[10,11-13C₂]-1,3,3-trimethyl-2-((1E,3E)-3-methylhexa-1,3-dien-5-ynyl)cyclohex-1-ene

Base Information

• Chemical Name: [10,11-13C₂]-1,3,3-trimethyl-2-((1E,3E)-3-methylhexa-1,3-dien-5-ynyl)cyclohex-1-ene
• CAS No.: 1342310-22-8
• Molecular Formula: C₁₆H₂₂
• Molecular Weight: 216.329

Synonyms:[10,11-13C₂]-1,3,3-trimethyl-2-((1E,3E)-3-methylhexa-1,3-dien-5-ynyl)cyclohex-1-ene

Chemical Property of [10,11-13C₂]-1,3,3-trimethyl-2-((1E,3E)-3-methylhexa-1,3-dien-5-ynyl)cyclohex-1-ene

Chemical Property:

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Technology Process of [10,11-13C₂]-1,3,3-trimethyl-2-((1E,3E)-3-methylhexa-1,3-dien-5-ynyl)cyclohex-1-ene

There total 3 articles about [10,11-13C₂]-1,3,3-trimethyl-2-((1E,3E)-3-methylhexa-1,3-dien-5-ynyl)cyclohex-1-ene 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: 42.0%

[10,11-13C2]-(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienal (100187-26-6) + diazomethyl-trimethyl-silane (18107-18-1) → [10,11-13C2]-1,3,3-trimethyl-2-((1E,3E)-3-methylhexa-1,3-dien-5-ynyl)cyclohex-1-ene (1342310-22-8)

Guidance literature:

diazomethyl-trimethyl-silane; With lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.75h;

[10,11-13C₂]-(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienal; In tetrahydrofuran; diethyl ether; at -78 - 20 ℃;

DOI:10.1016/j.tet.2011.07.092

Reference yield:

[10,11-13C2]-(4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate (122040-78-2) → [10,11-13C2]-1,3,3-trimethyl-2-((1E,3E)-3-methylhexa-1,3-dien-5-ynyl)cyclohex-1-ene (1342310-22-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium aluminium tetrahydride / diethyl ether / -78 - 20 °C

2.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / 20 °C / Molecular sieve

3.1: lithium diisopropyl amide / tetrahydrofuran; diethyl ether / 0.75 h / -78 °C

3.2: -78 - 20 °C

With lithium aluminium tetrahydride; tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/j.tet.2011.07.092

Reference yield:

C13(13)C2H24O → [10,11-13C2]-1,3,3-trimethyl-2-((1E,3E)-3-methylhexa-1,3-dien-5-ynyl)cyclohex-1-ene (1342310-22-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / 20 °C / Molecular sieve

2.1: lithium diisopropyl amide / tetrahydrofuran; diethyl ether / 0.75 h / -78 °C

2.2: -78 - 20 °C

With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/j.tet.2011.07.092

upstream raw materials:

[10,11-13C₂]-(4E)-ethyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienoate

[10,11-13C₂]-(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienal

diazomethyl-trimethyl-silane

Downstream raw materials:

[10,11-13C₂]-((2E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,6,8-trien-4-ynyloxy)(tert-butyl)dimethylsilane

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