(3aR,8aS)-5-Benzenesulfinylmethyl-1-isopropyl-3a,8a-dimethyl-2,3,3a,4,6,7,8,8a,9,10-decahydro-benzo[f]azulene

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Chemical Name:(3aR,8aS)-5-Benzenesulfinylmethyl-1-isopropyl-3a,8a-dimethyl-2,3,3a,4,6,7,8,8a,9,10-decahydro-benzo[f]azulene
CAS No.:133728-55-9
Molecular Formula:C₂₆H₃₆OS
Molecular Weight:396.637
Hs Code.:

Synonyms:(3aR,8aS)-5-Benzenesulfinylmethyl-1-isopropyl-3a,8a-dimethyl-2,3,3a,4,6,7,8,8a,9,10-decahydro-benzo[f]azulene

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Chemical Property of (3aR,8aS)-5-Benzenesulfinylmethyl-1-isopropyl-3a,8a-dimethyl-2,3,3a,4,6,7,8,8a,9,10-decahydro-benzo[f]azulene

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Technology Process of (3aR,8aS)-5-Benzenesulfinylmethyl-1-isopropyl-3a,8a-dimethyl-2,3,3a,4,6,7,8,8a,9,10-decahydro-benzo[f]azulene

There total 16 articles about (3aR,8aS)-5-Benzenesulfinylmethyl-1-isopropyl-3a,8a-dimethyl-2,3,3a,4,6,7,8,8a,9,10-decahydro-benzo[f]azulene 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: 90.0%

: 4972-29-6
benzenesulphinyl chloride

: 133728-54-8
(3aR*,4aR*,8aS*)-2,3,3a,4,4a,5,6,7,8,8a,9,10-dodecahydro-3a,8a-dimethyl-1-isopropyl-5-methylenebenzazulene

: 133728-55-9
(3aR,8aS)-5-Benzenesulfinylmethyl-1-isopropyl-3a,8a-dimethyl-2,3,3a,4,6,7,8,8a,9,10-decahydro-benzo[f]azulene

Guidance literature:: With ethylaluminum dichloride; In diethyl ether; toluene; for 15h; Ambient temperature;
DOI:10.1021/jo00012a035

Reference yield:

: 57205-09-1
ethyl 6-oxocyclohex-1-enecarboxylate

: 133728-55-9
(3aR,8aS)-5-Benzenesulfinylmethyl-1-isopropyl-3a,8a-dimethyl-2,3,3a,4,6,7,8,8a,9,10-decahydro-benzo[f]azulene

Guidance literature:: Multi-step reaction with 15 steps

2: 1) NaH / 1) THF, -30 deg C, 10 min, 2) THF, -35 deg C, 4 h

3: 1) copper(I) iodide / 1) ether, -15 deg C, 10 min, 2) ether, -78 -> -25 deg C, 3 h

4: 90 percent / LiAlH₄ / diethyl ether / 0.75 h / 0 °C

5: 1) TEA, methanesulfonyl chloride, 2) LiCl / 1) THF, -25 deg C, 4 h, 2) THF, -25 deg C, 8 h

6: 1) LDA, HMPA / 1) hexane, THF, -78 deg C, 30 min., 2) THF, a) -78 deg C, 1 h, b) -55 deg C, 20 h

7: 2) 10percent aq. HCl / 1) THF, room temp., 34 h, 2) THF, room temp., 45 min

8: 94 percent / EtAlCl₂ / toluene / 1.5 h / 0 °C

9: 88 percent / AlCl₃, LiAlH₄ / diethyl ether / 0.5 h / Heating

10: 1) B₂H₆, 2) 3N NaOH, 30percent aq. H₂O₂, K₂CO₃ / 1) THF, a) 1 h, 0 deg C, b) 30 min., room temp., 2) H₂O, 45 min., room temp.

11: 95 percent / PCC / CH₂Cl₂ / 3 h / Ambient temperature

12: NaOCH₃ / methanol / 16 h / Ambient temperature

13: tetrahydrofuran / 0.5 h / -78 °C

14: 88 percent / 50percent aq. HF / tetrahydrofuran / 1 h / Ambient temperature

15: 90 percent / EtAlCl₂ / toluene; diethyl ether / 15 h / Ambient temperature

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; aluminium trichloride; TEA; hydrogen fluoride; dihydrogen peroxide; sodium methylate; ethylaluminum dichloride; sodium hydride; potassium carbonate; methanesulfonyl chloride; pyridinium chlorochromate; lithium chloride; diborane; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
DOI:10.1021/jo00012a035

Reference yield:

: 130216-29-4
1-(chloromethyl)-6-(dimethylphenylsilyl)-2-methyl-1-cyclohexene

: 133728-55-9
(3aR,8aS)-5-Benzenesulfinylmethyl-1-isopropyl-3a,8a-dimethyl-2,3,3a,4,6,7,8,8a,9,10-decahydro-benzo[f]azulene

Guidance literature:: Multi-step reaction with 10 steps

1: 1) LDA, HMPA / 1) hexane, THF, -78 deg C, 30 min., 2) THF, a) -78 deg C, 1 h, b) -55 deg C, 20 h

2: 2) 10percent aq. HCl / 1) THF, room temp., 34 h, 2) THF, room temp., 45 min

3: 94 percent / EtAlCl₂ / toluene / 1.5 h / 0 °C

4: 88 percent / AlCl₃, LiAlH₄ / diethyl ether / 0.5 h / Heating

5: 1) B₂H₆, 2) 3N NaOH, 30percent aq. H₂O₂, K₂CO₃ / 1) THF, a) 1 h, 0 deg C, b) 30 min., room temp., 2) H₂O, 45 min., room temp.

6: 95 percent / PCC / CH₂Cl₂ / 3 h / Ambient temperature

7: NaOCH₃ / methanol / 16 h / Ambient temperature

8: tetrahydrofuran / 0.5 h / -78 °C

9: 88 percent / 50percent aq. HF / tetrahydrofuran / 1 h / Ambient temperature

10: 90 percent / EtAlCl₂ / toluene; diethyl ether / 15 h / Ambient temperature

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; lithium aluminium tetrahydride; aluminium trichloride; hydrogen fluoride; dihydrogen peroxide; sodium methylate; ethylaluminum dichloride; potassium carbonate; pyridinium chlorochromate; diborane; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
DOI:10.1021/jo00012a035