(2E,4E)-5-(3-Dimethylamino-2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienenitrile

Base Information

• Chemical Name: (2E,4E)-5-(3-Dimethylamino-2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienenitrile
• CAS No.: 99213-78-2
• Molecular Formula: C₁₇H₂₆N₂
• Molecular Weight: 258.407

Synonyms:(2E,4E)-5-(3-Dimethylamino-2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienenitrile

Chemical Property of (2E,4E)-5-(3-Dimethylamino-2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienenitrile

Chemical Property:

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Technology Process of (2E,4E)-5-(3-Dimethylamino-2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienenitrile

There total 3 articles about (2E,4E)-5-(3-Dimethylamino-2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienenitrile 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: 40.0%

diethyl 1-cyanomethylphosphonate (2537-48-6) + 4-(dimethylamino)-β-ionone (86948-67-6) → (2Z,4E)-5-(3-Dimethylamino-2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienenitrile + (2E,4E)-5-(3-Dimethylamino-2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienenitrile (99213-78-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 25 ℃; for 1h;

DOI:10.1021/ja00311a050

Reference yield:

4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one (79-77-6,14901-07-6) → (2E,4E)-5-(3-Dimethylamino-2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienenitrile (99213-78-2)

Guidance literature:

Multi-step reaction with 3 steps

1: N-bromosuccinimide / CCl₄; hexane / 1 h / Heating

2: 68 percent / sodium carbonate / tetrahydrofuran; H₂O / 5 h / Ambient temperature

3: 40 percent / NaH / tetrahydrofuran / 1 h / 25 °C

With N-Bromosuccinimide; sodium hydride; sodium carbonate; In tetrahydrofuran; tetrachloromethane; hexane; water;

DOI:10.1021/ja00311a050

Reference yield:

trans-4-bromo-β-ionone (84817-80-1) → (2E,4E)-5-(3-Dimethylamino-2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienenitrile (99213-78-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / sodium carbonate / tetrahydrofuran; H₂O / 5 h / Ambient temperature

2: 40 percent / NaH / tetrahydrofuran / 1 h / 25 °C

With sodium hydride; sodium carbonate; In tetrahydrofuran; water;

DOI:10.1021/ja00311a050

upstream raw materials:

diethyl 1-cyanomethylphosphonate

4-(dimethylamino)-β-ionone

4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

trans-4-bromo-β-ionone

Downstream raw materials:

(2E,4E)-5-(3-Dimethylamino-2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-penta-2,4-dienal

(2E,4E,6E,8E)-9-(3-Dimethylamino-2,6,6-trimethyl-cyclohex-1-enyl)-3,7-dimethyl-nona-2,4,6,8-tetraenal

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