2-(Oct-7-yn-1-yloxy)tetrahydropyran

Base Information

• Chemical Name: 2-(Oct-7-yn-1-yloxy)tetrahydropyran
• CAS No.: 16695-31-1
• Deprecated CAS: 158576-21-7
• Molecular Formula: C13H22 O2
• Molecular Weight: 210.316
• Hs Code.: 2932999099
• European Community (EC) Number: 240-740-3
• DSSTox Substance ID: DTXSID70275829,DTXSID60884929
• Nikkaji Number: J236.822F
• Mol file: 16695-31-1.mol

Synonyms:2-(Oct-7-yn-1-yloxy)tetrahydropyran;2-oct-7-ynoxyoxane;16695-31-1;Tetrahydro-2-(7-octyn-1-yloxy)-2H-pyran;EINECS 240-740-3;Tetrahydro-2-(7-octynyloxy)-2H-pyran;2H-Pyran, tetrahydro-2-(7-octynyloxy)-;2H-Pyran, tetrahydro-2-(7-octyn-1-yloxy)-;SCHEMBL6819838;DTXSID60884929;DTXSID70275829;8-(tetrahydropyranyloxy)-1-octyne;1-(tetrahydropyranyloxy)-oct-7-yne;AT23229;5-tetrahydropyranyloxypropanyl-1-pentyne;8-[(Tetrahydropyran-2-yl)oxy]-1-octyne;2-(OCT-7-YN-1-YLOXY)TETRAHYDRO-2H-PYRAN;J-010325;158576-21-7

Chemical Property of 2-(Oct-7-yn-1-yloxy)tetrahydropyran

Chemical Property:

• Vapor Pressure: 0.00197mmHg at 25°C
• Boiling Point: 300.7°C at 760 mmHg
• Flash Point: 108.5°C
• PSA: 18.46000
• Density: 0.94g/cm³
• LogP: 3.11330
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 210.161979940
• Heavy Atom Count: 15
• Complexity: 192

Purity/Quality:

99% ^*data from raw suppliers

Tetrahydro-2-(7-octyn-1-yloxy)-2H-pyran ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CCCCCCCOC1CCCCO1
• 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.

Technology Process of 2-(Oct-7-yn-1-yloxy)tetrahydropyran

There total 23 articles about 2-(Oct-7-yn-1-yloxy)tetrahydropyran which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

3,4-dihydro-2H-pyran (110-87-2) + oct-7-yn-1-ol (871-91-0) → 1-(2-Tetrahydropyranyloxy)-7-octyne (16695-31-1)

Guidance literature:

camphor-10-sulfonic acid; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo0110146

Reference yield: 98.0%

(chloro-6' hexyloxy)-2 tetrahydropyranne (2009-84-9) + lithium acetylide-ethylenediamine complex (1216963-74-4) → 1-(2-Tetrahydropyranyloxy)-7-octyne (16695-31-1)

Guidance literature:

In dimethyl sulfoxide; at 20 ℃; for 3h;

DOI:10.1002/jccs.199900011

Reference yield: 91.0%

2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran (53963-10-3) + trimethylsilylacetylene (1066-54-2) → 1-(2-Tetrahydropyranyloxy)-7-octyne (16695-31-1)

Guidance literature:

trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; cyclohexane; at -60 - 0 ℃; for 0.5h;

2-[(6-bromohexyl)oxy]tetrahydro-2H-pyran; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; cyclohexane; at -20 - 20 ℃; for 19h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 48h;

DOI:10.1016/j.bmc.2013.05.013

upstream raw materials:

3,4-dihydro-2H-pyran

oct-7-yn-1-ol

(chloro-6' hexyloxy)-2 tetrahydropyranne

lithium acetylide-ethylenediamine complex

Downstream raw materials:

(7E)-1-(tetrahydropyran-2'-yloxy)-7-dodecene

(E)-7-Decen-1-ol

(E)-7-decenyl acetate

8-tetrahydropyranyloxy-2-trimethylstannyl-1-octene

Refernces

• 1、 Sonnet. "A practical synthesis of the sex pheromone of the pink bollworm". . p. 3793 - 3794. Retrieved 1974.
• 2、 -. "A (Z, Z, E) - 7, 11, 13 - sixteen carbon three activated olefinic ketones synthesis method (by machine translation)". Page/Page column 2; 3; 8; 11. . Retrieved 2018/07/15.
• 3、 Marshall, Andrew J.,Lin, Jian-Ming,Grey, Andrew,Reid, Ian R.,Cornish, Jillian,Denny, William A.. "Long-chain triazolyl acids as inhibitors of osteoclastogenesis". . p. 4112 - 4119. Retrieved 2013/07/27.