57385-16-7

Usage

Uses

Used in Organic Synthesis:
2H-Pyran-4-ol, 4-ethynyltetrahydro(9CI) is used as a building block in organic synthesis for the creation of various complex organic molecules. Its unique structure and reactivity make it a valuable component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Research:
2H-Pyran-4-ol, 4-ethynyltetrahydro(9CI) is used as a key intermediate in pharmaceutical research for the development of new drugs. Its unique properties and reactivity allow for the creation of novel drug candidates with potential therapeutic applications in various diseases and conditions.
Used in Material Science:
2H-Pyran-4-ol, 4-ethynyltetrahydro(9CI) is used in material science for the development of new materials with unique properties. Its incorporation into polymers and other materials can lead to the creation of advanced materials with improved performance characteristics for various applications.

Upstream product

• 29943-42-8 Tetrahydro-4H-pyran-4-one 
• 65032-27-1 ethynylmagnesium chloride 
• 1066-54-2 trimethylsilylacetylene 
• 108-94-1 cyclohexanone 
• 4301-14-8 acetylenemagnesium bromide 
• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 
• 1044277-44-2 4-((trimethylsilyl)ethynyl)tetrahydro-2H-pyran-4-ol 

Downstream Products

• 710321-81-6 3-cyclopentyl-N-[5-(4-hydroxy-tetrahydro-pyran-4-ylethynyl)-pyrazin-2-yl]-2(R)-(4-methanesulfonyl-3-methyl-phenyl)-propionamide 
• 710321-68-9 3-cyclopentyl-N-5-[(4-hydroxy-tetrahydropyran-4-yl-ethynyl)pyrazin-2-yl]-2(R)-(4-methanesulfonyl-phenyl)-propionamide 
• 710321-73-6 2(R)-(3-chloro-4-methanesulfonyl-phenyl)-3-cyclopentyl-N-[5-(4-hydroxy-tetrahydropyran-4-yl-ethyl)-pyrazin-2-yl]-propionamide 
• 1449379-36-5 4-((2-azidophenyl)ethynyl)tetrahydro-2H-pyran-4-yl acetate 
• 1449379-35-4 C₁₃H₁₃N₃O₂ 
• 1449379-34-3 C₁₃H₁₅NO₂ 
• 185206-97-7 1-(4-hydroxytetrahydro-2H-pyran-4-yl)ethanone 

Relevant academic research and scientific papers

NOVEL HETEROAROMATIC AMIDE DERIVATIVE AND MEDICINE CONTAINING SAME

A compound selectively inhibiting Nav1.7 over Nav1.5 is provided. A heteroaromatic amide derivative or salt thereof showing high efficacy for various diseases associated with Nav1.7 such as pain, represented by the general formula (I) [wherein, X1-X2 is N-C or C-N, Y1 , Y2, Y3 and Y4 are -CH2-, -CR4aH- or -O- and so on, Z1 is-O- and so on, ring A is a 3- to 7-membered monocyclic aromatic ring and so on, R1a and R1b are a hydrogen atom or a halogen atom and so on, R2 is a hydrogen atom and so on, R3a, R3b and R3c are a hydrogen atom or an optionally substituted C1-C6 haloalkyl group and so on, R4a, R4b and R4c are, an optionally substituted C1-C6 haloalkyl group or C1-C6 haloalkoxy group and so on, R5a is a hydrogen atom and so on, R5a and R5b together form -CH2O- and so on, R6a and R6b are a hydrogen atom and so on, n is 1 or 2.].

NOVEL PHARMACEUTICAL COMPRISING HETEROAROMATIC AMIDE DERIVATIVE OR SALT THEREOF

PROBLEM TO BE SOLVED: To provide a compound useful for treating or preventing disease associated with voltage-dependent sodium channel (Nav1.7) such as disease involving a pain, disease involving an itch, autonomic nerve-associated disease, or a pharmaceutical composition thereof. SOLUTION: The present disclosure provides a compound illustrated by the following formula, and a pharmaceutical composition containing the same. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

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.

Ligand-Controlled Palladium-Catalyzed Carbonylation of Alkynols: Highly Selective Synthesis of α-Methylene-β-Lactones

The first general and regioselective Pd-catalyzed cyclocarbonylation to give α-methylene-β-lactones is reported. Key to the success for this process is the use of a specific sterically demanding phosphine ligand based on N-arylated imidazole (L11) in the presence of Pd(MeCN)2Cl2 as pre-catalyst. A variety of easily available alkynols provide under additive-free conditions the corresponding α-methylene-β-lactones in moderate to good yields with excellent regio- and diastereoselectivity. The applicability of this novel methodology is showcased by the direct carbonylation of biologically active molecules including natural products.

Synthesis of Bridged Azacycles and Propellanes via Nitrene/Alkyne Cascades

A nitrene/alkyne cascade reaction terminating in C-H bond insertion to form functionalized bridged azacycles from carbonazidates is presented. Due to an initial Huisgen cyclization, all carbonazidates reacted with the alkyne in an exo mode in contrast to the use of sulfamate esters, which react predominately in an endo mode. Substrates with different ring sizes as well as different aryl and heteroaryl groups were also explored. Variation of the nitrene tether showed that 7-membered rings were the maximum ring size to be formed by nitrene attack on the alkyne. Examples incorporating stereocenters on the carbonazidate's tether induced diasteroselectivity in the formation of the bridged ring and two new stereocenters. Additionally, propellanes containing aminals, hemiaminals, and thioaminals formed from the bridged azacycles in the same reaction via an acid-promoted rearrangement.

SUBSTITUTED IMIDAZOLECARBOXYLATE DERIVATIVES AND THE USE THEREOF

A compound is shown in formula (I). The derivatives of the compound include a stereoisomer, a pharmaceutically acceptable salt, a solvate, a prodrug, a metabolite, a deuterated derivative. The compound is a structurally novel substituted imidazole formate derivative. Substituted imidazole formate derivatives are used in preparing a drug with sedative, hypnotic and/or anesthetic effects, as well as a drug that can control the state of epilepsy. The compound has a good inhibitory effect on the central nervous system, and provides a new option for clinical screening of and/or preparation of a drug with sedative, hypnotic and/or anesthetic effects and controlling the state of epilepsy.

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.

Rhodium-Catalyzed Asymmetric Conjugate Alkynylation/Aldol Cyclization Cascade for the Formation of α-Propargyl-β-hydroxyketones

A rhodium-catalyzed conjugate alkynylation/aldol cyclization cascade was developed. Densely functionalized cyclic α-propargyl-β-hydroxyketones were synthesized with simultaneous formation of a C(sp)-C(sp3) bond, a C(sp3)-C(sp3) bond, as well as three new contiguous stereocenters. The transformation was achieved with excellent enantio- and diastereoselectivities using BINAP as the ligand. The synthetic utility of the newly installed alkynyl moiety was exhibited by subjecting the products to an array of derivatizations.

One-Pot, Three-Step Synthesis of Cyclopropylboronic Acid Pinacol Esters from Synthetically Tractable Propargylic Silyl Ethers

Simple propargylic silyl ethers can be converted to complex cyclopropylboronic acid pinacol esters in an efficient one-pot procedure. Terminal acetylenes undergo a Schwartz's reagent catalyzed hydroboration; subsequent addition of further Schwartz's reage

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.