(4E,8E)-11-Benzenesulfonyl-2,5,9-trimethyl-2-(4-methyl-3-methylene-pentyl)-cycloundeca-4,8-dienone

Base Information

Chemical Name:(4E,8E)-11-Benzenesulfonyl-2,5,9-trimethyl-2-(4-methyl-3-methylene-pentyl)-cycloundeca-4,8-dienone
CAS No.:445389-08-2
Molecular Formula:C₂₇H₃₈O₃S
Molecular Weight:442.663
Hs Code.:

Synonyms:(4E,8E)-11-Benzenesulfonyl-2,5,9-trimethyl-2-(4-methyl-3-methylene-pentyl)-cycloundeca-4,8-dienone

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Chemical Property of (4E,8E)-11-Benzenesulfonyl-2,5,9-trimethyl-2-(4-methyl-3-methylene-pentyl)-cycloundeca-4,8-dienone

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Technology Process of (4E,8E)-11-Benzenesulfonyl-2,5,9-trimethyl-2-(4-methyl-3-methylene-pentyl)-cycloundeca-4,8-dienone

There total 5 articles about (4E,8E)-11-Benzenesulfonyl-2,5,9-trimethyl-2-(4-methyl-3-methylene-pentyl)-cycloundeca-4,8-dienone 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: 86.0%

: 445389-07-1
Carbonic acid (2E,6E)-9-(2-benzenesulfonyl-acetyl)-2,6,9,13-tetramethyl-12-methylene-tetradeca-2,6-dienyl ester methyl ester

: 445389-08-2
(4E,8E)-11-Benzenesulfonyl-2,5,9-trimethyl-2-(4-methyl-3-methylene-pentyl)-cycloundeca-4,8-dienone

Guidance literature:: Carbonic acid (2E,6E)-9-(2-benzenesulfonyl-acetyl)-2,6,9,13-tetramethyl-12-methylene-tetradeca-2,6-dienyl ester methyl ester; With potassium acetate; N,O-bis-(trimethylsilyl)-acetamide; In tetrahydrofuran; for 0.5h; Heating;

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,4-di(diphenylphosphino)-butane; In tetrahydrofuran; at 70 ℃; for 1h; Further stages.;
DOI:10.1021/ol026205p

Reference yield:

: tert-butyl-(5-isopropyl-1,2-dimethyl-hexa-1,5-dienyloxy)-dimethyl-silane

: 445389-08-2
(4E,8E)-11-Benzenesulfonyl-2,5,9-trimethyl-2-(4-methyl-3-methylene-pentyl)-cycloundeca-4,8-dienone

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / (Me₂N)3S⁽¹⁺⁾Me₃SiF₂^(1-) / tetrahydrofuran; dimethylformamide / 2.5 h / -30 - 0 °C

2.1: iPr₂NEt / CH₂Cl₂ / 1.5 h / 0 °C

3.1: 92 percent / NBS; NaHCO₃ / tetrahydrofuran / 2 h / -78 °C

4.1: 85 percent / dimethylformamide / 18 h / 23 °C

5.1: O,N-bis(trimethylsilyl)acetamide; KOAc / tetrahydrofuran / 0.5 h / Heating

5.2: 86 percent / Pd(Ph₃)4; 1,4-bis(diphenylphosphino)butane / tetrahydrofuran / 1 h / 70 °C

With N-Bromosuccinimide; tris(dimethylamino)sulfonium trimethylsilyldifluoride; potassium acetate; sodium hydrogencarbonate; N,O-bis-(trimethylsilyl)-acetamide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol026205p

Reference yield:

: 445389-04-8
Carbonic acid (2E,6E)-9-acetyl-2,6,9,13-tetramethyl-12-methylene-tetradeca-2,6-dienyl ester methyl ester

: 445389-08-2
(4E,8E)-11-Benzenesulfonyl-2,5,9-trimethyl-2-(4-methyl-3-methylene-pentyl)-cycloundeca-4,8-dienone

Guidance literature:: Multi-step reaction with 4 steps

1.1: iPr₂NEt / CH₂Cl₂ / 1.5 h / 0 °C

2.1: 92 percent / NBS; NaHCO₃ / tetrahydrofuran / 2 h / -78 °C

3.1: 85 percent / dimethylformamide / 18 h / 23 °C

4.1: O,N-bis(trimethylsilyl)acetamide; KOAc / tetrahydrofuran / 0.5 h / Heating

4.2: 86 percent / Pd(Ph₃)4; 1,4-bis(diphenylphosphino)butane / tetrahydrofuran / 1 h / 70 °C

With N-Bromosuccinimide; potassium acetate; sodium hydrogencarbonate; N,O-bis-(trimethylsilyl)-acetamide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol026205p