1-{2-[(1S,6S)-6-((E)-4,8-Dimethyl-nona-3,7-dienyl)-1,6-dimethyl-cyclohexa-2,4-dienyl]-ethylselanyl}-2-nitro-benzene

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Chemical Name:1-{2-[(1S,6S)-6-((E)-4,8-Dimethyl-nona-3,7-dienyl)-1,6-dimethyl-cyclohexa-2,4-dienyl]-ethylselanyl}-2-nitro-benzene
CAS No.:915315-75-2
Molecular Formula:C₂₇H₃₇NO₂Se
Molecular Weight:486.556
Hs Code.:

Synonyms:1-{2-[(1S,6S)-6-((E)-4,8-Dimethyl-nona-3,7-dienyl)-1,6-dimethyl-cyclohexa-2,4-dienyl]-ethylselanyl}-2-nitro-benzene

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Chemical Property of 1-{2-[(1S,6S)-6-((E)-4,8-Dimethyl-nona-3,7-dienyl)-1,6-dimethyl-cyclohexa-2,4-dienyl]-ethylselanyl}-2-nitro-benzene

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Technology Process of 1-{2-[(1S,6S)-6-((E)-4,8-Dimethyl-nona-3,7-dienyl)-1,6-dimethyl-cyclohexa-2,4-dienyl]-ethylselanyl}-2-nitro-benzene

There total 18 articles about 1-{2-[(1S,6S)-6-((E)-4,8-Dimethyl-nona-3,7-dienyl)-1,6-dimethyl-cyclohexa-2,4-dienyl]-ethylselanyl}-2-nitro-benzene 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:

: 915315-58-1
(4'aR,8'aS)-dimethyl-1',3',4',5',8',8'a-hexahydro-spiro[[1,3]dioxolane-2,2'-naphthalene]

: 915315-75-2
1-{2-[(1S,6S)-6-((E)-4,8-Dimethyl-nona-3,7-dienyl)-1,6-dimethyl-cyclohexa-2,4-dienyl]-ethylselanyl}-2-nitro-benzene

Guidance literature:: Multi-step reaction with 12 steps

1.1: ozone gas / CH₂Cl₂; methanol / 0.58 h / -78 °C

1.2: 15.0 g / sodium borohydride / CH₂Cl₂; methanol / 30 h / -15 °C

2.1: 31.0 g / 4-dimethylaminopyridine / dimethylformamide; various solvent(s) / 24 h / 20 °C

3.1: para-toluenesulfonic acid monohydrate / acetone; H₂O / 3 h / Heating

4.1: para-toluenesulfonic acid monohydrate / tetrahydrofuran / 1 h / Heating

5.1: lithium hydride / tetrahydrofuran; toluene / 65 h

5.2: N-bromosuccinimide; dibenzoylperoxide / CCl₄ / 0.75 h

5.3: 15.0 g / potassium tert-butoxide; tetrabutyltinhydride; 2,2'-azobisisobutyronitrile / tetrahydrofuran / 77 h / Heating

6.1: 6.40 g / MgSO₄; tetramethylammoniumhydroxide; tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C

7.1: 85 percent / PMe₃ / tetrahydrofuran / 1 h / 20 °C

8.1: 95 percent / aq. H₂O₂ / tetrahydrofuran / 0 °C

9.1: BH₃*Me₂S / tetrahydrofuran / 1.25 h / 0 - 20 °C

10.1: 80.5 percent / CH₂Cl₂; Ph₃As; Cs₂CO₃ / PdCl₂(dppf) / dimethylformamide; tetrahydrofuran; H₂O / 40 h / 20 °C

11.1: 92 percent / tetramethylammonium hydroxide; tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C

12.1: PMe₃ / tetrahydrofuran / 1 h / 20 °C

With dmap; dichloromethane; triphenyl-arsane; dimethylsulfide borane complex; tetramethyl ammoniumhydroxide; tetrabutyl ammonium fluoride; dihydrogen peroxide; lithium hydride; magnesium sulfate; caesium carbonate; toluene-4-sulfonic acid; ozone; trimethylphosphane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 10.1: Suzuki-Miyaura cross-coupling;
DOI:10.1021/ol061962z

Reference yield:

: 915315-57-0
(8'aS)-methyl-1',3',4',5',8',8'a-hexahydro-spiro[[1,3]dioxolane-2,2'-naphthalene]-(4'aS)-carbonitrile

: 915315-75-2
1-{2-[(1S,6S)-6-((E)-4,8-Dimethyl-nona-3,7-dienyl)-1,6-dimethyl-cyclohexa-2,4-dienyl]-ethylselanyl}-2-nitro-benzene

Guidance literature:: Multi-step reaction with 15 steps

1.1: diisobutylaluminum hydride / toluene / 2 h

2.1: hydrazine hydrate; hydrazine dihydrochloride / triethylene glycol / 1 h / 130 °C

