trans-(12S)-methyl-1-oxacyclododec-9-ene-2-one

Base Information

Chemical Name:trans-(12S)-methyl-1-oxacyclododec-9-ene-2-one
CAS No.:59780-27-7
Molecular Formula:C₁₂H₂₀O₂
Molecular Weight:196.29
Hs Code.:

Synonyms:

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Chemical Property of trans-(12S)-methyl-1-oxacyclododec-9-ene-2-one

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Technology Process of trans-(12S)-methyl-1-oxacyclododec-9-ene-2-one

There total 7 articles about trans-(12S)-methyl-1-oxacyclododec-9-ene-2-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:

: exo-9-((R)-2-hydroxypropyl)bicyclo[6.1.0]nonan-1-ol

: 59780-27-7
trans-(12S)-methyl-1-oxacyclododec-9-ene-2-one

: 59780-28-8
(+)-recifeiolide

Guidance literature:: With bis-[(trifluoroacetoxy)iodo]benzene; In dichloromethane; for 0.25h; Overall yield = 76 %;
DOI:10.1016/j.tet.2014.03.032

Reference yield:

: 502-49-8
cycloactanone

: 59780-27-7
trans-(12S)-methyl-1-oxacyclododec-9-ene-2-one

: 59780-28-8
(+)-recifeiolide

Guidance literature:: Multi-step reaction with 7 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.58 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / benzene / Reflux

3.1: hydrogen iodide / benzene

4.1: triisopropoxytitanium(IV) chloride; zinc / tetrahydrofuran / Inert atmosphere

5.1: triethylamine / tetrahydrofuran / 0 °C

6.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; water / 1 h / 20 °C

7.1: bis-[(trifluoroacetoxy)iodo]benzene / dichloromethane / 0.25 h

With triisopropoxytitanium(IV) chloride; palladium 10% on activated carbon; hydrogen iodide; hydrogen; toluene-4-sulfonic acid; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; zinc; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; benzene;
DOI:10.1016/j.tet.2014.03.032

Reference yield:

: 1601479-35-9
C₁₉H₂₈O₃

: 59780-27-7
trans-(12S)-methyl-1-oxacyclododec-9-ene-2-one

: 59780-28-8
(+)-recifeiolide

Guidance literature:: Multi-step reaction with 6 steps

1: toluene-4-sulfonic acid / benzene / Reflux

2: hydrogen iodide / benzene

3: triisopropoxytitanium(IV) chloride; zinc / tetrahydrofuran / Inert atmosphere

4: triethylamine / tetrahydrofuran / 0 °C

5: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; water / 1 h / 20 °C

6: bis-[(trifluoroacetoxy)iodo]benzene / dichloromethane / 0.25 h

With triisopropoxytitanium(IV) chloride; palladium 10% on activated carbon; hydrogen iodide; hydrogen; toluene-4-sulfonic acid; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; zinc; In tetrahydrofuran; dichloromethane; water; benzene;
DOI:10.1016/j.tet.2014.03.032