9-(tert-butyl)-12-(4-methoxyphenyl)-8-oxaspiro[5.6]dodeca-9,11-dien-7-one

Base Information

Chemical Name:9-(tert-butyl)-12-(4-methoxyphenyl)-8-oxaspiro[5.6]dodeca-9,11-dien-7-one
CAS No.:1558755-42-2
Molecular Formula:C₂₂H₂₈O₃
Molecular Weight:340.463
Hs Code.:

Synonyms:

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Chemical Property of 9-(tert-butyl)-12-(4-methoxyphenyl)-8-oxaspiro[5.6]dodeca-9,11-dien-7-one

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Technology Process of 9-(tert-butyl)-12-(4-methoxyphenyl)-8-oxaspiro[5.6]dodeca-9,11-dien-7-one

There total 11 articles about 9-(tert-butyl)-12-(4-methoxyphenyl)-8-oxaspiro[5.6]dodeca-9,11-dien-7-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: 48.0%

: 40195-26-4
1-methoxy-1-trimethylsilyloxymethylenecyclohexane

: (3SR,4RS)-4-methoxy-1-(4-methoxyphenyl)-5,5-dimethylhex-1-yn-3-yl acetate

: methyl 1-[(3RS,4SR)-4-methoxy-1-(4-methoxyphenyl)-5,5-dimethylhex-1-yn-3-yl]cyclohexanecarboxylate

: 1558755-42-2
9-(tert-butyl)-12-(4-methoxyphenyl)-8-oxaspiro[5.6]dodeca-9,11-dien-7-one

Guidance literature:: With bismuth(lll) trifluoromethanesulfonate; In nitromethane; at 20 ℃; for 1h; diastereoselective reaction; Inert atmosphere; Schlenk technique;
DOI:10.1021/ja411772n

Reference yield:

: 75-97-8
3,3-dimethyl-butan-2-one

: methyl 1-[(3RS,4SR)-4-methoxy-1-(4-methoxyphenyl)-5,5-dimethylhex-1-yn-3-yl]cyclohexanecarboxylate

: 1558755-42-2
9-(tert-butyl)-12-(4-methoxyphenyl)-8-oxaspiro[5.6]dodeca-9,11-dien-7-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: sodium hydroxide; potassium permanganate / water / 16.5 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

1.2: Cooling; Inert atmosphere; Schlenk technique

2.1: sodium hydroxide; sodium tetrahydroborate / water / 16.5 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

2.2: Inert atmosphere; Schlenk technique

3.1: acetyl chloride / 4 h / 65 °C / Inert atmosphere; Schlenk technique

4.1: sodium hydride / mineral oil; tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere; Schlenk technique

4.2: 3 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

5.1: lithium aluminium tetrahydride / diethyl ether / 16 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere; Schlenk technique

6.2: 1 h / -78 - 20 °C / Inert atmosphere; Schlenk technique

7.1: n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 °C / Inert atmosphere; Schlenk technique

7.2: 2 h / -78 °C / Inert atmosphere; Schlenk technique

8.1: dmap; pyridine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

9.1: bismuth(lll) trifluoromethanesulfonate / nitromethane / 1 h / 20 °C / Inert atmosphere; Schlenk technique

With bismuth(lll) trifluoromethanesulfonate; pyridine; dmap; sodium tetrahydroborate; potassium permanganate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; acetyl chloride; sodium hydroxide; In tetrahydrofuran; diethyl ether; nitromethane; hexane; dichloromethane; water; mineral oil; 6.1: |Swern Oxidation / 6.2: |Swern Oxidation;
DOI:10.1021/ja411772n

Reference yield:

: (3SR,4RS)-4-methoxy-1-(4-methoxyphenyl)-5,5-dimethylhex-1-yn-3-ol

: methyl 1-[(3RS,4SR)-4-methoxy-1-(4-methoxyphenyl)-5,5-dimethylhex-1-yn-3-yl]cyclohexanecarboxylate

: 1558755-42-2
9-(tert-butyl)-12-(4-methoxyphenyl)-8-oxaspiro[5.6]dodeca-9,11-dien-7-one

Guidance literature:: Multi-step reaction with 2 steps

1: dmap; pyridine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere; Schlenk technique

2: bismuth(lll) trifluoromethanesulfonate / nitromethane / 1 h / 20 °C / Inert atmosphere; Schlenk technique

With bismuth(lll) trifluoromethanesulfonate; pyridine; dmap; In nitromethane; dichloromethane;
DOI:10.1021/ja411772n