3.1: 8.55 g / KOH / 220 °C

4.1: ozone gas / CH₂Cl₂; methanol / 0.58 h / -78 °C

4.2: 15.0 g / sodium borohydride / CH₂Cl₂; methanol / 30 h / -15 °C

5.1: 31.0 g / 4-dimethylaminopyridine / dimethylformamide; various solvent(s) / 24 h / 20 °C

6.1: para-toluenesulfonic acid monohydrate / acetone; H₂O / 3 h / Heating

7.1: para-toluenesulfonic acid monohydrate / tetrahydrofuran / 1 h / Heating

8.1: lithium hydride / tetrahydrofuran; toluene / 65 h

8.2: N-bromosuccinimide; dibenzoylperoxide / CCl₄ / 0.75 h

8.3: 15.0 g / potassium tert-butoxide; tetrabutyltinhydride; 2,2'-azobisisobutyronitrile / tetrahydrofuran / 77 h / Heating

9.1: 6.40 g / MgSO₄; tetramethylammoniumhydroxide; tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C

10.1: 85 percent / PMe₃ / tetrahydrofuran / 1 h / 20 °C

11.1: 95 percent / aq. H₂O₂ / tetrahydrofuran / 0 °C

12.1: BH₃*Me₂S / tetrahydrofuran / 1.25 h / 0 - 20 °C

13.1: 80.5 percent / CH₂Cl₂; Ph₃As; Cs₂CO₃ / PdCl₂(dppf) / dimethylformamide; tetrahydrofuran; H₂O / 40 h / 20 °C

14.1: 92 percent / tetramethylammonium hydroxide; tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C

15.1: PMe₃ / tetrahydrofuran / 1 h / 20 °C

With dmap; potassium hydroxide; hydrazine dihydrochloride; dichloromethane; triphenyl-arsane; dimethylsulfide borane complex; tetramethyl ammoniumhydroxide; tetrabutyl ammonium fluoride; dihydrogen peroxide; lithium hydride; diisobutylaluminium hydride; magnesium sulfate; caesium carbonate; toluene-4-sulfonic acid; ozone; hydrazine hydrate; trimethylphosphane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol; 13.1: Suzuki-Miyaura cross-coupling;
DOI:10.1021/ol061962z

Reference yield:

: C-((4'aS,8'aS)-8'a-Methyl-1',3',4',5',8',8'a-hexahydro-spiro[[1,3]dioxolane-2,2'-naphthalen]-4'a-yl)-methyleneamine

: 915315-75-2
1-{2-[(1S,6S)-6-((E)-4,8-Dimethyl-nona-3,7-dienyl)-1,6-dimethyl-cyclohexa-2,4-dienyl]-ethylselanyl}-2-nitro-benzene

Guidance literature:: Multi-step reaction with 14 steps

1.1: hydrazine hydrate; hydrazine dihydrochloride / triethylene glycol / 1 h / 130 °C

2.1: 8.55 g / KOH / 220 °C

3.1: ozone gas / CH₂Cl₂; methanol / 0.58 h / -78 °C

3.2: 15.0 g / sodium borohydride / CH₂Cl₂; methanol / 30 h / -15 °C

4.1: 31.0 g / 4-dimethylaminopyridine / dimethylformamide; various solvent(s) / 24 h / 20 °C

5.1: para-toluenesulfonic acid monohydrate / acetone; H₂O / 3 h / Heating

6.1: para-toluenesulfonic acid monohydrate / tetrahydrofuran / 1 h / Heating

7.1: lithium hydride / tetrahydrofuran; toluene / 65 h

7.2: N-bromosuccinimide; dibenzoylperoxide / CCl₄ / 0.75 h

7.3: 15.0 g / potassium tert-butoxide; tetrabutyltinhydride; 2,2'-azobisisobutyronitrile / tetrahydrofuran / 77 h / Heating

8.1: 6.40 g / MgSO₄; tetramethylammoniumhydroxide; tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h / 0 °C

9.1: 85 percent / PMe₃ / tetrahydrofuran / 1 h / 20 °C

10.1: 95 percent / aq. H₂O₂ / tetrahydrofuran / 0 °C

11.1: BH₃*Me₂S / tetrahydrofuran / 1.25 h / 0 - 20 °C

12.1: 80.5 percent / CH₂Cl₂; Ph₃As; Cs₂CO₃ / PdCl₂(dppf) / dimethylformamide; tetrahydrofuran; H₂O / 40 h / 20 °C

13.1: 92 percent / tetramethylammonium hydroxide; tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C

14.1: PMe₃ / tetrahydrofuran / 1 h / 20 °C

With dmap; potassium hydroxide; hydrazine dihydrochloride; dichloromethane; triphenyl-arsane; dimethylsulfide borane complex; tetramethyl ammoniumhydroxide; tetrabutyl ammonium fluoride; dihydrogen peroxide; lithium hydride; magnesium sulfate; caesium carbonate; toluene-4-sulfonic acid; ozone; hydrazine hydrate; trimethylphosphane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol; 12.1: Suzuki-Miyaura cross-coupling;
DOI:10.1021/ol061962z