16695-31-1

Basic information

• Product Name: tetrahydro-2-(7-octynyloxy)-2H-pyran
• Synonyms: tetrahydro-2-(7-octynyloxy)-2H-pyran;2-(Oct-7-yn-1-yloxy)tetrahydropyran;2H-Pyran, tetrahydro-2-(7-octyn-1-yloxy)-;2H-Pyran, tetrahydro-2-(7-octynyloxy)-;Einecs 240-740-3;Tetrahydro-2-(7-octyn-1-yloxy)-2H-pyran;2-oct-7-ynoxyoxane
• CAS NO: 16695-31-1
• Molecular Formula: C₁₃H₂₂O₂
• Molecular Weight: 210.31258
• EINECS: 240-740-3
• Mol File: 16695-31-1.mol
• Article Data: 21

Chemical Properties

• Boiling Point: 300.7°C at 760 mmHg
• Flash Point: 108.5°C
• Appearance: /
• Density: 0.94g/cm³
• Vapor Pressure: 0.00197mmHg at 25°C
• Refractive Index: 1.464
• CAS DataBase Reference: tetrahydro-2-(7-octynyloxy)-2H-pyran(CAS DataBase Reference)
• NIST Chemistry Reference: tetrahydro-2-(7-octynyloxy)-2H-pyran(16695-31-1)
• EPA Substance Registry System: tetrahydro-2-(7-octynyloxy)-2H-pyran(16695-31-1)

Safety Data

• Hazardous Substances Data: 16695-31-1(Hazardous Substances Data)

Usage

Uses

Tetrahydro-2-(7-octyn-1-yloxy)-2H-pyran is commonly used as a reagent to synthesize sex pheromones of various insects (e.g. phyllocnistis citrella and autographa gamma L.). Tetrahydro-2-(7-octyn-1-yloxy)-2H-pyran is also used as a reagent to synthesize long chain ω- and (ω-1)-hydroxy fatty acids.

InChI:InChI=1/C13H22O2/c1-2-3-4-5-6-8-11-14-13-10-7-9-12-15-13/h1,13H,3-12H2

Upstream product

• 2009-84-9 (chloro-6' hexyloxy)-2 tetrahydropyranne 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 53963-10-3 2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran 
• 74-86-2 acetylene 
• 14916-80-4 oct-3-yn-1-ol 
• 1066-54-2 trimethylsilylacetylene 
• 20739-58-6 2-octyn-1-ol 
• 110-53-2 1-Bromopentane 
• 34126-19-7 4-octyne-1-ol 
• 2009-83-8 6-chloro-1-hexanol 
• 110-87-2 3,4-dihydro-2H-pyran 
• 63294-76-8 6-<(tetrahydro-2H-pyran-2-yl)oxy>hexyl toluene-4-sulfonate 
• 28659-22-5 6-(tetrahydro-2H-pyranyloxy)hexan-1-ol 
• 4286-55-9 1-bromo-6-hexanol 

Downstream Products

• 871-91-0 oct-7-yn-1-ol 
• 63768-13-8 (E)-7-nonen-1-ol 
• 112775-36-7 (R)-10-Benzyloxy-undec-7-yn-1-ol 
• 112775-38-9 ((R)-10-Bromo-1-methyl-dec-3-ynyloxymethyl)-benzene 
• 112775-35-6 2-((R)-10-Benzyloxy-undec-7-ynyloxy)-tetrahydro-pyran 
• 112775-37-8 Toluene-4-sulfonic acid (R)-10-benzyloxy-undec-7-ynyl ester 
• 112775-40-3 {(2R,3S)-3-[(4R,5S)-5-((E)-(R)-11-Benzyloxy-dodec-1-en-8-ynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranylmethoxy}-tert-butyl-dimethyl-silane 
• 112775-39-0 ((R)-10-Benzyloxy-undec-7-ynyl)-triphenyl-phosphonium; bromide 
• 89045-16-9 8-tetrahydropyranyloxy-2-trimethylstannyl-1-octene 
• 661-69-8 hexamethyldistannane 
• 127599-39-7 (Z,Z)-7,11-Pentacosadiene 
• 104410-91-5 7(Z),11(Z)-nonacosadiene 
• 117299-03-3 1-phenyl-8-(2-tetrahydropyranyloxy)-1-octyne 

Relevant articles and documents

Stereoselective synthesis of (7E,9Z)-7,9-dodecadien-1-yl acetate, (E)-9,11-dodecadien-1-yl acetate, and of (9Z,11E)-9,11-tetradecadien-1-yl acetate by palladium-catalyzed reactions

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Highly Stereoselective Synthesis of Acetates of Mono and Diunsaturated Alcohols and Analogous Aldehydes, Components of Lepidopteran Sex Pheromones, using Tetrakis-palladium

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Discovery of a Fluorinated Enigmol Analog with Enhanced in Vivo Pharmacokinetic and Anti-Tumor Properties

The orally bioavailable 1-deoxy-sphingosine analog, Enigmol, has demonstrated anticancer activity in numerous in vivo settings. However, as no Enigmol analog with enhanced potency in vitro has been identified, a new strategy to improve efficacy in vivo by increasing tumor uptake was adopted. Herein, synthesis and biological evaluation of two novel fluorinated Enigmol analogs, CF3-Enigmol and CF2-Enigmol, are reported. Each analog was equipotent to Enigmol in vitro, but achieved higher plasma and tissue levels than Enigmol in vivo. Although plasma and tissue exposures were anticipated to trend with fluorine content, CF2-Enigmol absorbed into tissue at strikingly higher concentrations than CF3-Enigmol. Using mouse xenograft models of prostate cancer, we also show that CF3-Enigmol underperformed Enigmol-mediated inhibition of tumor growth and elicited systemic toxicity. By contrast, CF2-Enigmol was not systemically toxic and demonstrated significantly enhanced antitumor activity as compared to Enigmol.

Synthesis of (4R,15R,16R,21S)- and (4R,15S,16S,21S)-rollicosin, squamostolide, and their inhibitory action with bovine heart mitochondrial complex I

A convergent stereoselective synthesis of (4R,15R,16R,21S)- and (4R,15S,16S,21S)-rollicosin and squamostolide was accomplished via a Pd-catalyzed cross-coupling reaction. The inhibitory activity of these compounds was examined with bovine heart mitochondrial NADH-ubiquinone oxidoreductase. These compounds showed a remarkably weak inhibitory activity compared to ordinary acetogenins such as bullatacin. Our results indicate that to maintain potent inhibitory effect, the hydroxylated lactone cannot substitute for the hydroxylated mono- or bis-THF rings with a long alkyl chain that can be seen in ordinary acetogenins.