2809-78-1

Usage

Uses

Used in Pharmaceutical Industry:
1-Ethynyl-1-cycloheptanol is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its alkyne group allows for a wide range of chemical reactions, enabling the creation of diverse drug molecules with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 1-Ethynyl-1-cycloheptanol is utilized as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its unique reactivity contributes to the development of effective and targeted agrochemical products.
Used in Material Science:
1-Ethynyl-1-cycloheptanol is employed in the development of novel materials due to its structural properties. Its alkyne functionality can be exploited in the synthesis of advanced materials with specific properties, such as conductivity, magnetism, or optical characteristics.
Used in Fine Chemicals Industry:
As a key component in the production of fine chemicals, 1-Ethynyl-1-cycloheptanol is used in the synthesis of specialty chemicals with high purity and specific applications in various fields, including fragrances, dyes, and other high-value chemical products.
It is crucial to handle 1-Ethynyl-1-cycloheptanol with care, as it may pose health and environmental hazards if not properly managed. Proper safety measures and disposal methods should be followed to minimize any potential risks associated with 1-ETHYNYL-1-CYCLOHEPTANOL.

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

Upstream product

• 74-86-2 acetylene 
• 502-42-1 cycloheptanone 
• 1066-26-8 sodium acetylide 
• 70277-75-7 lithium acetylide 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 7664-41-7 ammonia 
• 75-85-4 tert-Amyl alcohol 
• 60-29-7 diethyl ether 
• 64-17-5 ethanol 
• 108-94-1 cyclohexanone 
• 4301-14-8 acetylenemagnesium bromide 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 14377-11-8 1-acetyl-1-cycloheptene 
• 100054-87-3 methyl-carbamic acid-(1-ethynyl-cycloheptyl ester) 
• 1027899-14-4 1-[6-chloro-8-(3-fluoro-phenyl)-9-methyl-9H-purin-2-ylethynyl]-cycloheptanol 
• 2809-83-8 1-ethynylcyclohept-1-ene 
• 748155-24-0 7-[2-(1-chloroethylidene)cycloheptyloxy]-4-methyl-2H-chromen-2-one 
• 386731-64-2 2-(2-cycloheptylidene-vinyl)-2-cyclohexa-2,4-dienyl-malonic acid dimethyl ester 
• 3603-86-9 trans-cycloheptane-1,2-dicarboxylic acid 
• 3603-86-9 trans-cycloheptane-1,2-dicarboxylic acid 
• 214493-84-2 Ru(η(5)-indenyl)(bis(diphenylphosphino)methane)((E)-CH=CH-C=CH-(CH2)5) 
• 165679-65-2 (Z)-1-[2-(tri-p-tolylstannyl)vinyl]-1-cycloheptanol 
• 165679-64-1 (Z)-1-[2-(triphenylstannyl)vinyl]-1-cycloheptanol 
• 191791-62-5 (C₉H₇)Ru(((C₆H₅)2PCH₂)2)(CCHC₇H₁₁)⁽¹⁺⁾*PF₆^(1-)=[(C₉H₇)Ru(((C₆H₅)2PCH₂)2)(CCHC₇H₁₁)]PF₆ 
• 618444-60-3 (Z)-1-[2-(tribenzylstannyl)vinyl]-1-cycloheptanol 
• 4158-76-3 hexabenzyl-distannane 

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.

Fluorocyclization of Allyl Alcohols and Amines to Access 3-Functionalized Oxetanes and Azetidines

An efficient method to prepare 3-functionalized oxetanes and azetidines has been realized by fluorocyclization of readily available 2-azidoallyl/2-alkoxyallyl alcohols and amines. Notably, this is the first example applying the fluorocyclization strategy to construct four-membered heterocycles. The pendant electron-donating group (-N3 or -OR) plays a crucial role in polarizing the C= C double bond and facilitating the cyclization process, as verified by DFT and experimental studies.

