17699-09-1

Basic information

• Product Name: Dihydrocarveol
• Synonyms: (+-)-Dihydrocarveol; EINECS 253-755-5; (1alpha,2beta,5alpha)-2-Methyl-5-(1-methylvinyl)cyclohexan-1-ol; Cyclohexanol, 2-methyl-5-(1-methylethenyl)-, (1R,2R,5R)-rel-; Cyclohexanol, 2-methyl-5-(1-methylethenyl)-, (1alpha,2beta,5alpha)-; 2-methyl-2-(prop-1-en-2-yl)cyclohexanol
• CAS NO: 17699-09-1
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.2493
• EINECS: 253-755-5
• Mol File: 17699-09-1.mol
• Article Data: 64

Chemical Properties

• Boiling Point: 191.9°C at 760 mmHg
• Flash Point: 81°C
• Density: 0.921g/cm³
• Vapor Pressure: 0.134mmHg at 25°C
• Refractive Index: 1.476
• CAS DataBase Reference: Dihydrocarveol(CAS DataBase Reference)
• NIST Chemistry Reference: Dihydrocarveol(17699-09-1)
• EPA Substance Registry System: Dihydrocarveol(17699-09-1)

Safety Data

• Hazardous Substances Data: 17699-09-1(Hazardous Substances Data)

Upstream product

• 18383-49-8 carvone epoxide 
• 31198-76-2 carvoxime 
• 109-99-9 tetrahydrofuran 
• 5989-27-5 D-limonene 
• 99-48-9 (4R,6R)-carveol 
• 5524-05-0 (2R,5R)-5-isopropenyl-2-methylcyclohexanone 
• 5989-54-8 (-)-(S)-limonene 
• 117152-62-2 Imidazole-1-carbothioic acid S-[(E)-(R)-2-methyl-6-(2-thioxo-[1,3]dioxolan-4-yl)-hept-2-enyl] ester 
• 6485-40-1 (R)-Carvone 
• 18383-51-2 (-)-trans-carveol 
• 5524-05-0 (-)-dihydrocarvone 
• 555-31-7 aluminum isopropoxide 
• 67-63-0 isopropyl alcohol 
• 2244-16-8 (S)-p-mentha-6,8-dien-2-one 

Downstream Products

• 5055-99-2 (+)-(1S,2S,5S)-carvomenthyl tosylate 
• 1423157-44-1 (1R,2R,5R)-5-(1,1-di(hydroperoxy)ethyl)-2-methylcyclohexanol 
• 7712-37-0 8-hydroxy-p-menthan-2-one 
• 5199-41-7 3.5-dinitro-benzoic acid-((1S:2S:4S)-p-menthen-⁽⁸⁾-yl-⁽²⁾-ester) 
• 140924-69-2 (1R,2S,4R)-p-menthane-2,8-diol 

Relevant articles and documents

Influence of a hydroxy group in the asymmetric reduction of selenides: Enantioselective synthesis of naturally occurring monoterpenes

The reductive cleavage of the benzenseleno-group in trans-β- hydroxyselenides, to yield a stereogenic methyne center, has been investigated. When the reaction is carried out with lithium in diethylamine, the equilibrated carbanionic intermediate traps the proton of the neighbouring hydroxy function, blocking the stereogenic center as a product with a predictable chirality. Using this strategy, several natural monoterpenes in enantiomerically pure form have been prepared.

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Synthesis of optically active dihydrocarveol via a stepwise or one-pot enzymatic reduction of (R)- and (S)-carvone

A recombinant enoate reductase LacER from Lactobacillus casei catalyzed the reduction of (R)-carvone and (S)-carvone to give (2R,5R)-dihydrocarvone and (2R,5S)-dihydrocarvone with 99% and 86% de, respectively, which were further reduced to dihydrocarveols by a carbonyl reductase from Sporobolomyces salmonicolor SSCR or Candida magnolia CMCR. For (R)-carvone, (1S,2R,5R)-dihydrocarveol was produced as the sole product with >99% conversion, while (1S,2R,5S)-dihydrocarveol was obtained as the major product, but with a lower de when (S)-carvone was used as the substrate. The one-pot reduction was performed at a 0.1 M substrate concentration, indicating that it might provide an effective synthetic route to this type of chiral compound.

