4352-44-7

Usage

Physical state

Colorless liquid

Odor

Floral, sweet, and citrus-like

Uses

Flavor and fragrance ingredient in perfumes, soaps, and cosmetics

Function

Stabilizer and fixative in formulations, enhancing the longevity of the scent

Additional use

Precursor in the synthesis of pharmaceuticals and other organic compounds

Safety precautions

May cause skin and eye irritation, handle with care, store and use in a well-ventilated area

InChI:InChI=1/C9H16O/c1-2-9(10)8-6-4-3-5-7-8/h2,8-10H,1,3-7H2

Upstream product

• 107-02-8 acrolein 
• 931-50-0 cyclohexylmagnesium bromide 
• 931-51-1 cyclohexylmagnesiumchloride 
• 132350-01-7 2-(1-chloro-2-propenyl)-1,3,2-dioxaborinane 
• 1826-67-1 vinyl magnesium bromide 
• 145904-33-2 O-(1-Benzotriazol-1-yl-1-cyclohexylmethyl)benzophenone oxime 
• 2043-61-0 cyclohexanecarbaldehyde 
• 97563-45-6 1-cyclohexylprop-2-yn-1-ol 
• 593-66-8 vinyliodide 
• 464169-79-7 2-cyclohexyl-3-trimethylsilylmethyl-oxirane 
• 3536-96-7 vinylmagnesium chloride 
• 1822-73-7 phenylthioethylene 
• 1119-22-8 divinyl zinc 
• 108-22-5 Isopropenyl acetate 

Downstream Products

• 95124-06-4 (S)-1-cyclohexyl-2-propen-1-ol acetate 
• 2177-34-6 1-cyclohexylprop-2-en-1-one 
• 4798-45-2 4-methyl-pent-1-en-3-ol 
• 1123-86-0 cyclohexyl ethyl ketone 
• 58649-21-1 (E)-(3-chloroprop-1-en-1-yl)cyclohexane 
• 132621-48-8 (1S,2S)-1-cyclohexylglycidol 
• 123001-07-0 (-)-(1R)-1-Hydroxy-1-cyclohexyl-2-propene 
• 4352-44-7 (R)-1-cyclohexyl-prop-2-enol 
• 144222-05-9 1-cyclohexyl-1-(benzyloxy)-2-propene 
• 144222-06-0 3-(3-cyclohexylprop-1-en)-yl benzoate 
• 137156-30-0 Phosphoric acid 1-cyclohexyl-allyl ester diethyl ester 
• 59637-31-9 5-cyclohexylpent-4-en-2-ol 
• 140439-84-5 anti-3-cyclohexylpent-4-en-2-ol 
• 140439-84-5 syn-3-cyclohexylpent-4-en-2-ol 

Relevant academic research and scientific papers

Cobalt-Catalyzed Diastereo- And Enantioselective Reductive Allyl Additions to Aldehydes with Allylic Alcohol Derivatives via Allyl Radical Intermediates

Catalytic generation of ambiphilic π-allyl-metal complexes and their utility in enantioselective transformations constitutes a powerful approach for introduction of allyl groups to a molecule. Herein an unprecedented cobalt-catalyzed highly site-, diastereo-, and enantioselective protocol for stereoselective formation of nucleophilic allyl-Co(II) complexes followed by addition to aldehydes is presented. The reaction features diastereo- and enantioconvergent conversion of easily accessible allylic alcohol derivatives to diversified enantioenriched homoallylic alcohols with a remarkably broad scope of allyl groups that can be introduced. Mechanistic studies indicated that allyl radical intermediates were involved in this process. These new discoveries establish a new strategy for development of enantioselective transformations through capture of radicals by chiral Co complexes, pushing forward the frontier of Co complexes for enantioselective catalysis.

Stereoselective Synthesis of Oxacycles via Ruthenium-Catalyzed Atom-Economic Coupling of Propargyl Alcohols and Michael Acceptors

Synthesis of β-hydroxyenones and its application toward development of tetrahydro-4H-pyran-4-one in an atom-economic fashion is limited. This manuscript describes a ruthenium-catalyzed atom-economic coupling of pent-2-yne-1,5-diols and Michael acceptors as an efficient route for the synthesis of β-hydroxyenones with excellent yields and high regioselectivity. The β-hydroxyenones further undergo a 6-endo trig cyclization under acid-catalyzed conditions to deliver the tetrahydro-4H-pyran-4-ones with high diastereoselectivity. An intramolecular aldol condensation under mild basic conditions and palladium-catalyzed oxidative aromatization was developed for the synthesis of hexahydro-6H-isochromen-6-ones and isochromanols, respectively, from highly substituted tetrahydro-4H-pyran-4-ones with excellent yield and diastereoselectivity. Overall, this work demonstrates the synthetic potential toward the synthesis of oxacycles like tetrahydro-4H-pyran-4-ones, hexahydro-6H-isochromen-6-ones, and isochromanols via an atom-economic catalysis.

