51953-88-9

Basic information

• Product Name: 11-(Tetrahydro-2H-pyran-2-yloxy)-1-undecyne
• Synonyms: 11-(Tetrahydro-2H-pyran-2-yloxy)-1-undecyne;2-[(10-Undecynyl)oxy]tetrahydro-2H-pyran;Tetrahydro-2-(10-undecynyloxy)-2H-pyran
• CAS NO: 51953-88-9
• Molecular Formula: C₁₆H₂₈O₂
• Molecular Weight: 252.3923
• Mol File: 51953-88-9.mol

Chemical Properties

• Boiling Point: 338°Cat760mmHg
• Flash Point: 114.6°C
• Appearance: /
• Density: 0.92g/cm³
• Vapor Pressure: 0.000198mmHg at 25°C
• Refractive Index: 1.467
• CAS DataBase Reference: 11-(Tetrahydro-2H-pyran-2-yloxy)-1-undecyne(CAS DataBase Reference)
• NIST Chemistry Reference: 11-(Tetrahydro-2H-pyran-2-yloxy)-1-undecyne(51953-88-9)
• EPA Substance Registry System: 11-(Tetrahydro-2H-pyran-2-yloxy)-1-undecyne(51953-88-9)

Safety Data

• Hazardous Substances Data: 51953-88-9(Hazardous Substances Data)

Usage

Chemical structure

A 1-undecyne chain with a tetrahydro-2H-pyran-2-yloxy functional group attached at the 11th carbon position.

Functional groups

Tetrahydro-2H-pyran-2-yloxy, alkyne, and alkane.

Molecular weight

Approximately 268 g/mol.

Physical state

Likely a liquid or a low melting point solid at room temperature.

Solubility

Soluble in organic solvents such as ethanol, methanol, and dichloromethane.

Reactivity

Can undergo various chemical reactions, such as electrophilic addition, nucleophilic addition, and substitution reactions.

Organic synthesis

As a building block for creating various other organic molecules.

Pharmaceutical intermediate

Used in the synthesis of pharmaceutical compounds.

Agrochemical ingredient

Potentially used in the development of agrochemicals.

Specialty chemicals

Used in the production of specialty chemicals.

Research value

Its unique structure and reactivity make it a valuable tool for studying chemical reactions and mechanisms in the laboratory.

Versatility

Diverse potential uses in the field of chemistry.

Safety precautions

As with any chemical compound, it is essential to follow proper safety protocols, such as wearing gloves, goggles, and a lab coat, and working in a well-ventilated area or fume hood when handling 11-(Tetrahydro-2H-pyran-2-yloxy)-1-undecyne.

InChI:InChI=1/C16H28O2/c1-2-3-4-5-6-7-8-9-11-14-17-16-13-10-12-15-18-16/h1,16H,3-15H2

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 2774-84-7 undec-10-yn-1-ol 
• 209474-42-0 11-(trimethylsilyl)-1-[(tetrahydropyran-2-yl)oxy]undec-10-yne 
• 5390-04-5 pent-1-yn-5-ol 
• 34683-71-1 undec-2-yn-1-ol 
• 112-43-6 10-Undecen-1-ol 
• 3937-56-2 1,9-Nonanediol 
• 54377-35-4 undec-4-yn-1-ol 
• 3003-84-7 Tetrahydrofurfuryl chloride 
• 2777-66-4 methyl 10-undecynoate 
• 111-81-9 Methyl 10-undecenoate 
• 54299-09-1 3-n-undecyn-1-ol 
• 3452-09-3 1-nonyne 
• 112-38-9 10-undecenoic acid 

