(E)-2-dodecenyl phenyl sulphide

Base Information

• Chemical Name: (E)-2-dodecenyl phenyl sulphide
• CAS No.: 66164-99-6
• Molecular Formula: C₁₈H₂₈S
• Molecular Weight: 276.486
• Mol file: 66164-99-6.mol

Synonyms:(E)-2-dodecenyl phenyl sulphide

Chemical Property of (E)-2-dodecenyl phenyl sulphide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-2-dodecenyl phenyl sulphide

There total 1 articles about (E)-2-dodecenyl phenyl sulphide 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%

(2E)-dodec-2-en-1-ol (22104-81-0,69064-36-4,69064-37-5) + phenyl thiocyanate (5285-87-0) → (E)-2-dodecenyl phenyl sulphide (66164-99-6)

Guidance literature:

With tributylphosphine; In tetrahydrofuran; at -20 - 20 ℃;

DOI:10.1021/jo005602f

Reference yield: 94.0%

(E)-2-dodecenyl phenyl sulphide (66164-99-6) + Methanesulfonic acid (1R,2R,3S)-2-benzyloxy-1-benzyloxymethyl-3-methanesulfonyloxy-pent-4-enyl ester (185681-39-4) → (2R,3R,4E,8E)-1,3-di-O-benzyl-2-O-methylsulfonyl-7-(phenylthio)-4,8-octadecadiene-1,2,3-triol (316811-28-6)

Guidance literature:

(E)-2-dodecenyl phenyl sulphide; With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 ℃; for 2h;

Methanesulfonic acid (1R,2R,3S)-2-benzyloxy-1-benzyloxymethyl-3-methanesulfonyloxy-pent-4-enyl ester; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 ℃; for 0.5h; Further stages.;

DOI:10.1021/jo005602f

Reference yield:

(E)-2-dodecenyl phenyl sulphide (66164-99-6) → (2S,3R,4E,8E)-2-amino-1,3-di-O-benzyl-7-(phenylthio)-4,8-octadecadiene-1,3-diol (316811-31-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

1.2: 94 percent / CuCN*2LiCl / tetrahydrofuran; hexane; hexamethylphosphoric acid triamide / 0.5 h / -78 °C

2.1: 81 percent / sodium azide / dimethylformamide / 24 h / 100 °C

3.1: 100 percent / lithium aluminum hydride / diethyl ether / 12 h / 20 °C

With lithium aluminium tetrahydride; n-butyllithium; sodium azide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; N,N-dimethyl-formamide;

DOI:10.1021/jo005602f

upstream raw materials:

(2E)-dodec-2-en-1-ol

phenyl thiocyanate

Downstream raw materials:

(2R,3R,4E,8E)-1,3-di-O-benzyl-2-O-methylsulfonyl-7-(phenylthio)-4,8-octadecadiene-1,2,3-triol

(2S,3R,4E,8E)-2-amino-1,3-di-O-benzyl-7-(phenylthio)-4,8-octadecadiene-1,3-diol

(2S,3R,4E,8E)-2-azido-1,3-di-O-benzyl-7-(phenylthio)-4,8-octadecadiene-1,3-diol

Refernces