71084-07-6

Usage

Chemical structure

A dodecyl alkyne group attached to a tetrahydro-2H-pyran-2-yloxy group.

Type of compound

Synthetic chemical compound.

Applications

Research and industrial applications.

Potential uses

Pharmaceutical industry, materials science, and chemical synthesis.

Biological activity

May have biological activity and could be used as a building block for the synthesis of more complex molecules.

Unique structure

Its unique structure and properties make it a valuable tool for scientists and researchers in a variety of fields.

Functional groups

Contains alkyne, ether, and tetrahydro-2H-pyran functional groups.

Molecular weight

Approximately 280.45 g/mol (calculated from the molecular formula).

Physical state

Likely a liquid or a low-melting solid at room temperature (based on the presence of a long alkyl chain and an ether group).

Solubility

Expected to be soluble in organic solvents like ethanol, methanol, and dichloromethane due to its nonpolar nature.

Stability

May be sensitive to oxidation and hydrolysis, as it contains an alkyne and an ether group.

Hazards

Potential hazards are not explicitly mentioned in the provided material, but due to its synthetic nature and functional groups, it may have some hazards associated with its handling and use.

Storage

Should be stored in a cool, dry, and well-ventilated area, away from heat and moisture, and protected from light (based on general storage recommendations for similar compounds).

Safety precautions

Safety precautions are not explicitly mentioned in the provided material, but due to its synthetic nature and functional groups, it is advisable to follow standard laboratory safety practices, such as wearing gloves, goggles, and a lab coat, and working in a fume hood when handling 12-(Tetrahydro-2H-pyran-2-yloxy)-1-dodecyne.

InChI:InChI=1/C17H30O2/c1-2-3-4-5-6-7-8-9-10-12-15-18-17-14-11-13-16-19-17/h1,17H,3-16H2

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 18202-10-3 11-dodecyn-1-ol 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 51795-88-1 1-bromo-10-(tetrahydropyranyloxy)decane 
• 74-86-2 acetylene 
• 70277-75-7 lithium acetylide 
• 780773-99-1 11,12-dibromododecyl tetrahydro-2H-2-pyranyl ether 
• 53463-68-6 1-bromo-10-decanol 
• 3344-77-2 12-bromododecanol 
• 96450-84-9 11,12-dibromo-1-dodecanol 
• 41862-94-6 dodec-7-yn-1-ol 
• 2009-84-9 (chloro-6' hexyloxy)-2 tetrahydropyranne 
• 76070-19-4 11-((tetrahydro-2H-pyran-2-yl)oxy)undecanal 
• 76063-02-0 1-(tetrahydropyran-2'-yloxy)-undec-10-ene 

Downstream Products

• 160206-49-5 15-(2-tetrahydropyranyloxy)-2,4-pentadecadiyn-1-ol 
• 71084-06-5 1-(2H-tetrahydropyranyloxy)-11-tetradecyne 
• 34010-15-6 cis-11-tetradecen-1-ol 
• 20711-10-8 (Z)-11-tetradecenyl acetate 
• 62972-93-4 (Z)-octadec-11-en-1-ol 
• 6186-98-7 (Z)-11-octadecen-1-yl acetate 
• 84999-79-1 1-hydroxy octadec 11-yne 
• 4273-95-4 (Z)-11-octadecenal 
• 56683-54-6 (Z)-11-hexadecen-1-ol 
• 65686-49-9 11-hexadecyn-1-ol 
• 1287709-42-5 16-methylheptadec-11-yn-1-ol 
• 1287709-43-6 (Z)-16-methylheptadec-11-en-1-ol 
• 593-50-0 melissyl alcohol 
• 80625-62-3 (11E,13Z)-hexadeca-11,13-dien-1-ol 

Relevant academic research and scientific papers

4,4,16-Trifluoropalmitate: Design, Synthesis, Tritiation, Radiofluorination and Preclinical PET Imaging Studies on Myocardial Fatty Acid Oxidation

Fatty acid oxidation (FAO) produces most of the ATP used to sustain the cardiac contractile work, although glycolysis is a secondary source of ATP under normal physiological conditions. FAO impairment has been reported in the advanced stages of heart failure (HF) and is strongly linked to disease progression and severity. Thus, from a clinical perspective, FAO dysregulation provides prognostic value for HF progression, the assessment of which could be used to improve patient monitoring and the effectiveness of therapy. Positron emission tomography (PET) imaging represents a powerful tool for the assessment and quantification of metabolic pathways in vivo. Several FAO PET tracers have been reported in the literature, but none of them is in routine clinical use yet. Metabolically trapped tracers are particularly interesting because they undergo FAO to generate a radioactive metabolite that is subsequently trapped in the mitochondria, thus providing a quantitative means of measuring FAO in vivo. Herein, we describe the design, synthesis, tritium labelling and radiofluorination of 4,4,16-trifluoro-palmitate (1) as a novel potential metabolically trapped FAO tracer. Preliminary PET-CT studies on [18F]1 in rats showed rapid blood clearance, good metabolic stability – confirmed by using [3H]1 in vitro – and resistance towards defluorination. However, cardiac uptake in rats was modest (0.24±0.04 % ID/g), and kinetic analysis showed reversible uptake, thus indicating that [18F]1 is not irreversibly trapped.