Enantio- And Diastereodivergent Construction of 1,3-Nonadjacent Stereocenters Bearing Axial and Central Chirality through Synergistic Pd/Cu Catalysis

In contrast to the widely explored methods for the asymmetric synthesis of molecules bearing a single stereocenter or adjacent stereocenters, the concurrent construction of 1,3-stereogenic centers in an enantio- and diastereoselective manner remains a challenge, especially in acyclic systems. Herein, we report an enantio- and diastereodivergent construction of 1,3-nonadjacent stereocenters bearing allenyl axial and central chirality through synergistic Pd/Cu-catalyzed dynamic kinetic asymmetric allenylation with racemic allenylic esters. The protocol is suitable for a wide range of substrates including the challenging allenylic esters with less sterically bulky substituents and provided chiral allenylic products bearing 1,3-nonadjacent stereocenters with high levels of enantio- and diastereoselectivities (up to >20:1 dr and >99% ee). Furthermore, several representative transformations involving axial-to-central chirality transfer were conducted, affording useful structural motifs containing nonadjacent stereocenters in a diastereodivergent manner.

Synthesis of Imidazo[1,2-a]pyridines and Imidazo[2,1-b]thiazoles Attached to a Cycloalkyl or Saturated Heterocycle Containing a Tertiary Hydroxy Substitution

A new method has been developed for the synthesis of imidazo[1,2-a]pyridines, imidazo[2,1-b]thiazoles, and benzo[d]imidazo[2,1-b]thiazoles attached to a cycloalkyl or saturated heterocycle containing a tertiary hydroxy substitution. Readily available substituted 2-aminopyridines, 2-aminothiazoles, and 2-aminobenzothiazoles were treated with bromohydroxycycloalkyl ethanones to afford the desired products in good yields.

Deoxygenative Borylation of Secondary and Tertiary Alcohols

Two different approaches for the deoxygenative radical borylation of secondary and tertiary alcohols are presented. These transformations either proceed through a metal-free silyl-radical-mediated pathway or utilize visible-light photoredox catalysis. Readily available xanthates or methyl oxalates are used as radical precursors. The reactions show broad substrate scope and high functional-group tolerance, and are conducted under mild and practical conditions.

Palladium(II)-Catalyzed Site-Selective C(sp3)?H Alkynylation of Oligopeptides: A Linchpin Approach for Oligopeptide–Drug Conjugation

The palladium(II)-catalyzed C(sp3)?H alkynylation of oligopeptides was developed with tetrabutylammonium acetate as a key additive. Through molecular design, the acetylene motif served as a linchpin to introduce a broad range of carbonyl-containing pharmacophores onto oligopeptides, thus providing a chemical tool for the synthesis and modification of novel oligopeptide–pharmacophore conjugates by C?H functionalization. Dipeptide conjugates with coprostanol and estradiol were synthesized by this method for potential application in targeted drug delivery to tumor cells with overexpressed nuclear hormone receptors.

Facile Alder-Ene Reactions of Silylallenes Involving an Allenic C(sp2)-H Bond

Facile and selective Alder-ene reactions of silylallenes involving the activation of an allenic C(sp2)-H over an allylic C(sp3)-H bond is described. In this ene reaction, the presence of a silyl substituent was found to be critical for the observed reactivity and selectivity since the corresponding alkyl-substituted allenes show different reaction profiles. Computational studies show that the origin of this unusual reactivity is the lower bond dissociation energy of the α-C(sp2)-H bond in silylallenes compared to the corresponding nonsilylated allenes.

Facile synthesis of halogenated spiroketals via a tandem iodocyclization

A strategy for the synthesis of spiroketal compounds through a tandem iodocyclization of 1-(2-ethynylphenyl)-4-hydroxybut-2-yn-1-one derivatives is presented. This reaction could proceed under very mild conditions in a short time and avoid the use of expensive and toxic metal catalysts. Moreover, the resulting halides can be further exploited by subsequent palladium-catalyzed coupling reactions, which act as the important intermediates for building other valuable compounds.

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.

Au-catalyzed formation of functionalized quinolines from 2-alkynyl arylazide derivatives

A new method for converting 2-alkynyl arylazide derivatives into functionalized polysubstituted quinolines following a gold-catalyzed 1,3-acetoxy shift/cyclization/1,2-group shift sequence has been developed. This transformation proceeds under mild reaction conditions, is efficient, and tolerates a large variety of functional groups.