S,6R)-3,4-epoxycarane 
• 936-91-4 α-3,4-Epoxycarane 

Downstream Products

• 58930-63-5 (3¹R,3³S)-3²,3²-dimethyl-3(1,3)cyclopropyla-5-oxohexanoic acid 
• 24348-06-9 (+)-3β-hydroxy-4-caranone 
• 10309-65-6 (-)-4α-acetoxy-3β-hydroxy-trans-carane 
• 33116-78-8 (1S,3R)-(+)-3-hydroxy-4-isocaranyl tosylate 
• 13124-69-1 4,7,7-trimethylbicyclo[4.1.0]heptan-3-one 
• 809286-04-2 (R)-α-cyano-α-fluoro-p-tolylacetic acid (1R,3R,4R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl ester 
• 809286-03-1 (S)-α-cyano-α-fluoro-p-tolylacetic acid (1R,3R,4R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl ester 
• 863224-93-5 (1R,2R,3R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl (2R)-2-fluoro-2-[4-(2-methylpropyl)phenyl]propionate 
• 863224-94-6 (1R,2R,3R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl (2S)-2-fluoro-2-[4-(2-methylpropyl)phenyl]propionate 
• 886359-84-8 (1R,2R,3R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl (2R)-2-fluoro-2-(4-phenoxyphenyl)propionate 
• 863224-97-9 (1R,2R,3R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl (2R)-2-fluoro-2-(3-fluoro-4-phenylphenyl)propionate 
• 863224-98-0 (1R,2R,3R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl (2S)-2-fluoro-2-(3-fluoro-4-phenylphenyl)propionate 
• 863225-01-8 (1R,2R,3R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl (2R)-2-fluoro-2-[3-(phenylcarbonyl)phenyl]propionate 
• 863225-02-9 (1R,2R,3R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl (2S)-2-fluoro-2-[3-(phenylcarbonyl)phenyl]propionate 

Relevant academic research and scientific papers

Sustainable catalytic protocols for the solvent free epoxidation and: Anti -dihydroxylation of the alkene bonds of biorenewable terpene feedstocks using H2O2 as oxidant

A tungsten-based polyoxometalate catalyst employing aqueous H2O2 as a benign oxidant has been used for the solvent free catalytic epoxidation of the trisubstituted alkene bonds of a wide range of biorenewable terpene substrates. This epoxidation protocol has been scaled up to produce limonene oxide, 3-carene oxide and α-pinene oxide on a multigram scale, with the catalyst being recycled three times to produce 3-carene oxide. Epoxidation of the less reactive disubstituted alkene bonds of terpene substrates could be achieved by carrying out catalytic epoxidation reactions at 50 °C. Methods have been developed that enable direct epoxidation of untreated crude sulfate turpentine to afford 3-carene oxide, α-pinene oxide and β-pinene oxide. Treatment of crude epoxide products (no work-up) with a heterogeneous acid catalyst (Amberlyst-15) results in clean epoxide hydrolysis to afford their corresponding terpene-anti-diols in good yields.

Syntheses and reactions of terpene β-hydroxyselenides and β-hydroxydiselenides

A convenient method for the synthesis of optically active trans-hydroxyselenides and trans-hydroxydiselenides from the bicyclic terpene group based on the reactions of sodium selenide or sodium diselenide with cis- and trans-(+)-3-carane, trans-(+)-2-carane and (-)-β-pinane epoxides is described. The corresponding cis-hydroxy and cis-methoxydiselenides were obtained in the reaction of sodium diselenide with β-hydroxy- and β-methoxytosylates. The influence of a hydroxy group at the β-position on the diastereomeric ratio of the products of the asymmetric methoxyselenenylation of styrene has been established by composition of the products, crystal structure analyses, and theoretical calculations using a DFT method on the B3LYP level (6-311G(d)).

Syntheses of the optically active terpene hydroxyphenylselenides

The optically active hydroxyphenylselenides derived from the p-menthane, carane, and pinane systems have been obtained. Two methods of hydroxyphenylselenides synthesis have been compared. The first method is based on the reaction of alkenes with N-(phenylseleno)succinimide in the presence of water, and the second from epoxides as a result of the reaction with sodium benzeneselenolate. The influence of the substrate structures on the composition of the obtained products has been demonstrated.

A very reliable method for determination of absolute configuration of chiral secondary alcohols by 1H NMR spectroscopy

(Chemical equation presented) Surprisingly stable synperiplanar conformers of CFTA esters have led us to develop a new and very reliable method for assigning absolute configurations of even secondary alcohols having minimal structural differences, such as chiral benzhydrols and α-monodeuterated benzyl alcohols.

