4-(1-Propynyl)-1-(5-hexene-1,3-diynyl)-1,4-cyclohexanediol

Base Information

• Chemical Name: 4-(1-Propynyl)-1-(5-hexene-1,3-diynyl)-1,4-cyclohexanediol
• CAS No.: 147196-75-6
• Molecular Formula: C₁₅H₁₆O₂
• Molecular Weight: 228.291
• Mol file: 147196-75-6.mol

Synonyms:

Chemical Property of 4-(1-Propynyl)-1-(5-hexene-1,3-diynyl)-1,4-cyclohexanediol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(1-Propynyl)-1-(5-hexene-1,3-diynyl)-1,4-cyclohexanediol

There total 7 articles about 4-(1-Propynyl)-1-(5-hexene-1,3-diynyl)-1,4-cyclohexanediol 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:

4-(1-Propynyl)-1-(4-(trimethylsilyl)-1,3-butadiynyl)-1,4-cyclohexanediol → 4-(1-Propynyl)-1-(5-hexene-1,3-diynyl)-1,4-cyclohexanediol (147196-75-6)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature

2: 1) palladium⁽⁰⁾ tetrakistriphenylphosphine / 1) toluene, room temp., 30 min, 2) room temp., 4 h

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1021/jo00060a057

Reference yield:

4-Hydroxy-1-(4-(trimethylsilyl)-1,3-butadiynyl)cyclohexanol (147196-68-7) → 4-(1-Propynyl)-1-(5-hexene-1,3-diynyl)-1,4-cyclohexanediol (147196-75-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / oxalyl chloride, DMSO / tetrahydrofuran / 0.25 h / -60 - -50 °C

2: 98 percent / PPTS / CH₂Cl₂ / 4 h / Ambient temperature

3: 1) butyllithium / 1) THF, a) -78 deg C, 30 min, b) room temp., 3 h, 2) THF, a) 0 deg C, 30 min, b) room temp., 7 h

4: PPTS / ethanol / 7 h / Heating

5: tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature

6: 1) palladium⁽⁰⁾ tetrakistriphenylphosphine / 1) toluene, room temp., 30 min, 2) room temp., 4 h

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; dimethyl sulfoxide; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/jo00060a057

Reference yield:

4-Hydroxy-4-(4-(trimethylsilyl)-1,3-butadiynyl)-1-cyclohexanone (147196-70-1) → 4-(1-Propynyl)-1-(5-hexene-1,3-diynyl)-1,4-cyclohexanediol (147196-75-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / PPTS / CH₂Cl₂ / 4 h / Ambient temperature

2: 1) butyllithium / 1) THF, a) -78 deg C, 30 min, b) room temp., 3 h, 2) THF, a) 0 deg C, 30 min, b) room temp., 7 h

3: PPTS / ethanol / 7 h / Heating

4: tetrabutylammonium fluoride / tetrahydrofuran / 3 h / Ambient temperature

5: 1) palladium⁽⁰⁾ tetrakistriphenylphosphine / 1) toluene, room temp., 30 min, 2) room temp., 4 h

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/jo00060a057

upstream raw materials:

Vinyl bromide

4-Hydroxy-4-(4-(trimethylsilyl)-1,3-butadiynyl)-1-cyclohexanone

4-Hydroxy-1-(4-(trimethylsilyl)-1,3-butadiynyl)cyclohexanol

4-(2-Tetrahydropyranyloxy)-1-(4-(trimethylsilyl)-1,3-butadiynyl)cyclohexanol