3-Isocyano-3,7,11,15-tetramethyl-1,6,10,14-hexadecatetraene

Base Information

• Chemical Name: 3-Isocyano-3,7,11,15-tetramethyl-1,6,10,14-hexadecatetraene
• CAS No.: 55784-75-3
• Molecular Formula: C21H33N
• Molecular Weight: 299.4934
• Nikkaji Number: J2.783.150H,J2.184.144G
• Metabolomics Workbench ID: 167010

Synonyms:3-Isocyano-3,7,11,15-tetramethyl-1,6,10,14-hexadecatetraene;1,6,10,14-Hexadecatetraene, 3-isocyano-3,7,11,15-tetramethyl-;55784-75-3;C21H33N;C21-H33-N;1,5,9,13-Tetramethyl-1-vinyl-4,8,12-tetradecatrienyl isocyanide;(6E,10E)-3-Isocyano-3,7,11,15-tetramethyl-1,6,10,14-hexadecatetrene

Chemical Property of 3-Isocyano-3,7,11,15-tetramethyl-1,6,10,14-hexadecatetraene

Chemical Property:

• XLogP3: 7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 10
• Exact Mass: 299.261300057
• Heavy Atom Count: 22
• Complexity: 477

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=CCCC(C)(C=C)[N+]#[C-])C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/CCC(C)(C=C)[N+]#[C-])/C)/C)C

Technology Process of 3-Isocyano-3,7,11,15-tetramethyl-1,6,10,14-hexadecatetraene

There total 21 articles about 3-Isocyano-3,7,11,15-tetramethyl-1,6,10,14-hexadecatetraene 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: 95.0%

N-((S,6E,10E)-3,7,11,15-tetramethylhexadeca-1,6,10,14-tetraen-3-yl)formamide (1295581-20-2) → (3S)-geranyllinaloisocyanide (57766-63-9,55784-75-3)

Guidance literature:

With carbon tetrabromide; triethylamine; triphenylphosphine; In dichloromethane; at -10 - 20 ℃; for 0.25h; Inert atmosphere;

DOI:10.1021/ol200308m

Reference yield: 92.0%

3-formamido-3,7,11,15-tetramethylhexadeca-1,6,10,14-tetraene (57766-64-0) → 3-isocyano-3,7,11,15-tetramethylhexadeca-1,6,10,14-tetraene (57766-63-9,154614-35-4,55784-75-3)

Guidance literature:

With carbon tetrabromide; triethylamine; triphenylphosphine; In dichloromethane; at -10 ℃; for 0.333333h; Inert atmosphere;

DOI:10.1021/ol200308m

Reference yield:

(S,E)-tert-butyl 4-(3-ethoxy-3-oxoprop-1-enyl)-2,2,4-trimethyloxazolidine-3-carboxylate (1295581-02-0) → (3S)-geranyllinaloisocyanide (57766-63-9,55784-75-3)

Guidance literature:

Multi-step reaction with 14 steps

1.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.58 h / -78 °C / Inert atmosphere

3.1: dichloromethane / 84 h / 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.58 h / -78 °C / Inert atmosphere

5.1: triethylamine / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

6.1: lithium bromide / tetrahydrofuran / 1 h / -10 °C / Inert atmosphere

7.1: n-butyllithium / tetrahydrofuran; hexane / 0.33 h / -78 - -10 °C / Inert atmosphere

7.2: 0.33 h / -10 - 20 °C / Inert atmosphere

8.1: dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); lithium triethylborohydride / tetrahydrofuran / 7.5 h / 0 °C / Inert atmosphere

9.1: water; scandium tris(trifluoromethanesulfonate) / acetonitrile / 74 h / 20 °C

10.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 9 h / 20 °C / Inert atmosphere

11.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / 0 - 20 °C / Inert atmosphere

12.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran; toluene / 0.17 h / 20 °C / Inert atmosphere

13.1: sodium hydrogencarbonate / dichloromethane; water / 4 h / 20 °C

14.1: carbon tetrabromide; triethylamine; triphenylphosphine / dichloromethane / 0.25 h / -10 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; n-butyllithium; dichloro [1,1'-bis(diphenylphosphino)propane]palladium(II); carbon tetrabromide; trimethylsilyl trifluoromethanesulfonate; palladium 10% on activated carbon; water; hydrogen; potassium hexamethylsilazane; diisobutylaluminium hydride; lithium triethylborohydride; sodium hydrogencarbonate; triethylamine; triphenylphosphine; lithium bromide; scandium tris(trifluoromethanesulfonate); 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; toluene; acetonitrile; 3.1: Wittig reaction / 11.1: Wittig reaction;

DOI:10.1021/ol200308m

upstream raw materials:

3-formamido-3,7,11,15-tetramethylhexadeca-1,6,10,14-tetraene

3-acetamido-3,7,11,15-tetramethylhexadeca-1,6,10,14-tetraene

(S,E)-tert-butyl 4-(3-ethoxy-3-oxoprop-1-enyl)-2,2,4-trimethyloxazolidine-3-carboxylate

(S)-tert-butyl 4-(3-ethoxy-3-oxopropyl)-2,2,4-trimethyloxazolidine-3-carboxylate

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