3413-44-3

Usage

Uses

Used in Cosmetics and Personal Care Products:
2-Cyclohexen-1-ol, (1R)is used as a fragrance ingredient for its mild, floral scent, enhancing the sensory experience of these products.
Used in Flavor and Perfume Production:
2-Cyclohexen-1-ol, (1R)is used as a key component in the creation of flavors and perfumes, contributing to their unique and pleasant aromas.
Used in Essential Oils:
2-Cyclohexen-1-ol, (1R)is found naturally in essential oils such as ylang ylang oil and rose oil, where it contributes to their characteristic scents and properties.
Safety:
2-Cyclohexen-1-ol, (1R)is considered to be relatively safe for use in these applications, with low acute toxicity and no significant concerns over chronic exposure. However, it is important to follow proper safety precautions when handling and using this chemical to ensure the well-being of both consumers and workers in the industry.

Upstream product

• 930-68-7 cyclohexenone 
• 822-67-3 Cyclohex-2-enol 
• 72029-30-2 (2S,3S)-2,3-epoxy-cyclohexan-1-one 
• 1165952-91-9 cyclohexa-1,3-diene 
• 102834-16-2 (1R,2R)-2-(4-tert-Butyl-benzenesulfinyl)-cyclohexanol 
• 14447-34-8 (+)-(R)-cyclohex-2-en-1-yl acetate 
• 104792-01-0 2-(Toluene-4-sulfinyl)-cyclohexanol 
• 76644-52-5 rac-3-acetoxycyclohexene 
• 116049-67-3 (R₁S₂R_S)-2-p-tolylsulfinylcyclohexanol 
• 286-20-4 cyclohexene oxide 
• 61426-49-1 (1R)-2-bromocyclohex-2-en-1-ol 
• 89450-57-7 3-(diethoxymethylsilyl)cyclohexene 
• 219525-40-3 (R)-carbonic acid cyclohex-2-enyl methyl ester 
• 28170-13-0 thiobenzoic acid potassium salt 

Downstream Products

• 133715-22-7 ethyl (R)-2-cyclohexenylacetate 
• 882175-52-2 tert-butyl-(cyclohex-2-enyloxy)-dimethyl-silane 
• 133775-37-8 (-)-(R)-cyclohex-2-enylacetic acid 
• 133775-36-7 <3aR-(3aα,12α,12aα,12bα)>-12-amino-2,3,3a,4,11,12,12a,12b-octahydro-10-hydroxyisoquino<2,1,8-lma>carbazol-2(1H)-one hydrochloride 
• 133775-35-6 (R)-(2-cyclohexen-1-yl)acetyl chloride 
• 133715-10-3 (3aR,11R,11aR,11bS)-9-Benzyloxy-5-oxo-1,2,3,3a,4,5,10,11,11a,11b-decahydro-5a-aza-benzo[cd]fluoranthene-11-carboxylic acid 
• 1027905-47-0 (3aR,11R,11aR,11bS)-9-Benzyloxy-5-oxo-1,2,3,3a,4,5,10,11,11a,11b-decahydro-5a-aza-benzo[cd]fluoranthene-11-carbonyl azide 
• 133715-24-9 (R) p-Methoxybenzyl (E)-3-[4-benzyloxy-1-(2-cyclohexen-1-yl)acetyl-1H-indol-3-yl]propenoate 
• 133715-11-4 ((3aR,11R,11aR,11bS)-9-Benzyloxy-5-oxo-1,2,3,3a,4,5,10,11,11a,11b-decahydro-5a-aza-benzo[cd]fluoranthen-11-yl)-carbamic acid benzyl ester 
• 5450-83-9 N-(cis-2-hydroxycyclohexyl)benzamide 
• 57707-58-1 cis-2-benzamidocyclohexyl benzoate 
• 5456-63-3 trans-2-hydroxycyclohexylamine hydrochloride 
• 106729-74-2 1,2-cis-2,3-trans-2-benzamido-3-bromocyclohexyl benzoate 
• 116429-76-6 ((3aS,4S,7aS)-4-Bromo-2-ethoxy-2-phenyl-hexahydro-benzooxazol-3-yl)-phenyl-methanone 

Relevant academic research and scientific papers

A novel highly effective chiral lithium amide for catalytic enantioselective deprotonation of meso-epoxides

A highly enantioselective deprotonation of meso-epoxides was achieved by a catalytic amount of a new chiral lithium amide, derived from (2S,3aS,7aS)-2-(pyrrolidin-1-ylmethyl)octahydroindole, in the presence of excess lithium diisopropylamide to afford the corresponding allylic alcohol derivatives up to 94% ee.

Composition of the activated complex in the stereoselective deprotonation of cyclohexene oxide by a chiral lithium amide

Chiral lithium amides are being developed for stereoselective synthesis of chiral allylic alcohols in high yields and with high enantiomeric excess. However, rational design of the amides for improved stereoselectivity by computational methods, for example, has not been possible due to lack of knowledge of the activated complexes involved in the reactions. Kinetic results are presented for the stereoselective deprotonation by lithium (S)-1- (2-pyrrolidinylmethyl)pyrrolidide (1-Li) of cyclohexene oxide 2, in diethyl ether (DEE), to form (S)-2-cyclohexen-1-ol (S)-3 in high enantiomeric excess. The results show that the rate limiting activated complex is composed of one lithium amide monomer and one molecule of 2 and presumably a solvent molecule. The diamine 1 is found to catalyze the deprotonation.