INTRODUCTION OF OXYGENATED FUNCTIONAL GROUPS INTO 3-CARENE AND 2-PINENE BY CULTURED CELLS

The biotransformation of the monoterpene hydrocarbons 3-carene and 2-pinene by cell suspension cultures of Nicotiana tabacum and Catharanthus roseus was investigated.The cultures have the ability to regio- and enantioselectively introduce the oxygenated functional groups into the C=C double bond and the allylic positions of the substrates. - Key words: Nicotiana tabacum; Solanaceae; Catharanthus roseus; Apocyanaceae; cultured cells; biotransformation; epoxidation; hydroxylation; carene; pinene.

Oxygen-containing Bicyclic Monoterpenes. 1H, 13C and 17O NMR Spectroscopic and X-Ray Diffraction Studies of Seven Oxidation Products of (+)-3-Carene

Seven oxidation products of (1S,6R)-(+)-3,7,7-trimethylbicyclohept-3-ene 1; (1S,6R)-3,7,7-trimethylbicyclohept-3-en-2-one (3-caren-2-one) 2, (1S,6R)-3,7,7-trimethylbicyclohept-3-en-5-one (3-caren-5-one) 3, (1S,6R)-3,7,7-trimethylbicyclohept-3-ene-2,5-dione (3-carene-2,5-dione) 4, (1S,3S,4R,6R)-(+)-3,7,7-trimethylbicycloheptene 3,4-trans-oxide (trans-3,4-epoxy-3-carene) 5, (1S,3R,4R,6R)-3,7,7-trimethylbicycloheptane-3-exo-4-endo-diol (carane-3-exo-4-endo-diol) 6 and (1S,2R,4R,5R)-1-methyl-4-exo-(1-hydroxy-1-methylethyl)bicyclohexan-2-endo-ol 7 and (1S,6R)-3-endo-7,7-trimethylbicycloheptan-4-one (trans-4-caranone) 8 have been obtained by oxidation with tert-butylchromate, selenium dioxide, hydrogen peroxide and peracetic acid.The 1H, 13C and 17O NMR spectra of the purified oxidation products have been recorded and assigned.In addition to C,H-COSY spectra, the 1J(C,H) coupling constants were especially useful in 13C NMR spectral assignment.The differentiation between isomeric ketones 2 and 3 is based on a clear difference in the 13C NMR shifts of the double bond methyl.The stereochemical structure elucidation of oxide 5 is based on lanthanide shift reagent induced effects.For ketone 8, molecular mechanics (MM) calculations and comparison of experimental and theoretical 3J(H,H) coupling constants are needed for a final structure elucidation.The assignment of 17O NMR lines of diols 6 and 7 is based on literature values.The crystal structures and absolute configurations of pure enantiomers of diols 6 and 7 have been determined by X-ray diffraction.Crystal data: a = 7.659(2), b = 10.804(3), c = 25.509(4) Angstroem, orthorhombic, space group C2221, Z = 8 (6) and a = 8.076(4), b = 8.836(2), c = 12.487(3) Angstroem, orthorhombic, space group P212121, Z = 4 (7).

Monoterpenediol insect repellents

An insect repellent comprising as an active ingredient a monoterpenediol compound having the formula, STR1 wherein R1, R2 and R3 have either one of the following definitions: (i) all of R1, R2 and R3 are hydrogen, (ii) R1 is hydrogen and R2 and R3, taken together, form a carbon-carbon single bond, or (iii) R2 is hydrogen, R1 and R3, taken together, form a carbon-carbon single bond, and the hydroxyl bonded to the carbon atom marked with an asterisk takes an α-configuration.

ONE-POT TWO-STEP SYNTHESIS OF 1,2-DIOL

Diols can be prepared by hydroxilation of alkenes with m-chloroperoxybenzoic acid in water.The process occurs with high yield and complete anti stereospecificity.

Transformations of 3-carene oxide at rhenium-containing catalysts

The transformations of 3-carene oxide at rhenium-containing catalysts were studied.The introduction of rhenium into the catalytic system significantly increases the reaction rate and leads to the formation of compounds not previously encountered in the products from the isomerization of 3-carene oxide, i.e., 3-carene, 3(10),4-caradiene, 3,3,6-trimethylcycloheptanone, and 3-caren-10-ol.

SYNTHESIS OF METHYL 1R-CIS-2,2-DIMETHYL-3-(2-OXOPROPYL)CYCLOPROPANECARBOXYLATE, AN INTERMEDIATE FOR SYNTHETIC PYRETHROIDS

Synthesis of keto ester (1) from (+)-3-carene is described.Ring cleavage is effected by the Beckmann Fragmentation.