6089-04-9

Usage

Uses

Used in Chemical Synthesis:
TETRAHYDRO-2-(2-PROPYNYLOXY)-2H-PYRAN is used as a key intermediate in the preparation of 1,3-dienyl acetal. Its unique reactivity with electrophiles makes it a valuable compound for creating complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, TETRAHYDRO-2-(2-PROPYNYLOXY)-2H-PYRAN may be utilized as a building block for the development of new drugs or drug candidates. Its ability to react with various electrophiles can be exploited to synthesize novel compounds with potential therapeutic applications.
Used in Material Science:
TETRAHYDRO-2-(2-PROPYNYLOXY)-2H-PYRAN could also be employed in the development of new materials, such as polymers or coatings, due to its chemical properties and reactivity. Its versatility in forming different types of chemical bonds can contribute to the creation of innovative materials with unique properties.

Synthesis Reference(s)

Chemistry Letters, 6, p. 817, 1977Organic Syntheses, Coll. Vol. 7, p. 334, 1990Synthetic Communications, 19, p. 901, 1989 DOI: 10.1080/00397918908051010

InChI:InChI=1/C8H12O2/c1-2-6-9-8-5-3-4-7-10-8/h1,8H,3-7H2/t8-/m0/s1

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 107-19-7 propargyl alcohol 
• 3174-74-1 dihydropyran 
• 64244-47-9 4-(tetrahydro-pyran-2-yloxy)-but-2-yn-1-ol 
• 36551-06-1 3-(tetrahydropyran-2-yloxy)-1-trimethylsilylprop-1-yne 
• 199998-50-0 2-bromomethoxy-tetrahydro-pyran 
• 927-74-2 3-Butyn-1-ol 
• 694-54-2 tetrahydro-2H-2-pyranol 
• 106-96-7 propargyl bromide 
• 142-68-7 TETRAHYDROPYRANE 
• 51926-85-3 <3-Chlor-propin-(2)-yl>-pyranyl-aether 
• 104-15-4 toluene-4-sulfonic acid 

Downstream Products

• 6261-22-9 pent-2-yn-1-ol 
• 55542-26-2 17,23-dihydroxy-21,24-dinor-17βH-chol-4-en-20-yn-3-one 
• 764-60-3 hex-2-yn-1-ol 
• 7218-52-2 4-hydroxy-2-butynoic acid 
• 1002-36-4 hep-2-yn-1-ol 
• 32114-34-4 hex-2-yne-1,6-diol 
• 52804-67-8 5-Hydroxy-1-phenyl-pent-3-yn-2-one 
• 4117-14-0 2-decyn-1-ol 
• 6455-33-0 3-nitro-5-tetrahydropyran-2-yloxymethyl-isoxazole 
• 20739-58-6 2-octyn-1-ol 
• 51887-25-3 tridec-2-yn-1-ol 
• 4117-08-2 dec-9-en-2-yn-1-ol 
• 5871-10-3 2,5,8,11-tetradecatetrayne-1-ol 
• 61794-47-6 1-(4-trifluoromethyl-2,3,5,6-tetrafluorophenyl)-1-propyn-3-ol 

Relevant academic research and scientific papers

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Unsaturated acyclic analogues of 2'-deoxyadenosine and thymidine containing fluorine: Synthesis and biological activity

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A novel oxidative cleavage reaction of propargyl alcohol derivatives using K2FeO4-Al2O3

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Chiral acyl radical equivalents: 5-exo cyclization of conformationally constrained 1,3-dioxolanyl radicals

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Synthesis and Photoswitching Properties of Bioinspired Dissymmetric I-Pyrone, an Analogue of Cyclocurcumin

Cyclocurcumin (CC), a turmeric curcuminoid with potential therapeutic properties, is also a natural photoswitch that may undergo E/Z photoisomerization under UV light. To be further exploited in relevant biological applications, photoactivation under near-infrared (NIR) irradiation is required. Such requirement can be met through opportune chemical modifications, by favoring two-photon absorption (TPA) probability. Herein, a general and efficient synthesis of a biomimetic 2,6-disubstituted-δ-pyrone analogue of CC is described, motivated by the fact that molecular modeling previews an order of magnitude increase of its NIR TPA compared to CC. Three retrosynthetic pathways have been identified (i) via an aryl-oxazole intermediate or via aryl-diynone through (ii) a bottom-up or (iii) a top-down approach. While avoiding the passage through unstable synthons or low-yield intermediate reactions, only the latest approach could conveniently afford the 2,6-disubstituted-I-pyrone analogue of CC, in ten steps and with an overall yield of 18%. The photophysical properties of our biomimetic analogue have also been characterized showing an improved photoisomerization yield over the parent natural compound. The potentially improved nonlinear optical properties, as well as enhanced stability, may be correlated to the enforcement of the planarity of the pyrone moiety leading to a quadrupolar D-π-A-π-D system.

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