15564-30-4

Usage

Derivative of cyclohexanol

A modified version of the cyclohexanol molecule, which itself is a saturated cycloalkanol.

Ethynyl group (acetylenic group)

A triple-bonded carbon-hydrogen group (-C≡CH) attached to the cyclohexane ring, providing unique reactivity and versatility for chemical transformations.

Methyl group

A single-bonded carbon-hydrogen group (-CH3) attached to the cyclohexane ring, contributing to the compound's structure and reactivity.

Use in organic synthesis

1-Ethynyl-2-methyl-cyclohexanol serves as a valuable building block in the creation of new organic compounds through various chemical reactions.

Intermediate in production

The compound acts as an intermediate in the synthesis of various other compounds, aiding in the formation of the desired end products.

Pharmaceutical

May be used in the development of new drugs or drug delivery systems.

Agrochemical

Could be utilized in the production of pesticides, herbicides, or other agricultural chemicals.

Polymer synthesis

May contribute to the development of new polymer materials with unique properties.

Unique reactivity and versatility

The presence of both the ethynyl and methyl groups allows for a wide range of chemical transformations, making the compound a valuable asset in the development of new compounds.

InChI:InChI=1/C9H14O/c1-3-9(10)7-5-4-6-8(9)2/h1,8,10H,4-7H2,2H3

Upstream product

• 1066-26-8 sodium acetylide 
• 583-60-8 2-Methylcyclohexanone 
• 74-86-2 acetylene 
• 75-20-7 calcium carbide 
• 4301-14-8 acetylenemagnesium bromide 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 32591-08-5 1-ethynyl-2-methyl-cyclohexene 
• 65691-69-2 1-ethynyl-6-methylcyclohex-1-ene 
• 146998-48-3 1-{3-[Bis-(2-chloro-ethyl)-amino]-prop-1-ynyl}-2-methyl-cyclohexanol 
• 2047-97-4 2-methyl-1-acetyl-1-cyclohexene 
• 99183-51-4 (RS)-hydroxy-((1RS)-1-hydroxy-2t-methyl-cyclohex-r-yl)-acetic acid 
• 99183-51-4 (RS)-hydroxy-((1SR)-1-hydroxy-2t-methyl-cyclohex-r-yl)-acetic acid 
• 67902-66-3 cis-1-methyl-2-vinyl-2-acetoxy-cyclohexane 
• 99980-74-2 (+/-)-1-(1-acetoxy-2t-methyl-cyclohex-r-yl)-2,2-dibromo-ethanone 
• 30502-73-9 2,8-nonanedione 
• 115273-64-8 (SR)-((1RS)-1-hydroxy-2c-methyl-cyclohex-r-yl)-ethane-1,2-diol 
• 99183-51-4 (RS)-hydroxy-((1RS)-1-hydroxy-2c-methyl-cyclohex-r-yl)-acetic acid 
• 99183-51-4 (RS)-hydroxy-((1SR)-1-hydroxy-2c-methyl-cyclohex-r-yl)-acetic acid 
• 99980-74-2 (+/-)-1-(1-acetoxy-2c-methyl-cyclohex-r-yl)-2,2-dibromo-ethanone 
• 66477-05-2 1-(1-Chlorvinyl)-6-methyl-1-cyclohexen 

Relevant academic research and scientific papers

Halogen-Substituted Allenyl Ketones through Ring Opening of Nonstrained Cycloalkanols

An efficient synthesis of halogen-substituted allenyl ketones via Ag-catalyzed oxidative ring opening of allenyl cyclic alcohols under mild reaction conditions has been achieved. The reaction features a wide substrate scope and excellent regioselectivity. The synthetic potential of the products has been demonstrated by their conversion to stereodefined alkenes and heterocyclic compounds.

Synthesis of 1,4-Disubstituted 1,2,3-Triazoles via 1,3-Dipolar Cycloaddition/C–N Coupling of Propargyl Alcohols/amines and Aryl Azides

1,4-Disubstituted 1,2,3-triazoles are prepared through the 1,3-dipolar cycloaddition of propargyl (alcohols/amines) and aryl azides in the presence of a mixture of Cu(OAc)2.H2O and NaAs as the catalyst. This method offers the advantages of mild experimental conditions, operational simplicity, and high-to-excellent reaction yields.

Fluoride-assisted activation of calcium carbide: A simple method for the ethynylation of aldehydes and ketones

The fluoride-assisted ethynylation of ketones and aldehydes is described using commercially available calcium carbide with typically 5 mol % of TBAF·3H2O as the catalyst in DMSO. Activation of calcium carbide by fluoride is thought to generate an acetylide "ate"-complex that readily adds to carbonyl groups. Aliphatic aldehydes and ketones generally provide high yields, whereas aromatic carbonyls afford propargylic alcohols with moderate to good yields. The use of calcium carbide as a safe acetylide ion source along with economic amounts of TBAF·3H2O make this procedure a cheap and operationally simple method for the preparation of propargylic alcohols.

Mild conversion of propargylic alcohols to α,β-unsaturated enones in ionic liquids (ILs); A new 'metal free' life for the Rupe rearrangement

A mild and selective transition metal free protocol for the conversion of propargylic alcohols to cyclic and acyclic α,β-unsaturated enones via the Rupe rearrangement is reported. The method utilizes the Br?nsted acidic ionic liquid [BMIM-SO3H][OTf] as catalyst and [BMIM][PF 6] as solvent and offers the potential for recycling and reuse of the IL solvent. The feasibility to synthesize bicyclic fused cyclopentenone derivatives via a Rupe → Aldol → Nazarov sequence utilizing this protocol has also been demonstrated.

Synthesis of acetylenic alcohols with calcium carbide as the acetylene source

Propargyl alcohols containing a terminal alkyne group are highly important and versatile intermediates. Here, we report the synthesis of these compounds from an inexpensive and renewable resource, calcium carbide (CaC2). No metal catalysts are required in this new protocol and the reactions take place under very mild conditions.

98. A Regioselective Cyclohexannulation Procedure via Dienamine Cycloaddition. Synthesis of Functionalised Decalins

A regioselective cyclohexannulation procedure, whose key step involves the cycloaddition of dienamines 12-24 with methyl acrylate, allows the conversion of cycloalkanones 1-11 to bicyclic dienoates 25-37.The chemistry of 26 is briefly examined and, in the context of organoleptic studies concerning functionalised 5,5,9-trimethyldecalins, the transformation of 37 to ketones 44 and 46 as well as to acetates 53-56 is described.