2H-Pyran, tetrahydro-2-(10-tetradecynyloxy)-

Base Information

• Chemical Name: 2H-Pyran, tetrahydro-2-(10-tetradecynyloxy)-
• CAS No.: 86252-54-2
• Molecular Formula: C19H34O2
• Molecular Weight: 294.478
• Mol file: 86252-54-2.mol

Synonyms:10-Tetradecyn-1-ol THP ether;2H-Pyran,tetrahydro-2-(10-tetradecynyloxy);1-tetrahydropyranyloxy-10-tetradecyne;1-(tetrahydropyran-2'-yloxy)tetradec-10-yne;

Chemical Property of 2H-Pyran, tetrahydro-2-(10-tetradecynyloxy)-

Chemical Property:

• PSA: 18.46000
• LogP: 5.45390

Purity/Quality:

Tetrahydro-2-(10-tetradecyn-1-yloxy)-2H-pyran ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Tetrahydro-2-(10-tetradecyn-1-yloxy)-2H-pyran is an intermediate in the synthesis of cyclopropyl containing fatty acids as mechanistic probes for cytochromes P450.

Technology Process of 2H-Pyran, tetrahydro-2-(10-tetradecynyloxy)-

There total 7 articles about 2H-Pyran, tetrahydro-2-(10-tetradecynyloxy)- 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: 81.0%

1-[(tetrahydropyran-2-yl)oxy]undec-10-yne (51953-88-9,151329-50-9) + propyl bromide (106-94-5) → 1-(tetrahydropyran-2'-yloxy)tetradec-10-yne (86252-54-2)

Guidance literature:

1-[(tetrahydropyran-2-yl)oxy]undec-10-yne; With n-butyllithium; In tetrahydrofuran; at -40 ℃; for 2h;

propyl bromide; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at -40 - 20 ℃;

DOI:10.1021/jo047985d

Reference yield:

9-bromononan-1-ol (55362-80-6) → 1-(tetrahydropyran-2'-yloxy)tetradec-10-yne (86252-54-2)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH / diethyl ether

2: 1.) 2M BuLi / 1.) hexane, HMPT, 0 deg C, 30 min, 2.)THF, r. t., 12 h

With n-butyllithium; toluene-4-sulfonic acid; In diethyl ether;

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → 1-(tetrahydropyran-2'-yloxy)tetradec-10-yne (86252-54-2)

Guidance literature:

Multi-step reaction with 2 steps

1: p-TsOH / diethyl ether

2: 1.) 2M BuLi / 1.) hexane, HMPT, 0 deg C, 30 min, 2.)THF, r. t., 12 h

With n-butyllithium; toluene-4-sulfonic acid; In diethyl ether;

upstream raw materials:

2-(9-bromononyloxy)tetrahydropyran

1-Pentyne

1-[(tetrahydropyran-2-yl)oxy]undec-10-yne

propyl bromide

Downstream raw materials:

Z,Z-3,14-octadecadien-1-ol acetate

Refernces

• 1、 Ahn, Jong-Woong,Ahn, Mi-Ja,Zee, Ok-Pyo,Kim, Eun-Joo,Lee, Sueg-Geun,et al.. "PIPERIDINE ALKALOIDS FROM PIPER RETROFRACTUM FRUITS". . p. 3609 - 3612. Retrieved 2007/10/02.
• 2、 Rossi, Renzo,Carpita, Adriano,Gaudenzi, Loretta,Quirici, Maria Grazia. "INSECT SEX PHEROMONES. STEREOSELECTIVE SYNTHESIS OF SEVERAL (Z)- AND (E)-ALKEN-1-OLS, THEIR ACETATES, AND OF (9Z,12E)-9,12-TETRADECADIEN-1-YL ACETATE". . p. 237 - 246. Retrieved 2007/10/02.