55373-76-7

Usage

Type of compound

Cyclic alcohol with an added ethynyl group

Common use

Building block for the synthesis of other compounds in organic synthesis and chemical research

Physical state

Colorless liquid

Odor

Slightly sweet

Solubility

Insoluble in water, soluble in organic solvents

Structure

Unique structure and reactivity

Application

Useful tool in organic chemistry for creating new molecules and studying reaction mechanisms

InChI:InChI=1/C10H16O/c1-2-10(11)8-6-4-3-5-7-9-10/h1,11H,3-9H2

Upstream product

• 502-49-8 cycloactanone 
• 74-86-2 acetylene 
• 108-94-1 cyclohexanone 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 70277-75-7 lithium acetylide 
• 4301-14-8 acetylenemagnesium bromide 

Downstream Products

• 17339-74-1 1-(cyclooct-1-en-1-yl)ethanone 
• 61967-54-2 1-ethynyl-1-cyclooctene 
• 60727-70-0 ((E)-1-Cyclooct-1-enyl)-ethanone 
• 1446099-89-3 (E)-1-(2-(dimethyl(phenyl)silyl)vinyl)cyclooctanol 
• 733048-01-6 (Z)-1-[2-(dibenzylbromostannyl)vinyl]-1-cyclooctanol 
• 733048-02-7 (Z)-1-[2-(dibenzylchlorostannyl)vinyl]-1-cyclooctanol 

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.

Alkyne Linchpin Strategy for Drug:Pharmacophore Conjugation: Experimental and Computational Realization of a Meta-Selective Inverse Sonogashira Coupling

The late-stage functionalization (LSF) of pharmaceutical and agrochemical compounds by the site-selective activation of C-H bonds provides access to diverse structural analogs and expands synthetically-accessible chemical space. We report a C-H functionalization LSF strategy that hinges on the use of an alkyne linchpin to assemble conjugates of sp2-rich marketed pharmaceuticals and agrochemicals with sp3-rich 3D fragments and natural products. This is accomplished through a template-assisted inverse Sonogashira reaction that displays high levels of selectivity for the meta position. This protocol is also amenable to distal structural modifications of α-amino acids. The transformation of alkyne functionality to other functional groups further highlights the applicative potential. Computational and experimental mechanistic studies shed light on the detailed mechanism. Turnover-limiting 1,2-migratory insertion of the bromoalkyne coupling partner occurs after relatively fast C-H activation. While this insertion occurs unselectively, regioconvergence results from one of the adducts undergoing a 1,2-trialkylsilyl migration to form the alkynylated product. A heterobimetallic Pd-Ag transition structure is essential for product formation in the β-bromide elimination step.

Base-Catalyzed Borylation/B-O Elimination of Propynols and B2pin2 Delivering Tetrasubstituted Alkenylboronates

An efficient approach to tetrasubstituted alkenylboronates via a cascade borylation/B-O elimination of propynols and B2pin2 was disclosed. A series of tetrasubstituted alkenylboronates were readily furnished with this strategy in good yields, with further transformations leading to tetrasubstituted alkenes and β-diketones demonstrating the synthetic potential of the alkenylboronates constructed by this strategy as versatile intermediates in organic synthesis.

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.

Palladium-catalyzed intermolecular [3 + 2] carbocyclization of alkynols and propiolates: An efficient entry to halo-cyclopentadienes

A novel and efficient Pd-catalyzed intermolecular [3 + 2] carbocyclization of alkynols and electron-deficient alkynes for the synthesis of halo-cyclopentadienes (Cps) has been developed. The present protocol employs simple propargyl alcohols as the C3 group to participate in the cyclization reaction, providing a highly convenient and atom-economical entry to the halo-cyclopentadiene framework. The Royal Society of Chemistry.

CYCLOOCT-(EN-)YL DERIVATIVES FOR USE AS FRAGRANCES

This invention relates to substituted cyclooctenes of formula (I), wherein X and R are defined in the specification.

Substituted hepta-1,6-dien-3-ones with green/fruity odours green/galbanum olfactophore model

Following an analysis of available SAR data on green/galbanum-smelling molecules, a series of new 2-substituted hepta-1,6-dien-3-ones and their analogues were prepared and their olfactory properties evaluated. The study allowed to select efficient new odourants - potential substitutes for natural galbanum oil - and to generate an olfactophore model for the green/galbanum note.

Facile approach to versatile chiral intermediates for fused cyclopentanoid natural products

A facile approach to cis- and trans-2-(1-hydroxymethyl)vinyl-1-vinylcyclohexan-1-ols and to the corresponding cyclopentane, cycloheptane, and cyclooctane derivatives has been developed, starting from cycloalkanones involving the key steps of Rupe and Claisen orthoester rearrangements. The formation of intervening products could be explained by allylic strain and π-stacking, respectively.