Downstream Products

• 544476-91-7 (S)-3-Benzyl-4-[12-(tetrahydro-pyran-2-yloxy)-dodec-2-ynoyl]-oxazolidin-2-one 
• 832726-23-5 phenyl 4-(4-butoxyphenylsulfanyl)-2'-[1-hydroxy-12-(tetrahydro-2H-pyran-2-yloxy)dodec-2-ynyl]biphenyl-3-sulfonate 
• 86252-66-6 Z,Z-3,14-octadecadien-1-ol acetate 
• 86252-67-7 Z,Z-4,15-octadecadien-1-ol acetate 
• 86252-65-5 (2Z,13Z)-2,13-octadecadienyl acetate 
• 86252-74-6 (2E,13Z)-octadeca-2,13-dienyl acetate 
• 765-17-3 (10E,12E)-Hexadeca-10,12-dien-1-ol 
• 765-17-3 (10E,12Z)-hexadeca-10,12-dien-1-ol 
• 173473-54-6 6-(10-Heptadecynyl)-2-methoxybenzoic acid 
• 173473-56-8 6-<(Z)-10-Heptadecenyl>-2-methoxybenzoic acid 
• 173473-42-2 Methyl 6-(9-acetoxynonyl)-2-methoxybenzoate 
• 173473-53-5 2-Methoxy-6-(10-pentadecynyl)benzoic acid 

Relevant articles and documents

Preparation method of (E,E,Z)-10, 12, 14-hexadecatriene acetate, composition and attractant core

The invention relates to a preparation method of (E,E,Z)-10,12,14-hexadecatriene acetate, a Diaphania pyloalis attractant composition and an attractant core, and compared with the prior art, the preparation method of (E,E,Z)-10,12,14-hexadecatriene acetate has the advantages of cheap and easily available raw materials, high reaction yield, simple post-treatment, high isomerization purity of the synthesized compound, clean and environment-friendly process flow, and high activity in field. The Diaphania pyloalis attractant composition based on the (E,E,Z)-10,12,14-hexadecatriene acetate and theattractant core of the Diaphania pyloalis attractant composition have a remarkable moth-luring synergistic effect and can be stably and efficiently used for population monitoring, prevention and control of mulberry borers.

Asymmetric Total Synthesis of Distaminolyne A and Revision of Its Absolute Configuration

The first total synthesis of a marine derived polyacetylene, distaminolyne A, and its enantiomer were achieved from the commercially available undec-10-en-1-ol. A key proline-catalyzed asymmetric α-aminooxylation of an aldehyde intermediate was used to in

First total syntheses of (Z)-15-methyl-10-hexadecenoic acid and the (Z)-13-methyl-8-tetradecenoic acid

The first total syntheses for the (Z)-15-methyl-10-hexadecenoic acid and the (Z)-13-methyl-8-tetradecenoic acid were accomplished in seven steps and in 31-32% overall yields. The (trimethylsilyl)acetylene was the key reagent in both syntheses. It is proposed that the best synthetic strategy towards monounsaturated iso methyl-branched fatty acids with double bonds close to the ω end of the acyl chain is first acetylide coupling of (trimethylsilyl)acetylene to a long-chain bifunctional bromoalkane followed by a second acetylide coupling to a short-chain iso bromoalkane, since higher yields are thus obtained. Spectral data is also presented for the first time for these two unusual fatty acids with potential as biomarkers and as topoisomerase I inhibitors.

Synthesis and SAR studies of a novel class of S1P1 receptor antagonists

A series of Sodium 4-[(4-butoxyphenyl)thio]-2′-substituted-1,1′-biphenyl-3- sulfonates were identified as functional sphingosine-1-phosphate (S1P) antagonists with selectivity for the S1P1 receptor subtype starting from chemical lead 2, which w

Synthetic pheromone compositions

The present invention provides compounds useful for preparing synthetic pheromone compositions that can be used as attractants or inhibitors of insect species. The compositions are useful in the control of navel orangeworm or meal moth insect pests.