Stereoselective Dehydroxyboration of Allylic Alcohols to Access (E)-Allylboronates by a Combination of C-OH Cleavage and Boron Transfer under Iron Catalysis

Iron-catalyzed direct SN2′ dehydroxyboration of allylic alcohols has been developed to access (E)-stereoselective allylboronates. Allylic alcohols with diverse structures and functional groups, especially derived from natural products, underwent smooth transformation. The six-membered ring transition state formed by allylic alcohols and iron-boron intermediate was indicated to be the key component involved in transfer of the boron group, activation of the C-OH bond, and control of the stereoselectivity.

Using Neighboring-Group Participation for Acyclic Stereocontrol in Diastereoselective Substitution Reactions of Acetals

Neighboring-group participation of an ester enabled stereocontrol in substitution reactions of acyclic acetals. The ester group formed a trans-fused dioxolenium ion intermediate, which underwent a substitution reaction at the acetal carbon atom to afford the product with high diastereoselectivity. Neighboring-group participation was confirmed by isolating dioxolane products resulting from nucleophilic addition at C-2 of a 1,3-dioxolenium ion intermediate. Using a pivaloate ester as the participating group in combination with strong nucleophiles produced substitution products with diastereoselectivities of ≥90:10.

Visible-Light Photoredox-Catalyzed α-Regioselective Conjugate Addition of Allyl Groups to Activated Alkenes

The α-regioselective conjugate addition of allyl groups to activated alkenes is a poorly explored area of research. Herein, we report an α-adduct and (E)-isomer selective conjugate addition of allylsilanes to activated alkenes by visible-light photoredox catalysis. The reaction involves allylic radicals that can be generated from allylsilanes through a photoinduced single-electron transfer mechanism. (Figure presented.).

Method for preparing chiral gamma-amino alcohol and chiral alpha-allyl alcohol by one-pot method

The invention relates to a method for preparing chiral gamma-amino alcohol and chiral alpha-allyl alcohol by a one-pot method. The method comprises the following steps: making a racemic alpha-allyl alcohol compound, an amine compound, a chiral ruthenium complex and an alkaline reagent react in an organic solvent, and carrying out separation and purification after completion of the reaction, so that chiral gamma-aminoalcohols and chiral alpha-allylalcohol are prepared, wherein a chiral ruthenium complex is selected from one of them. According to the preparation method of the chiral compound, two chiral compounds with wide purposes, namely the chiral gamma-amino alcohol and the chiral alpha-allyl alcohol, are obtained at the same time through a one-pot reaction, the reaction is simple, the atom economy is high, few by-products are produced, and the requirements of green chemistry are met.

A new monooxygenase from: Herbaspirillum huttiense catalyzed highly enantioselective epoxidation of allylbenzenes and allylic alcohols

Asymmetric epoxidation is a green route to enantiopure epoxides, but often suffers from low enantioselectivity toward unconjugated terminal alkenes. Mining of the NCBI non-redundant protein sequences with a reconstructed ancestral sequence based on six st

Photochemical Alkene Isomerization for the Synthesis of Polysubstituted Furans and Pyrroles under Neutral Conditions

A photochemical approach to polysubstituted heterocycles using UV-induced alkene isomerization is described. The method allows for the synthesis of disubstituted furans and pyrroles under mild and neutral conditions and also provides access to a class of trisubstituted furans pertinent to natural-product synthesis. The method has broad functional-group tolerance and many richly decorated heterocycles have been prepared incorporating functional groups that are unstable under Br?nsted and Lewis acidic conditions.

One-Pot Conversion of Allylic Alcohols to α-Methyl Ketones via Iron-Catalyzed Isomerization-Methylation

A one-pot iron-catalyzed conversion of allylic alcohols to α-methyl ketones has been developed. This isomerization-methylation strategy utilized a (cyclopentadienone)iron(0) carbonyl complex as precatalyst and methanol as the C1 source. A diverse range of allylic alcohols undergoes isomerization-methylation to form α-methyl ketones in good isolated yields (up to 84% isolated yield).

A Convenient Palladium-Catalyzed Carbonylative Synthesis of (E)-3-Benzylidenechroman-4-ones

A convenient palladium-catalyzed carbonylation reaction for the efficient synthesis of (E)-3-benzylidenechroman-4-ones has been developed. Using TFBen as a solid CO source, a range of substituted (E)-3-benzylidenechroman-4-ones were prepared in moderate to good yields with 2-iodophenols and allyl chlorides as the substrates. Additionally, substituted quinolin-4(1H)-ones can also be obtained with 2-iodoaniline as the starting material.