10334-13-1

Basic information

• Product Name: (1R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2α-ol
• Synonyms: (1R,2R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol;(1R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2α-ol;(1R,4R)-Bornan-2α-ol;[1R,2R,4R,(-)]-Bornan-2-ol
• CAS NO: 10334-13-1
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 0
• Mol File: 10334-13-1.mol
• Article Data: 57

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2α-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2α-ol(10334-13-1)
• EPA Substance Registry System: (1R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2α-ol(10334-13-1)

Safety Data

• Hazardous Substances Data: 10334-13-1(Hazardous Substances Data)

Usage

General Description

(1R,4R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2α-ol, also known as α-Terpineol, is a naturally occurring monocyclic monoterpenoid alcohol. It is found in a variety of essential oils, including pine, eucalyptus, and cajeput oils. α-Terpineol is known for its pleasant odor, which is described as lilac-like with a hint of citrus. It is utilized in the fragrance industry as a constituent in perfumes, soaps, and other scented products. The compound also exhibits antimicrobial and anti-inflammatory properties and has been studied for its potential use in pharmaceuticals and as a natural insecticide. Additionally, α-Terpineol has been used in traditional medicine for its calming and sedative effects.

Upstream product

• 76-22-2 Camphor 
• 464-48-2 (1S)-camphor 
• 24393-70-2 isoborneol 
• 736109-58-3 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 125-12-2 isobornyl acetate 
• 13109-70-1 isobornyl butyrate 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 60-29-7 diethyl ether 
• 464-43-7 d-borneol 
• 141-52-6 sodium ethanolate 
• 38970-50-2 l-chimgin 
• 38970-49-9 l-chimganin 
• 64108-13-0 10-chloro-bornan-2-ol 
• 565-00-4 dl-camphene 

Downstream Products

• 89299-71-8 (1S,2S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl 2-chloroacetate 
• 76-22-2 Camphor 
• 5655-61-8 (+)-isobornyl acetate 
• 464-49-3 (1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one 
• 464-48-2 (1S)-camphor 
• 114916-69-7 2-methoxy-4-methylthiobenzoic acid bornyl ester 
• 135607-88-4 diphenylbornyl phosphite 
• 4443-51-0 ((1R)-isobornyl)-methyl ether 
• 94200-10-9 2-Methyl-buttersaeure-isobornylester 
• 565-00-4 dl-camphene 
• 53391-95-0 (+/-)-diisobornyl ether 
• 79-92-5 (+)-camphene 
• 7510-51-2 D-Isoborneol-(4-nitro-benzoat) 
• 736109-58-3 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 

Relevant articles and documents

Molecular cloning and functional characterization of a two highly stereoselective borneol dehydrogenases from Salvia officinalis L

Enzymes for selective terpene functionalization are of particular importance for industrial applications. Pure enantiomers of borneol and isoborneol are fragrant constituents of several essential oils and find frequent application in cosmetics and therapy. Racemic borneol can be easily obtained from racemic camphor, which in turn is readily available from industrial side-streams. Enantioselective biocatalysts for the selective conversion of borneol and isoborneol stereoisomers would be therefore highly desirable for their catalytic separation under mild reaction conditions. Although several borneol dehydrogenases from plants and bacteria have been reported, none show sufficient stereoselectivity. Despite Croteau et al. describing sage leaves to specifically oxidize one borneol enantiomer in the late 70s, no specific enzymes have been characterized. We expected that one or several alcohol dehydrogenases encoded in the recently elucidated genome of Salvia officinalis L. would, therefore, be stereoselective. This study thus reports the recombinant expression in E. coli and characterization of two enantiospecific enzymes from the Salvia officinalis L. genome, SoBDH1 and SoBDH2, and their comparison to other known ADHs. Both enzymes produce preferentially (+)-camphor from racemic borneol, but (?)-camphor from racemic isoborneol.

Chiral β- and γ-aminoalcohols derived from (+)-camphor and (-)-fenchone as catalysts for the enantioselective addition of diethylzinc to benzaldehyde

The addition of Me3SiCN and LiCH2CN to (+)-camphor and (-)-fenchone, respectively, followed by reduction leads to chiral β- and γ-aminoalcohols. The enantioselectivities realized using these aminoalcohols as ligands in the addition of Et2Zn to benzaldehyde were lower than those obtained using the corresponding δ-aminoalcohols.

