(2E,4E,6E,8E)-3,7-dimethyl-9-{6,6-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-1-cyclohexenyl}-2,4,6,8-nonatetraenoicacid ethyl ester

Base Information Edit

Chemical Name:(2E,4E,6E,8E)-3,7-dimethyl-9-{6,6-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-1-cyclohexenyl}-2,4,6,8-nonatetraenoicacid ethyl ester
CAS No.:1620084-74-3
Molecular Formula:C₂₇H₄₁BO₄
Molecular Weight:440.431
Hs Code.:
Mol file:1620084-74-3.mol

Synonyms:(2E,4E,6E,8E)-3,7-dimethyl-9-{6,6-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-1-cyclohexenyl}-2,4,6,8-nonatetraenoicacid ethyl ester

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Chemical Property of (2E,4E,6E,8E)-3,7-dimethyl-9-{6,6-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-1-cyclohexenyl}-2,4,6,8-nonatetraenoicacid ethyl ester Edit

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Technology Process of (2E,4E,6E,8E)-3,7-dimethyl-9-{6,6-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-1-cyclohexenyl}-2,4,6,8-nonatetraenoicacid ethyl ester

There total 8 articles about (2E,4E,6E,8E)-3,7-dimethyl-9-{6,6-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-1-cyclohexenyl}-2,4,6,8-nonatetraenoicacid ethyl ester 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: 36.0%

: 39760-56-0,3917-43-9,41891-54-7
triethyl 3-methyl-4-phosphonocrotonate

: 1620084-73-2
(2E,4E)-3-methyl-5-{6,6-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-1-cyclohexenyl}-2,4-pentadienal

: 1620084-74-3
(2E,4E,6E,8E)-3,7-dimethyl-9-{6,6-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-1-cyclohexenyl}-2,4,6,8-nonatetraenoicacid ethyl ester

Guidance literature:: triethyl 3-methyl-4-phosphonocrotonate; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.25h; Inert atmosphere;

(2E,4E)-3-methyl-5-{6,6-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-1-cyclohexenyl}-2,4-pentadienal; In tetrahydrofuran; mineral oil; at 20 ℃; for 20h; Inert atmosphere;
DOI:10.1016/j.bmcl.2014.05.041

Reference yield:

: 2979-10-4
ethyl 2,2-dimethyl-6-oxocyclohexane-1-carboxylate

: 1620084-74-3
(2E,4E,6E,8E)-3,7-dimethyl-9-{6,6-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-1-cyclohexenyl}-2,4,6,8-nonatetraenoicacid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium hydride / mineral oil; diethyl ether / 0.25 h / 0 °C / Inert atmosphere

1.2: 3 h / 0 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / diethyl ether; hexane / 2.5 h / 0 °C / Inert atmosphere

3.1: 4-methyl-morpholine; tetrapropylammonium perruthennate / dichloromethane / 2 h / 0 - 20 °C / Molecular sieve; Inert atmosphere

4.1: n-butyllithium / hexane; tetrahydrofuran / 0.75 h / -78 °C

4.2: 3 h

5.1: diisobutylaluminium hydride / diethyl ether; hexane / 2.5 h / 0 °C / Inert atmosphere

6.1: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; potassium phenolate / toluene / 16 h / 40 °C / Inert atmosphere

7.1: 4-methyl-morpholine; tetrapropylammonium perruthennate / dichloromethane / 1 h / 0 - 20 °C / Molecular sieve; Inert atmosphere

8.1: sodium hydride / mineral oil; tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

8.2: 20 h / 20 °C / Inert atmosphere

With 4-methyl-morpholine; bis-triphenylphosphine-palladium(II) chloride; n-butyllithium; tetrapropylammonium perruthennate; potassium phenolate; sodium hydride; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; mineral oil; 6.1: |Miyaura Borylation Reaction;
DOI:10.1016/j.bmcl.2014.05.041

Reference yield:

: 1257045-68-3
ethyl {6,6-dimethyl-2-(trifluoromethanesulfonyloxy)cyclohexene-1-yl}carboxylate

: 1620084-74-3
(2E,4E,6E,8E)-3,7-dimethyl-9-{6,6-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolanyl)-1-cyclohexenyl}-2,4,6,8-nonatetraenoicacid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: diisobutylaluminium hydride / diethyl ether; hexane / 2.5 h / 0 °C / Inert atmosphere

2.1: 4-methyl-morpholine; tetrapropylammonium perruthennate / dichloromethane / 2 h / 0 - 20 °C / Molecular sieve; Inert atmosphere

3.1: n-butyllithium / hexane; tetrahydrofuran / 0.75 h / -78 °C

3.2: 3 h

4.1: diisobutylaluminium hydride / diethyl ether; hexane / 2.5 h / 0 °C / Inert atmosphere

5.1: bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; potassium phenolate / toluene / 16 h / 40 °C / Inert atmosphere

6.1: 4-methyl-morpholine; tetrapropylammonium perruthennate / dichloromethane / 1 h / 0 - 20 °C / Molecular sieve; Inert atmosphere

7.1: sodium hydride / mineral oil; tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

7.2: 20 h / 20 °C / Inert atmosphere

With 4-methyl-morpholine; bis-triphenylphosphine-palladium(II) chloride; n-butyllithium; tetrapropylammonium perruthennate; potassium phenolate; sodium hydride; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; mineral oil; 5.1: |Miyaura Borylation Reaction;
DOI:10.1016/j.bmcl.2014.05.041