(1S,4R,4aS,8S,8aR)-8-Hydroxy-8-((R)-toluene-4-sulfinylmethyl)-4,4a,8,8a-tetrahydro-1H-1,4-methano-naphthalen-5-one

Base Information

Chemical Name:(1S,4R,4aS,8S,8aR)-8-Hydroxy-8-((R)-toluene-4-sulfinylmethyl)-4,4a,8,8a-tetrahydro-1H-1,4-methano-naphthalen-5-one
CAS No.:170211-98-0
Molecular Formula:C₁₉H₂₀O₃S
Molecular Weight:328.432
Hs Code.:

Synonyms:(1S,4R,4aS,8S,8aR)-8-Hydroxy-8-((R)-toluene-4-sulfinylmethyl)-4,4a,8,8a-tetrahydro-1H-1,4-methano-naphthalen-5-one

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Chemical Property of (1S,4R,4aS,8S,8aR)-8-Hydroxy-8-((R)-toluene-4-sulfinylmethyl)-4,4a,8,8a-tetrahydro-1H-1,4-methano-naphthalen-5-one

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Technology Process of (1S,4R,4aS,8S,8aR)-8-Hydroxy-8-((R)-toluene-4-sulfinylmethyl)-4,4a,8,8a-tetrahydro-1H-1,4-methano-naphthalen-5-one

There total 3 articles about (1S,4R,4aS,8S,8aR)-8-Hydroxy-8-((R)-toluene-4-sulfinylmethyl)-4,4a,8,8a-tetrahydro-1H-1,4-methano-naphthalen-5-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:

: 542-92-7,25568-84-7,7313-32-8
cyclopenta-1,3-diene

: 170117-33-6
[(S)R]-4-hydroxy-4-[p-(tolylsulfinyl)methyl]cyclohexa-2,5-dienone

: 170117-34-7
(1R,4S,4aR,8R,8aS)-8-Hydroxy-8-((R)-toluene-4-sulfinylmethyl)-4,4a,8,8a-tetrahydro-1H-1,4-methano-naphthalen-5-one

: 170211-98-0
(1S,4R,4aS,8S,8aR)-8-Hydroxy-8-((R)-toluene-4-sulfinylmethyl)-4,4a,8,8a-tetrahydro-1H-1,4-methano-naphthalen-5-one

Guidance literature:: In dichloromethane; at 25 ℃; for 168h; Yield given. Yields of byproduct given;
DOI:10.1021/jo9712308

Reference yield:

: 1519-39-7
(R)-methyl p-tolyl sulfoxide

: 170211-98-0
(1S,4R,4aS,8S,8aR)-8-Hydroxy-8-((R)-toluene-4-sulfinylmethyl)-4,4a,8,8a-tetrahydro-1H-1,4-methano-naphthalen-5-one

Guidance literature:: Multi-step reaction with 3 steps

1: BuLi, diisopropylamine / hexane; tetrahydrofuran / 2 h / -78 °C

2: 5percent oxalic acid / tetrahydrofuran; H₂O

3: BF₃*Et₂O / CH₂Cl₂ / 1 h / -96 °C

With n-butyllithium; boron trifluoride diethyl etherate; oxalic acid; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; water;
DOI:10.1021/jo9712308

Reference yield:

: 170117-32-5
[(S)R]-4-hydroxy-4-[(p-tolylsulfinyl)methyl]-2,5-cyclohexadienone dimethyl acetal

: 170211-98-0
(1S,4R,4aS,8S,8aR)-8-Hydroxy-8-((R)-toluene-4-sulfinylmethyl)-4,4a,8,8a-tetrahydro-1H-1,4-methano-naphthalen-5-one

Guidance literature:: Multi-step reaction with 2 steps

1: 5percent oxalic acid / tetrahydrofuran; H₂O

2: BF₃*Et₂O / CH₂Cl₂ / 1 h / -96 °C

With boron trifluoride diethyl etherate; oxalic acid; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/jo9712308