(E)-Tetrahydro-2-(11-tetradecen-9-ynyloxy)-2H-pyran

Base Information

• Chemical Name: (E)-Tetrahydro-2-(11-tetradecen-9-ynyloxy)-2H-pyran
• CAS No.: 54664-77-6
• Molecular Formula: C19H32 O2
• Molecular Weight: 292.462
• Hs Code.: 2932999099
• European Community (EC) Number: 259-285-7
• DSSTox Substance ID: DTXSID00886109
• Nikkaji Number: J326.668K
• Mol file: 54664-77-6.mol

Synonyms:54664-77-6;EINECS 259-285-7;(E)-Tetrahydro-2-(11-tetradecen-9-ynyloxy)-2H-pyran;(E)-2-(11-Tetradecen-9-yn-1-yloxy)tetrahydropyran;2H-Pyran, tetrahydro-2-((11E)-11-tetradecen-9-ynyloxy)-;2H-Pyran, tetrahydro-2-[(11E)-11-tetradecen-9-ynyloxy]-;2H-Pyran, tetrahydro-2-((11E)-11-tetradecen-9-yn-1-yloxy)-;2H-Pyran, tetrahydro-2-[(11E)-11-tetradecen-9-yn-1-yloxy]-;DTXSID00886109;Tetrahydro-2-[(E)-11-tetradecen-9-ynyloxy]-2H-pyran;2H-Pyran, tetrahydro-2-(11-tetradecen-9-ynyloxy)-, (E)-

Chemical Property of (E)-Tetrahydro-2-(11-tetradecen-9-ynyloxy)-2H-pyran

Chemical Property:

• Vapor Pressure: 1.94E-06mmHg at 25°C
• Boiling Point: 406.2°C at 760 mmHg
• Flash Point: 139.7°C
• PSA: 18.46000
• Density: 0.93g/cm³
• LogP: 5.22990
• XLogP3: 6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 10
• Exact Mass: 292.240230259
• Heavy Atom Count: 21
• Complexity: 321

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CC#CCCCCCCCCOC1CCCCO1
• Isomeric SMILES: CC/C=C/C#CCCCCCCCCOC1CCCCO1

Technology Process of (E)-Tetrahydro-2-(11-tetradecen-9-ynyloxy)-2H-pyran

There total 7 articles about (E)-Tetrahydro-2-(11-tetradecen-9-ynyloxy)-2H-pyran 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:

2-(8-bromooctyloxy)tetrahydropyran (50816-20-1) → (E)-1-tetradec-2-en-4-yn (54664-77-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / LiNH₂

2: 80 percent / pyridinium dichromate (PDC) / CH₂Cl₂

3: 1.) LiBr, n-BuLi, 3.) n-BuLi

With dipyridinium dichromate; n-butyllithium; lithium amide; lithium bromide; In dichloromethane;

Reference yield:

11-(tetrahydro-2H-pyran-2-yloxy)undec-2-yn-1-ol (87242-02-2) → (E)-1-tetradec-2-en-4-yn (54664-77-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / pyridinium dichromate (PDC) / CH₂Cl₂

2: 1.) LiBr, n-BuLi, 3.) n-BuLi

With dipyridinium dichromate; n-butyllithium; lithium bromide; In dichloromethane;

Reference yield:

2-(8-bromooctyloxy)tetrahydropyran (50816-20-1) → (E)-1-tetradec-2-en-4-yn (54664-77-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) lithium amide / 1.) liq. ammonia, 2 h, 2.) THF, -33 deg C, 6 h

2: 65 percent / triphenylphosphine, carbon tetrachloride / 6 h / Heating

3: 1.) CuI / 1.) ether, room temperature, 1 h, 2.) THF, 4 h, room temperature

With tetrachloromethane; copper(l) iodide; lithium amide; triphenylphosphine;

upstream raw materials:

methyl magnesium iodide

(E)-13-<(tetrahydro-2H-pyran-2-yl)-oxy>-1-chlorotridec-2-en-4-yn

n-propyltriphenylphosphonium bromide

11-(2'-tetrahydropyranyloxy)-2-undecyl-1-al

Downstream raw materials:

(E)-tetradec-9-yn-11-en-1-ol

Refernces

• 1、 Yadav, J S,Deshpande, Prasad K,Reddy, E Rajarathnam. "PREPARATION OF 1,3-DIENES, ITS APPLICATION TO THE SYNTHESIS OF (Z,E)-9,11-TETRADECADIENYL ACETATE AND (E,E)-10,12-HEXADECADIENAL: SEX PHEROMONES OF COTTON PESTS". . p. 125 - 134. Retrieved 2007/10/02.