Synthesis of fluorescence-labeled sphingosine and sphingosine 1-phosphate; Effective tools for sphingosine and sphingosine 1-phosphate behavior

A fluorescence-labeled sphingosine and sphingosine 1-phosphate have been successfully synthesized from the oxazolidinone methyl ester derived from glycidol via monoalkylation and the stereoselective reduction of the resulting ketone. The labeled sphingosine was converted into its phosphate by treatment with sphingosine kinase 1 (SPHK1) from mouse, and in platelets, and it was incorporated into the Chinese Hamster Ovarian (CHO) cells. In addition, MAPK was activated by NBD-Sph-1-P through Edg-1, Sph-1-P receptor.

An Efficient Derivation of the Versatile Chiron Antipode 1-tert-Butyldimethylsilylpenta-1,4-diyn-3-ol: Application to the Synthesis of (15E,R,R)-Duryne

The title chiron, 1-tert-butyldimethylsilylpenta-1,4-diyn-3-ol (5), an essential segment of various bioactive polyacetylenic alcohols, has been efficiently resolved via a lipase-catalyzed acylation strategy. Lipases from different Pseudomonas species and Candida rugosa (CRL) furnished its (S)-antipode (as esters) with 86-96% ee. However, the (R)-alcohol 5 could be prepared with acceptable enantiomeric purity (93% ee) only using CRL-vinyl acetate-diisopropyl ether as the reagent protocol and under double filtration conditions. The chiron alcohol was then extended to the target compound (15E,R,R)-duryne (I) by its pyranylation, alkylation with the required achiral C20-α,ω-dibromide 15, and suitable functionalization.

Modified bile acids process for their preparation and their use

The invention relates to linker-modified bile acid derivatives of the formula I: STR1 wherein the radicals X1, X2, X3 and Y and n are as defined in the claims, and to a process for their preparation. The compounds according to the invention are therapeutically active and are thus suitable as drugs, especially as hypolipldemics. The invention further relates to the use of the bile acid derivatives according to the invention as drugs.

Synthesis of dodec-10E-Enyl acetate - The sex pheromone of phyllonorycter blancardella (Lepidoptera: Gracillariidae)

Dodec-10E-enyl acetate has been synthesized from undecenoic acid. Field trials have shown its high attractiveness for Phyllonorycter blancardella males. 1996 Plenum Publishing Corporation.

Synthesis of Anacardic Acids

The anacardic acids 1-11, isolated from various plants, were synthesized by a new general method.Reaction of the methyl alkynoates 12-18 with 1-methoxy-1,4-cyclohexadiene at 200 deg C afforded directly the methyl 2-methoxybenzoates 19-25 with long chain substituents in 6-position in 74-85percent yield.The dienophiles 12-16 were prepared by pyrolysis of the corresponding acylphosphoranes 26-30, the dienophiles 17 and 18 by methoxycarbonylation of the corresponding alkynes 31 and 32 via the hydroxy esters 33 and 34.Demethylation of 19-23 with AlI3 gave the methyl salicylates 35-39 which could be hydrolized to the anacardic acids 1-4 and 7.Hydrolysis of 24 and 25 provided the hydroxy acids 40 and 41, which were converted by treatment with CBr4/PPh3 into the acids 42 and 43 bearing bromoalkyl side chains.These were transformed into 44-47 by reaction with 1-hexynyllithium and 1-octynyllithium.Stereoselective hydrogenation of 44-47 gave 48-51 with (Z)-alkene side chains.In a similar approach 42 was converted into 52 and then into 53, which gave upon treatment with 1-pentynylmagnesium bromide or 1-heptynylmagnesium bromide the acids 54 and 55 with alkadiyne side chains.Stereoselective hydrogenation provided 56 and 57 with (Z,Z)-alkadiene side chains.The 2-methoxy group in 48-51, 56, 57 was demethylated by treatment with AlI3 to give the anacardic acids 5, 6, 8-11. - Keywords: Anacardic acids; Benzoates, methyl 6-alkyl-2-methoxy-; 2-Alkynoates, methyl; Aluminium triiodide, demethylation by treatment with