Treating the camphors with potassium in liquid ammonia leads to a double Horeau duplication

When potassium dissolves in solutions of the enantiomeric camphors R-1 and S-1, variously enantioenriched camphors (1), and racemic camphor RS-1 in liquid ammonia/THF at -77°C, potassium alcoholates of the borneols R-2 and S-2 and isoborrieols R-3 and S-3 plus equivalent amounts of the potassium enolates of R-1 and S-1 - enantiomeric, enantioenriched, and racemic - are produced by a transfer of a β-hydrogen from some 1-derived unit to another [a ketyl disproportionate (hydrogen atom transfer)?]; the exact mechanism is still unknown. Hydrolysis gives enantiomeric, racemic, and enantioenriched 1-3. The mole fractions and enantiomeric compositions (ec's) of 2 and 3 were determined and plotted against the ec's of the substrates 1. The extremes of the resulting three curves are defined by the enantiomers R-1 and S-1 leading to about 1/1 mixtures of R-2 and R-3 and S-2 and S-3, respectively, and the turning points by RS-1 leading to a 9/1 mixture of RS-2 and RS-3. The ec vs ec curve is close to linear in the case of 2 and strongly nonlinear in the case of 3: from enantioenriched substrates 1, one obtains isoborneols 3 with ec's that are strongly amplified with respect to the ec's of the substrates. Fitting the plots into a statistical kinetic model suggests (1) that 3 is formed via one homochiral process (involving units with the same chirality) and 2 via a combination of second homochiral process with a single heterochiral one (involving units with opposite chirality), (2) that the rate-determining steps in these processes are fourth order with respect to the substrates 1 (!), and (3) that all parallel steps have similar or identical rate constants. The homochiral process that leads to 3 amounts to a double Horeau duplication. Statistical oligomerization or condensation of enantioenriched monomers to short oligomers leads to homochiral oligomers with strongly amplified ec. (+)-Camphor R-1 (ec 99.6%) and (-)-camphor S-1 (ec 98.3%) from the chiral pool were not quite enantiopure.

Ketone Reduction by Titanocene Borohydride

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Copper(II) exchanged cation exchange resin: Useful activator in the reduction of ketones

A copper(II) exchanged cation exchange resin has been used as support for reduction of ketones with sodium borohydride. Supported Cu(II) ions activate the reduction of ketones to a large extent and control the stereochemistry of reductions of cyclic ketones resulting in preponderance of equatorial alcohol in most cases.

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A NEW CLASS OF STEREOSELECTIVE REDUCING AGENTS, POTASSIUM 9-ALKYL-9-BORATABICYCLONONANES

A new class of reducing agents, potassium 9-alkyl-9-boratabicyclononanes (K 9-R-9-BBNHs) was examined its stereoselectivity toward cyclic ketones.Among these, K 9-TB-9-BBNH reveals the most favorable stereoselectivity, comparable to that by lithium trisiamylborohydride at 0 deg C.

Reduction of ketones with polydibenzo-18-crown-6-borohydride

Polydibenzo-18-crown-6-(P-DB-18-C-6), a condensation polymer of dibenzo-18-crown-6 and formaldehyde has ben used as support for borohydride ions in the reduction of few cyclic and acyclic ketones. The reagent has been found to be more stereoselective than dibenzo-18-crown-6-borohydride in the reduction of cyclic ketones. 4-t-butylcyclohexanone has been converted exclusively (100%) to trans-4-t-butylcyclohexanol.

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ENANTIOSPECIFIC HYDROLYSIS OF ACETATES OF RACEMIC MONOTERPENIC ALCOHOLS BY SPIRODELA OLIGORRHIZA

Acetates of racemic menthol, borneol, trans-2-hydroxy-trans-dihydropinol, cis-2-hydroxy-trans-dihydropinol and trans-2-hydroxy-cis-dihydropinol undergo enantiospecific hydrolysis in cultures of Spirodela oligorrhiza.R Alcohols are formed faster than S.Absence of light inhibits hydrolysis of the first two acetates.Key Word Index - Spirodela oligorrhiza; Lemnaceae; duckweed; biotransformation; (+/-)-menthyl acetate; (+/-)-bornyl acetate; (+/-)-trans-2-acetoxy-trans-dihydropinol; (+/-)-cis-2-acetoxy-trans-dihydropinol; (+/-)-trans-2-acetoxy-cis-dihydropinol.

Enantioselective Construction of Modular and Asymmetric Baskets

The precise positioning of functional groups about the inner space of abiotic hosts is a challenging task and of interest for developing more effective receptors and catalysts akin to those found in nature. To address it, we herein report a synthetic methodology for preparing basket-like cavitands comprised of three different aromatics as side arms with orthogonal esters at the rim for further functionalization. First, enantioenriched A (borochloronorbornene), B (iodobromonorbornene), and C (boronorbornene) building blocks were obtained by stereoselective syntheses. Second, consecutive A-to-B and then AB-to-C Suzuki–Miyaura (SM) couplings were optimized to give enantioenriched ABC cavitand as the principal product. The robust synthetic protocol allowed us to prepare (a) an enantioenriched basket with three benzene sides and each holding either tBu, Et, or Me esters, (b) both enantiomers of a so-called “spiral staircase” basket with benzene, naphthalene, and anthracene groups surrounding the inner space, and (c) a photo-responsive basket bearing one anthracene and two benzene arms.