(8,18-¹³C₂)-(2E,4E)-3-methyl-5-(2,2,6-trimethylcyclohexen-1-yl)ethenyl-2,4-pentadienol

Base Information

• Chemical Name: (8,18-¹³C₂)-(2E,4E)-3-methyl-5-(2,2,6-trimethylcyclohexen-1-yl)ethenyl-2,4-pentadienol
• CAS No.: 864363-18-8
• Molecular Formula: C₁₅H₂₄O
• Molecular Weight: 222.333

Synonyms:(8,18-¹³C₂)-(2E,4E)-3-methyl-5-(2,2,6-trimethylcyclohexen-1-yl)ethenyl-2,4-pentadienol

Chemical Property of (8,18-¹³C₂)-(2E,4E)-3-methyl-5-(2,2,6-trimethylcyclohexen-1-yl)ethenyl-2,4-pentadienol

Chemical Property:

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Technology Process of (8,18-¹³C₂)-(2E,4E)-3-methyl-5-(2,2,6-trimethylcyclohexen-1-yl)ethenyl-2,4-pentadienol

There total 7 articles about (8,18-¹³C₂)-(2E,4E)-3-methyl-5-(2,2,6-trimethylcyclohexen-1-yl)ethenyl-2,4-pentadienol 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: 67.0%

(8,18-13C2)-(E)-2-(2,2,6-trimethylcyclohexen-1-yl)ethenyl nonafluorobutanesulfonate (864363-17-7) + (2E)-3-methyl-3-tributylstannylprop-2-en-1-ol (121882-41-5,124607-17-6,850354-34-6) → (8,18-13C2)-(2E,4E)-3-methyl-5-(2,2,6-trimethylcyclohexen-1-yl)ethenyl-2,4-pentadienol (864363-18-8)

Guidance literature:

With triphenyl-arsane; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1055/s-2005-865294

Reference yield:

(18-13C)-2,2,6-trimethylcyclohexanone (864363-14-4) → (8,18-13C2)-(2E,4E)-3-methyl-5-(2,2,6-trimethylcyclohexen-1-yl)ethenyl-2,4-pentadienol (864363-18-8)

Guidance literature:

Multi-step reaction with 6 steps

1.1: LDA / tetrahydrofuran; hexane / 0.5 h / -70 °C

1.2: 79 percent / tetrahydrofuran; hexane / 2 h / -70 °C

2.1: 93 percent / thionyl chloride; pyridine / 0.17 h / 9 °C

3.1: LiAlH₄ / diethyl ether / 0.5 h / 0 °C

4.1: diisopropylmagnesium bromide / tetrahydrofuran / 0.17 h / 0 °C

4.2: 870 mg / azodicarbonyldipiperidine / tetrahydrofuran / 2 h / 0 °C

5.1: 63 percent / t-BuOK / tetrahydrofuran / 1 h / Heating

6.1: 67 percent / AsPh₃ / Pd₂dba3*CHCl₃ / dimethylformamide / 2 h / 20 °C

With pyridine; lithium aluminium tetrahydride; thionyl chloride; triphenyl-arsane; diisopropylmagnesium bromide; potassium tert-butylate; lithium diisopropyl amide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; diethyl ether; hexane; N,N-dimethyl-formamide; 6.1: Stille coupling reaction;

DOI:10.1055/s-2005-865294

Reference yield:

(8,18-13C2) ethyl (2,2,6-trimethylcyclohexen-1-yl)acetaldehyde (864363-16-6) → (8,18-13C2)-(2E,4E)-3-methyl-5-(2,2,6-trimethylcyclohexen-1-yl)ethenyl-2,4-pentadienol (864363-18-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / t-BuOK / tetrahydrofuran / 1 h / Heating

2: 67 percent / AsPh₃ / Pd₂dba3*CHCl₃ / dimethylformamide / 2 h / 20 °C

With triphenyl-arsane; potassium tert-butylate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; N,N-dimethyl-formamide; 2: Stille coupling reaction;

DOI:10.1055/s-2005-865294

upstream raw materials:

(8,18-¹³C₂)-(E)-2-(2,2,6-trimethylcyclohexen-1-yl)ethenyl nonafluorobutanesulfonate

(2E)-3-methyl-3-tributylstannylprop-2-en-1-ol

(18-¹³C)-2,2,6-trimethylcyclohexanone

(8,18-¹³C₂) ethyl (2,2,6-trimethylcyclohexen-1-yl)acetaldehyde

Downstream raw materials:

(8,18-¹³C₂)-(2E,4E)-3-methyl-5-(2,2,6-trimethylcyclohexen-1-yl)ethenyl-2,4-pentadienal

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