Bicyclo[3.2.0]hept-6-ene, 2-methyl-1-(2-methyl-1-propen-1-yl)-7-(phenylthio)-, (1S,2S,5S)-

Base Information

• Chemical Name: Bicyclo[3.2.0]hept-6-ene, 2-methyl-1-(2-methyl-1-propen-1-yl)-7-(phenylthio)-, (1S,2S,5S)-
• CAS No.: 925413-83-8
• Molecular Formula: C18H22S
• Molecular Weight: 270.439
• Mol file: 925413-83-8.mol

Synonyms:

Chemical Property of Bicyclo[3.2.0]hept-6-ene, 2-methyl-1-(2-methyl-1-propen-1-yl)-7-(phenylthio)-, (1S,2S,5S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Bicyclo[3.2.0]hept-6-ene, 2-methyl-1-(2-methyl-1-propen-1-yl)-7-(phenylthio)-, (1S,2S,5S)-

There total 7 articles about Bicyclo[3.2.0]hept-6-ene, 2-methyl-1-(2-methyl-1-propen-1-yl)-7-(phenylthio)-, (1S,2S,5S)- 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: 86.0%

(1S,2S,5S)-1-formyl-2-methyl-7-phenylsulfanylbicyclo[3.2.0]hept-6-ene (925413-82-7) + isopropyltriphenylphosphonium iodide (24470-78-8) → (1S,2S,5S)-2-methyl-1-(2-methyl-1-propenyl)-7-phenylsulfanylbicyclo[3.2.0]hept-6-ene (925413-83-8)

Guidance literature:

isopropyltriphenylphosphonium iodide; With n-butyllithium; In tetrahydrofuran; hexane; at 20 ℃; for 0.5h;

(1S,2S,5S)-1-formyl-2-methyl-7-phenylsulfanylbicyclo[3.2.0]hept-6-ene; In tetrahydrofuran; hexane; at -78 ℃; for 2h;

DOI:10.1016/j.tet.2006.10.072

Reference yield:

(1R,5S)-1-hydroxymethyl-2-methylene-7-phenylsulfanylbicyclo[3.2.0]hept-6-ene (925413-80-5) → (1S,2S,5S)-2-methyl-1-(2-methyl-1-propenyl)-7-phenylsulfanylbicyclo[3.2.0]hept-6-ene (925413-83-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: H₂ / tris(triphenylphosphine)rhodium chloride / CH₂Cl₂ / 4 h / 20 °C

2.1: 88 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 20 °C

3.2: 86 percent / tetrahydrofuran; hexane / 2 h / -78 °C

With n-butyllithium; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; Wilkinson's catalyst; In tetrahydrofuran; hexane; dichloromethane; 3.2: Wittig reaction;

DOI:10.1016/j.tet.2006.10.072

Reference yield:

(1R,5S)-1-methoxycarbonyl-2-methylene-7-phenylsulfanylbicyclo[3.2.0]hept-6-ene (925413-79-2) → (1S,2S,5S)-2-methyl-1-(2-methyl-1-propenyl)-7-phenylsulfanylbicyclo[3.2.0]hept-6-ene (925413-83-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 98 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

2.1: H₂ / tris(triphenylphosphine)rhodium chloride / CH₂Cl₂ / 4 h / 20 °C

3.1: 88 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 20 °C

4.2: 86 percent / tetrahydrofuran; hexane / 2 h / -78 °C

With lithium aluminium tetrahydride; n-butyllithium; hydrogen; sodium hydrogencarbonate; Dess-Martin periodane; Wilkinson's catalyst; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 4.2: Wittig reaction;

DOI:10.1016/j.tet.2006.10.072

upstream raw materials:

(1S,2S,5S)-1-formyl-2-methyl-7-phenylsulfanylbicyclo[3.2.0]hept-6-ene

isopropyltriphenylphosphonium iodide

(1S,2S,5S)-1-hydroxymethyl-2-methyl-7-phenylsulfanylbicyclo[3.2.0]hept-6-ene

(1R,5S)-1-hydroxymethyl-2-methylene-7-phenylsulfanylbicyclo[3.2.0]hept-6-ene