(1S,2S,4aS,8S,8aS,10aS)-2-(benzyloxy)-1,4a,8-trimethyl-6,9-dioxo-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-8a-carbonitrile

Base Information

Chemical Name:(1S,2S,4aS,8S,8aS,10aS)-2-(benzyloxy)-1,4a,8-trimethyl-6,9-dioxo-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-8a-carbonitrile
CAS No.:1207384-27-7
Molecular Formula:C₂₅H₂₉NO₃
Molecular Weight:391.51
Hs Code.:

Synonyms:(1S,2S,4aS,8S,8aS,10aS)-2-(benzyloxy)-1,4a,8-trimethyl-6,9-dioxo-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-8a-carbonitrile

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Chemical Property of (1S,2S,4aS,8S,8aS,10aS)-2-(benzyloxy)-1,4a,8-trimethyl-6,9-dioxo-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-8a-carbonitrile

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Technology Process of (1S,2S,4aS,8S,8aS,10aS)-2-(benzyloxy)-1,4a,8-trimethyl-6,9-dioxo-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-8a-carbonitrile

There total 11 articles about (1S,2S,4aS,8S,8aS,10aS)-2-(benzyloxy)-1,4a,8-trimethyl-6,9-dioxo-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-8a-carbonitrile 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: 60.0%

: C₁₁H₁₂O₂S

: 1207384-25-5
(4aS,5S,6S,8aS)-6-(benzyloxy)-5,8a-dimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydronaphthalene-2-carbonitrile

: 1207384-27-7
(1S,2S,4aS,8S,8aS,10aS)-2-(benzyloxy)-1,4a,8-trimethyl-6,9-dioxo-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-8a-carbonitrile

Guidance literature:: With caesium carbonate; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1021/ol902711b

Reference yield:

: C₂₀H₂₅NO₂

: 1207384-27-7
(1S,2S,4aS,8S,8aS,10aS)-2-(benzyloxy)-1,4a,8-trimethyl-6,9-dioxo-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-8a-carbonitrile

Guidance literature:: Multi-step reaction with 2 steps

1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.25 h / Inert atmosphere; Reflux

2: caesium carbonate / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

With caesium carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; benzene;
DOI:10.1021/jo501122k

Reference yield:

: 547-26-2
(+)-7-epi-α-cyperone

: 1207384-27-7
(1S,2S,4aS,8S,8aS,10aS)-2-(benzyloxy)-1,4a,8-trimethyl-6,9-dioxo-1,2,3,4,4a,6,7,8,8a,9,10,10a-dodecahydrophenanthrene-8a-carbonitrile

Guidance literature:: Multi-step reaction with 11 steps

1.1: tert-butyl alcohol; lithium; ammonia / hexane; tetrahydrofuran / 2 h / -33 °C / Inert atmosphere

2.1: sodium hydride; tetra-(n-butyl)ammonium iodide / tetrahydrofuran / 0 °C / Reflux; Inert atmosphere

3.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 20 °C / Inert atmosphere

4.1: sodium periodate / water; ethanol / 1 h / 20 °C / Inert atmosphere

5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 32 h / 20 °C / Inert atmosphere

6.1: potassium carbonate / methanol / 20 °C / Inert atmosphere

7.1: dipyridinium dichromate / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

8.1: sodium hydride / diethyl ether / 5 h / 20 °C / Inert atmosphere

9.1: hydroxylamine hydrochloride / water; ethanol / 1.5 h / Inert atmosphere; Reflux

9.2: 1 h / 20 °C / Inert atmosphere

10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.25 h / Inert atmosphere; Reflux

11.1: caesium carbonate / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

With sodium periodate; osmium(VIII) oxide; dipyridinium dichromate; hydroxylamine hydrochloride; ammonia; tetra-(n-butyl)ammonium iodide; lithium; sodium hydride; potassium carbonate; caesium carbonate; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tert-butyl alcohol; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; benzene; 1.1: |Birch Reduction / 5.1: |Baeyer-Villiger Ketone Oxidation;
DOI:10.1021/jo501122k