A marine natural product (R, Z) - 24-methyl-twenty-five carbon -16-butene -2,4-diyne -1,6-diol and its antimer synthesis method

The invention relates to a synthetic method of a marine natural product namely (R, Z)-24-methyl-25-carbon-16-butylene-2,4-diyne-1,6-diol and an enantiomer thereof, and belongs to the field of chemical synthesis. The synthetic method comprises the following steps: firstly, preparing long chain alkyl iodide by using a series of simple reactions including bromination, oxidation, esterification, reduction and the like; and then, performing multiple steps of reactions including coupling, dislocation, oxidation, selective reduction, asymmetric alkynylation addition, esterification, hydrolysis and the like by taking propargyl alcohol and the long chain alkyl iodide as starting materials to synthesize the marine natural product namely (R, Z)-24-methyl-25-carbon-16-butylene-2,4-diyne-1,6-diol and the enantiomer thereof, wherein the key step is that trimethylsilylacetylene and alkynal are subjected to asymmetric addition reaction to generate alkynol segments with high optical purity by one step. The synthetic method provided by the invention reports the synthesis of the natural product of the type for the first time, and has the characteristics of simple and convenient steps, relatively high total yield, good product stereoselectivity and the like, and the optical purity of each of the two types of synthesized products is more than 99%ee.

Total Syntheses of (R)-Strongylodiols C and D

The first total syntheses of two marine natural products, (R)-strongylodiols C and D, with 99% ee were achieved. The key steps of the strategy include the zipper reaction of an alkyne, the asymmetric alkynylation of an unsaturated aliphatic aldehyde catalyzed with Trost's ProPhenol ligand, and the Cadiot-Chodkiewicz cross-coupling reaction of a chiral propargylic alcohol with a bromoalkyne.

Catalytic asymmetric synthesis of (S,4E,15Z)-docosa-4,15-dien-1-yn-3-ol, an antitumor marine natural product

Abstract An efficient enantioselective total synthesis of an antitumor marine natural product (S,4E,15Z)-docosa-4,15-dien-1-yn-3-ol 1 with 96% ee and 15% overall yield has been achieved; this is the first preparation of 1 via asymmetric catalytic strategy

First total synthesis and antileishmanial activity of (Z)-16-methyl-11- heptadecenoic acid, a new marine fatty acid from the sponge Dragmaxia undata

The first total synthesis for the (Z)-16-methyl-11-heptadecenoic acid, a novel fatty acid from the sponge Dragmaxia undata, was accomplished in seven steps and in a 44% overall yield. The use of (trimethylsilyl)acetylene was key in the synthesis. Based on a previous developed strategy in our laboratory the best synthetic route towards the title compound was first acetylide coupling of (trimethylsilyl)acetylene to the long-chain protected 10-bromo-1-decanol followed by a second acetylide coupling to the short-chain 1-bromo-4- methylpentane, which resulted in higher yields. Complete spectral data is also presented for the first time for this recently discovered fatty acid and the cis double bond stereochemistry of the natural acid was established. The title compound displayed antiprotozoal activity against Leishmania donovani (IC 50 = 165.5 ± 23.4 μM) and inhibited the leishmania DNA topoisomerase IB enzyme (LdTopIB) with an IC50 = 62.3 ± 0.7 μM.

Odd-numbered very-long-chain polyunsaturated fatty acids from the dinoflagellate Amphidinium carterae identified by atmospheric pressure chemical ionization liquid chromatography-mass spectrometry

A method is described for the enrichment of odd very-long-chain polyunsaturated fatty acids (VLCPUFAs) by means of RP-HPLC and argentation TLC from total fatty acids of the dinoflagellate A. carterae and their identification as picolinyl esters by means of microbore liquid chromatography-mass spectrometry with atmospheric pressure chemical ionization (LC-MS/APCI). The combination of argentation TLC and LC-MS/APCI was used to identify rare and unusual odd VLCPUFAs up to nonacosahexaenoic acid. Two acids, (allZ)-nonacosa-11,14,17,20,23-pentaenoic acid (29:5n-6) and (allZ)-nonacosa-11,14,17,20,23,26-hexaenoic acid (29:6n-3), were synthesized for the first time to unambiguously confirm their structure. Possible biosynthetic pathways for odd VLCPUFAs are also proposed.

Synthesis and biological evaluation of a "natural" insect repellent

(11Z)-11,19-Icosadienyl acetate (1) has been shown to be an efficient repellent against the ant Myrmica rubra whereas its corresponding (11E) stereoisomer 2 does not exhibit any repellent activity at all. Several synthetic strategies for these two compounds have been evaluated.

Synthesis of a natural insect repellent isolated from thrips

A convenient, high yield procedure for the synthesis of (11Z)-11,19-eicosadienyl acetate (1) has been developed. This compound shows strong repellent activity against ants.

Ethynylation of the ether derivatives of ω-haloalkanols with lithium acetylide-ethylenediamide complex

A new operationally simple and highly efficient procedure for the ethynylation of ether derivatives of ω-haloalkanols with lithium acetylide-ethylenediamine complex in N,N-dimethylacetamide is described.

Fluorescence-labeled sphingosines as substrates of sphingosine kinases 1 and 2

Fluorescently labeled D-erythro-sphingosines have been successfully synthesized in 9 and 12 steps starting from commercially available Garner aldehyde. Determining the influence of the nature, position and linkage of the label on the in vitro phosphorylation rate by sphingosine kinases 1 and 2 resulted in the identification of a pyrene- and a NBD-labeled sphingosine which are both phosphorylated with efficiency comparable to the natural substrate.