REDUCTION OF CARBONYL COMPOUNDS VIA HYDROSILYLATION. V. SYNTHESIS OF OPTICALLY ACTIVE ALLYLIC ALCOHOLS VIA REGIOSELECTIVE ASYMMETRIC HYDROSILALATION

Regioselective asymmetric reduction of prochiral α,β-unsaturated ketones to optically active allylic alcohols was performed via hydrosilylation catalyzed by a rhodium(I) complex with (+)-BMPP, (+)-DIOP and (-)-DIOP as chiral ligands.The allylic alcohols with optical purity up to 69percent e.e. were obtained in good yields.The extent of asymmetric induction was found to depend on the stereoelectronic matching of the chiral ligand, ketone and hydrosilane employed.In the asymmetric reduction of (R)-carbone, leading to carveol, the extent of asymmetric induction was found todepend markedly on the ligand/rhodium ratio.Either trans-(5R,1S)-carveol or cis-(5R,1R)-carveol was obtained with good stereoselectivity by using (-)-DIOP or (+)-DIOP as chiral ligand, and it turned out that the chiral center present in carbone had only a slight influence on the asymmetric induction by the chiral catalysts.

Methylene-Linked Bis-NHC Half-Sandwich Ruthenium Complexes: Binding of Small Molecules and Catalysis toward Ketone Transfer Hydrogenation

The complex [Cp*RuCl(COD)] reacts with LH2Cl2 (L = bis(3-methylimidazol-2-ylidene)) and LiBun in tetrahydrofuran at 65 °C furnishing the bis-carbene derivative [Cp*RuCl(L)] (2). This compound reacts with NaBPh4 in MeOH under dinitrogen to yield the labile dinitrogen-bridged complex [{Cp*Ru(L)}2(μ-N2)][BPh4]2 (4). The dinitrogen ligand in 4 is readily replaced by a series of donor molecules leading to the corresponding cationic complexes [Cp*Ru(X)(L)][BPh4] (X = MeCN 3, H2 6, C2H4 8a, CH2CHCOOMe 8b, CHPh 9). Attempts to recrystallize 4 from MeNO2/EtOH solutions led to the isolation of the nitrosyl derivative [Cp*Ru(NO)(L)][BPh4]2 (5), which was structurally characterized. The allenylidene complex [Cp*Ru═C═C═CPh2(L)][BPh4] (10) was also obtained, and it was prepared by reaction of 2 with HCCC(OH)Ph2 and NaBPh4 in MeOH at 60 °C. Complexes 3, 4, and 6 are efficient catalyst precursors for the transfer hydrogenation of a broad range of ketones. The dihydrogen complex 6 has proven particularly effective, reaching TOF values up to 455 h-1 at catalyst loadings of 0.1% mol, with a high functional group tolerance on the reduction of a broad scope of aryl and aliphatic ketones to yield the corresponding alcohols.

Efficient Transfer Hydrogenation of Ketones using Methanol as Liquid Organic Hydrogen Carrier

Herein, we demonstrate an efficient protocol for transfer hydrogenation of ketones using methanol as practical and useful liquid organic hydrogen carrier (LOHC) under Ir(III) catalysis. Various ketones, including electron-rich/electron-poor aromatic ketones, heteroaromatic and aliphatic ketones, have been efficiently reduced into their corresponding alcohols. Chemoselective reduction of ketones was established in the presence of various other reducible functional groups under mild conditions.

Cucurbit[5]uril-mediated electrochemical hydrogenation of α,β-unsaturated ketones

The potential of cucurbit[5]uril to be used as inverse phase transfer catalyst in electrocatalytic hydrogenation of α,β-unsaturated ketones is illustrated. The interaction behavior among isophorone and cucurbit[5]uril was also investigated using cyclic voltammetry and UV/vis absorption spectroscopy. The results concerning to both techniques revealed an enhancement in the intensity of the absorption peak and also in the current cathodic peak of isophorone in presence of cucurbit[5]uril. This achievement is related to the increase of the isophorone solubility in the medium being an indicative of a host-guest complex formation. The electrochemical hydrogenation of isophorone using cucurbit[5]uril was more efficient than others well-stablish methodologies. Regarding to (R)-(+)-pulegone and (S)-(+)-carvone, the use of cucurbit[5]uril leads to an increase of 17% and 9%, on average, respectively, in the yields when compared to the control reaction. The efficiency of selective C=O bond hydrogenation of 1-acetyl-1-cyclohexene was evaluated. The presence of cucurbit[5]uril increased by 12% the hydrogenations yields of 1-acetyl-1-cyclohexene when compared to the control reaction. In this sense, these results open up an opportunity to carry out electrocatalytic reactions within the cucurbit[5]uril environment.