(R)-6-(4-(hept-6-en-1-ynyl)phenyl)-3a,4-dihydro-1H-cyclopenta[c]furan-5(3H)-one

Base Information

Chemical Name:(R)-6-(4-(hept-6-en-1-ynyl)phenyl)-3a,4-dihydro-1H-cyclopenta[c]furan-5(3H)-one
CAS No.:1326218-24-9
Molecular Formula:C₂₀H₂₀O₂
Molecular Weight:292.378
Hs Code.:

Synonyms:(R)-6-(4-(hept-6-en-1-ynyl)phenyl)-3a,4-dihydro-1H-cyclopenta[c]furan-5(3H)-one

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Chemical Property of (R)-6-(4-(hept-6-en-1-ynyl)phenyl)-3a,4-dihydro-1H-cyclopenta[c]furan-5(3H)-one

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Technology Process of (R)-6-(4-(hept-6-en-1-ynyl)phenyl)-3a,4-dihydro-1H-cyclopenta[c]furan-5(3H)-one

There total 7 articles about (R)-6-(4-(hept-6-en-1-ynyl)phenyl)-3a,4-dihydro-1H-cyclopenta[c]furan-5(3H)-one 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:

: 201230-82-2
carbon monoxide

: 1326218-16-9
1-(3-(allyloxy)prop-1-ynyl)-4-(hept-6-en-1-ynyl)benzene

: 1326218-24-9
(R)-6-(4-(hept-6-en-1-ynyl)phenyl)-3a,4-dihydro-1H-cyclopenta[c]furan-5(3H)-one

: (S)-6-(4-(hept-6-en-1-ynyl)phenyl)-3a,4-dihydro-1H-cyclopenta[c]furan-5(3H)-one

Guidance literature:: With (R)-(+)-2,2'-bis[bis(3,5-dimethylphenyl)phosphino]-1,1'-binaphthyl; di(rhodium)tetracarbonyl dichloride; silver trifluoromethanesulfonate; In tetrahydrofuran; at 35 ℃; under 760.051 Torr; optical yield given as %ee; enantioselective reaction;
DOI:10.1002/asia.201100271

Reference yield:

: 1326218-62-5
6-(4-iodophenyl)hex-5-ynyl benzoate

: 1326218-24-9
(R)-6-(4-(hept-6-en-1-ynyl)phenyl)-3a,4-dihydro-1H-cyclopenta[c]furan-5(3H)-one

: (S)-6-(4-(hept-6-en-1-ynyl)phenyl)-3a,4-dihydro-1H-cyclopenta[c]furan-5(3H)-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium hydroxide / tetrahydrofuran; methanol / 1 h / 20 °C

2.1: pyridinium chlorochromate / MC / 2 h / 20 °C

3.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

3.2: 3 h / -78 - 20 °C / Inert atmosphere

4.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / tetrahydrofuran / 5 h / 60 °C

5.1: (R)-(+)-2,2'-bis[bis(3,5-dimethylphenyl)phosphino]-1,1'-binaphthyl; di(rhodium)tetracarbonyl dichloride; silver trifluoromethanesulfonate / tetrahydrofuran / 35 °C / 760.05 Torr

With (R)-(+)-2,2'-bis[bis(3,5-dimethylphenyl)phosphino]-1,1'-binaphthyl; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; di(rhodium)tetracarbonyl dichloride; silver trifluoromethanesulfonate; triethylamine; pyridinium chlorochromate; sodium hydroxide; In tetrahydrofuran; methanol; MC; 5.1: Pauson-Khand-type reaction;
DOI:10.1002/asia.201100271

Reference yield:

: 1326218-63-6
6-(4-iodophenyl)hex-5-yn-1-ol

: 1326218-24-9
(R)-6-(4-(hept-6-en-1-ynyl)phenyl)-3a,4-dihydro-1H-cyclopenta[c]furan-5(3H)-one

: (S)-6-(4-(hept-6-en-1-ynyl)phenyl)-3a,4-dihydro-1H-cyclopenta[c]furan-5(3H)-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: pyridinium chlorochromate / MC / 2 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

2.2: 3 h / -78 - 20 °C / Inert atmosphere

3.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine / tetrahydrofuran / 5 h / 60 °C

4.1: (R)-(+)-2,2'-bis[bis(3,5-dimethylphenyl)phosphino]-1,1'-binaphthyl; di(rhodium)tetracarbonyl dichloride; silver trifluoromethanesulfonate / tetrahydrofuran / 35 °C / 760.05 Torr

With (R)-(+)-2,2'-bis[bis(3,5-dimethylphenyl)phosphino]-1,1'-binaphthyl; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; di(rhodium)tetracarbonyl dichloride; silver trifluoromethanesulfonate; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; MC; 4.1: Pauson-Khand-type reaction;
DOI:10.1002/asia.201100271