Investigation of site selectivity of the stereoselective deprotonation of cyclohexene oxide using kinetic resolution of isotopic enantiomers in natural abundance

Stereoselective deprotonation of epoxides with lithium amides can occur by abstraction of protons from more than one site. The site selectivity of the deprotonation of cyclohexene oxide by several chiral and achiral lithium amides has been investigated. 2H NMR has been used to measure the relative abundances of the isotopomers of the epoxide containing one deuterium. An isotopic stereoisomer, with deuterium in the site undergoing abstraction, reacts slower than its enantiomer and other isotopomers having protium in the same site due to a kinetic isotope effect. This results in a kinetic resolution yielding a relative excess of the less reactive isotopic stereoisomer. Thus, the relative abundance of such an enantiomer increases when compared with those having protium at the site in question as the reaction proceeds. It can be concluded that deprotonation of cyclohexene oxide using some chiral- and non-chiral lithium amides occurs by βsyn-deprotonation.

New catalysts for the base-promoted isomerization of epoxides to allylic alcohols. Broadened scope and near-perfect asymmetric induction

Optically active (1S,3R,4R)-3-[N-(trans-2,5-dialkyl)pyrrolidinyl] methyl-2-azabicyclo-[2.2.1]heptanes were evaluated as catalysts for the enantioselective β-elimination of meso-epoxides. The (2R,5R)-dimethylpyrrolidinyl-substituted catalyst 4 exhibited ex

Stereoselective synthesis of the a,e-ring bicyclic core of calyciphylline b-Type alkaloids

A stereoselective synthesis of the bicyclic unit constituting the A and E rings of calyciphylline B-Type alkaloids is disclosed. The propionate ester of (1 R)-cyclohex-2-en-1-ol, obtained by enzymatic resolution, is subjected to an Ireland-Claisen rearrangement. Subsequent reduction of the acid, Mitsunobu reaction to introduce a nitrogen functionality, oxidative cleavage to a dialdehyde, and intramolecular aldol and aza-Michael reactions afford the bicyclic subunit.

Catalytic Enantioselective Deprotonation of meso-Epoxides by the Use of Chiral Lithium Amide

Catalytic enantioselective deprotonation of meso-compound is achieved for the first time by the combined use of a catalytic amount of chiral lithium amide, lithium (S)-2-(pyrrolidin-1-ylmethyl)pyrrolidide, and excess lithium diisopropylamide in the presence of 1,8-diazabicycloundec-7-ene.

Synthesis of oxazolidinone from enantiomerically enriched allylic alcohols and determination of their molecular docking and biologic activities

Enantioselective synthesis of functionalized cyclic allylic alcohols via kinetic resolution in transesterifcation with different lipase enzymes has been developed. The influence of the enzymes and temperature activity was studied. By determination of ideal reaction conditions, byproduct formation is minimized; this made it possible to prepare enantiomerically enriched allylic alcohols in high ee's and good yields. Enantiomerically enriched allylic alcohols were used for enantiomerically enriched oxazolidinone synthesis. Using benzoate as a leaving group means that 1 mol % of potassium osmate is necessary and can be obtained high yields 98%. Inhibitory activities of enantiomerically enriched oxazolidinones (8, 10 and 12) were tested against human carbonic anhydrase I and II isoenzymes (hCA I and hCA II), acetylcholinesterase (AChE), and α-glycosidase (α-Gly) enzymes. These enantiomerically enriched oxazolidinones derivatives had Ki values in the range of 11.6 ± 2.1–66.4 ± 22.7 nM for hCA I, 34.1 ± 6.7–45.2 ± 12.9 nM for hCA II, 16.5 ± 2.9 to 35.6 ± 13.9 for AChE, and 22.3 ± 6.0–70.9 ± 9.9 nM for α-glycosidase enzyme. Moreover, they had high binding affinity with ?5.767, ?6.568, ?9.014, and ?8.563 kcal/mol for hCA I, hCA II, AChE and α-glycosidase enzyme, respectively. These results strongly supported the promising nature of the enantiomerically enriched oxazolidinones as selective hCA, AChE, and α-glycosidase inhibitors. Overall, due to these derivatives’ inhibitory potential on the tested enzymes, they are promising drug candidates for the treatment of diseases like glaucoma, leukemia, epilepsy; Alzheimer's disease; type-2 diabetes mellitus that are associated with high enzymatic activity of CA, AChE, and α-glycosidase.

An intriguing effect of polymer-bound lithium amides in catalytic enantioselective rearrangement of meso-epoxides mediated by chiral lithium amides

Polymer-bound lithium dialkylamides were prepared from the corresponding polymer-bound amines and butyllithium. The reagent was successfully employed as an in situ regenerating agent of a chiral lithium amide in a catalytic enantioselective rearrangement of meso-epoxides, and chiral allylic alcohols were obtained in up to 95% ee.

Asymmetric base-promoted epoxide rearrangement: Achiral lithium amides revisited

The use of achiral bases other than lithium diisopropylamide (LDA) was investigated for the asymmetric (1S,3R,4R)-3-(pyrrolidinyl)methyl-2-azabicyclo[2.2.1]heptane catalyzed rearrangement of cyclohexene oxide to (1R)-cyclohex-2-en-1-ol. No significant imp

Catalytic enantioselective deprotonation of meso-epoxides utilising homochiral bis-lithium amide bases

(R)-2-Cyclohexen-1 ol and (R)-2-cyclooctene-1-ol have been prepared in very good ee using R,R-homochiral bis-lithium amide bases derived from homochiral C2 symmetric diamines. (R)-2-Cyclohexen-1-ol has been synthesized in good ee utilising catalytic homochiral bis-lithium amide in the presence of n-butyl lithium.