[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

Base Information

• Chemical Name: [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
• CAS No.: 1342310-23-9
• Molecular Formula: C₂₆H₄₂OSi
• Molecular Weight: 400.682
• Mol file: 1342310-23-9.mol

Synonyms:

Chemical Property of [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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [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

There total 4 articles about [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 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:

tert-butyl((3-iodobut-2-en-1-yl)oxy)dimethylsilane + [10,11-13C2]-1,3,3-trimethyl-2-((1E,3E)-3-methylhexa-1,3-dien-5-ynyl)cyclohex-1-ene (1342310-22-8) → [10,11-13C2]-((2Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,6,8-trien-4-ynyloxy)(tert-butyl)dimethylsilane + [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 (1342310-23-9)

Guidance literature:

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; isopropylamine; for 3.5h; optical yield given as %de;

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]-((2Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,6,8-trien-4-ynyloxy)(tert-butyl)dimethylsilane + [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 (1342310-23-9)

Guidance literature:

Multi-step reaction with 4 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

4.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; isopropylamine / 3.5 h

With copper(l) iodide; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; isopropylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; 4.1: Sonogashira reaction;

DOI:10.1016/j.tet.2011.07.092

Reference yield:

[10,11-13C2]-(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-enyl)penta-2,4-dienal (100187-26-6) → [10,11-13C2]-((2Z,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,6,8-trien-4-ynyloxy)(tert-butyl)dimethylsilane + [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 (1342310-23-9)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: -78 - 20 °C

2.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; isopropylamine / 3.5 h

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; isopropylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; 2.1: Sonogashira reaction;

DOI:10.1016/j.tet.2011.07.092

upstream raw materials:

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

[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

Refernces