4,6-Methanocyclopenta[b]pyran-2(3H)-one,hexahydro-5-hydroxy-4a,5-dimethyl-,(4S,4aS,5R,6R,7aS)-(9CI)

Base Information

Chemical Name:4,6-Methanocyclopenta[b]pyran-2(3H)-one,hexahydro-5-hydroxy-4a,5-dimethyl-,(4S,4aS,5R,6R,7aS)-(9CI)
CAS No.:744208-15-9
Molecular Formula:C₁₁H₁₆O₃
Molecular Weight:196.246
Hs Code.:
Mol file:744208-15-9.mol

Synonyms:4,6-Methanocyclopenta[b]pyran-2(3H)-one,hexahydro-5-hydroxy-4a,5-dimethyl-,(4S,4aS,5R,6R,7aS)-(9CI)

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 4,6-Methanocyclopenta[b]pyran-2(3H)-one,hexahydro-5-hydroxy-4a,5-dimethyl-,(4S,4aS,5R,6R,7aS)-(9CI)

Chemical Property:

PSA：46.53000
LogP:1.09900

Purity/Quality:

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Technology Process of 4,6-Methanocyclopenta[b]pyran-2(3H)-one,hexahydro-5-hydroxy-4a,5-dimethyl-,(4S,4aS,5R,6R,7aS)-(9CI)

There total 12 articles about 4,6-Methanocyclopenta[b]pyran-2(3H)-one,hexahydro-5-hydroxy-4a,5-dimethyl-,(4S,4aS,5R,6R,7aS)-(9CI) 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:

: 744207-83-8
(1R,2S,4R,6S)-[4-acetyl-1-methyl-7-oxabicyclo[4.1.0]hept-2-yl]acetic acid methyl ester

: 744208-15-9,744208-27-3
(1S,5S,7R,8R,9S)-8,9-dimethyl-3-oxo-2-oxatricyclo[5.2.1.0^5,9]decan-8-ol

: 744208-15-9,744208-27-3
(1S,5S,7R,8S,9S)-8,9-dimethyl-3-oxo-2-oxatricyclo[5.2.1.0^5,9]decan-8-ol

: methyl [(1S,3S,5R)-5-acetyl-3-hydroxy-2-methylenecyclohexyl]acetate

Guidance literature:: With titanocene dichloride; zinc; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/jo049358u

Reference yield:

: 744207-83-8
(1R,2S,4R,6S)-[4-acetyl-1-methyl-7-oxabicyclo[4.1.0]hept-2-yl]acetic acid methyl ester

: 744208-15-9,744208-27-3
(1S,5S,7R,8R,9S)-8,9-dimethyl-3-oxo-2-oxatricyclo[5.2.1.0^5,9]decan-8-ol

: 744208-15-9,744208-27-3
(1S,5S,7R,8S,9S)-8,9-dimethyl-3-oxo-2-oxatricyclo[5.2.1.0^5,9]decan-8-ol

: methyl [(1S,3S,5R)-5-acetyl-3-hydroxy-2-methylenecyclohexyl]acetate

Guidance literature:: With titanocene dichloride; zinc; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/jo049358u

Reference yield:

: 2102-58-1,22567-18-6,20307-86-2
(+)-trans-carveol

: 744208-15-9,744208-27-3
(1S,5S,7R,8R,9S)-8,9-dimethyl-3-oxo-2-oxatricyclo[5.2.1.0^5,9]decan-8-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: propionic acid / 17 h / 100 - 135 °C

1.2: HCl / H₂O; ethyl acetate

1.3: 13.4 g / KOH / methanol; H₂O / 2 h / Heating

2.1: 86 percent / N-bromosuccinimide / acetone / 0.5 h / 20 °C

3.1: 98 percent / K₂CO₃ / 1 h / Heating

4.1: O₃ / CH₂Cl₂ / 0.25 h / -78 °C

4.2: 82 percent / Ph₃P / CH₂Cl₂ / -78 - 20 °C

5.1: titanocene dichloride; zinc / tetrahydrofuran / 20 °C

With N-Bromosuccinimide; titanocene dichloride; potassium carbonate; ozone; propionic acid; zinc; In tetrahydrofuran; dichloromethane; acetone; 1.1: Claisen rearrangement;
DOI:10.1021/jo049358u