2-Pentenoic acid, 2-methyl-5-[(1S,6R)-6-[(4-methylphenyl)thio]bicyclo[4.1.0]hept-1-yl]-, methyl ester, (2E)-

Base Information

• Chemical Name: 2-Pentenoic acid, 2-methyl-5-[(1S,6R)-6-[(4-methylphenyl)thio]bicyclo[4.1.0]hept-1-yl]-, methyl ester, (2E)-
• CAS No.: 180524-20-3
• Molecular Formula: C21H28O2S
• Molecular Weight: 344.518
• Mol file: 180524-20-3.mol

Synonyms:

Chemical Property of 2-Pentenoic acid, 2-methyl-5-[(1S,6R)-6-[(4-methylphenyl)thio]bicyclo[4.1.0]hept-1-yl]-, methyl ester, (2E)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Pentenoic acid, 2-methyl-5-[(1S,6R)-6-[(4-methylphenyl)thio]bicyclo[4.1.0]hept-1-yl]-, methyl ester, (2E)-

There total 2 articles about 2-Pentenoic acid, 2-methyl-5-[(1S,6R)-6-[(4-methylphenyl)thio]bicyclo[4.1.0]hept-1-yl]-, methyl ester, (2E)- 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: 90.0%

3-<(1S,6R)-6-(p-tolylthio)bicyclo<4.1.0>heptan-1-yl>propanal (180524-19-0) + methyl 2-(triphenylphosphoranylidene)propionate (2605-68-7) → (E)-2-Methyl-5-((1S,6R)-6-p-tolylsulfanyl-bicyclo[4.1.0]hept-1-yl)-pent-2-enoic acid methyl ester (180524-20-3)

Guidance literature:

In toluene; Heating;

DOI:10.1039/CC9960001655

Reference yield:

3-<(1S,6R)-6-(p-tolylthio)bicyclo<4.1.0>hept-1-yl>propanol (155501-29-4) → (E)-2-Methyl-5-((1S,6R)-6-p-tolylsulfanyl-bicyclo[4.1.0]hept-1-yl)-pent-2-enoic acid methyl ester (180524-20-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -50 deg C

2: 90 percent / toluene / Heating

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In toluene;

DOI:10.1039/CC9960001655

Reference yield:

(E)-2-Methyl-5-((1S,6R)-6-p-tolylsulfanyl-bicyclo[4.1.0]hept-1-yl)-pent-2-enoic acid methyl ester (180524-20-3) → C20H26O3S (186357-52-8)

Guidance literature:

Multi-step reaction with 6 steps

2: 97 percent / MCPBA / CH₂Cl₂ / 0 °C

3: 85 percent / DIBAL-H / CH₂Cl₂ / -78 °C

4: 87 percent / Ac₂O, pyridine

5: Pd(acac)2, PBu₃, HCO₂H*Et₃N / benzene / 2 h / 60 °C

6: t-BuOOH, KH / tetrahydrofuran / 1.) -78 deg C, 2.) 0 deg c

With pyridine; tert.-butylhydroperoxide; palladium(II) acetylacetonate; tributylphosphine; acetic anhydride; potassium hydride; diisobutylaluminium hydride; triethylammonium formate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1039/CC9960001655

upstream raw materials:

3-<(1S,6R)-6-(p-tolylthio)bicyclo<4.1.0>heptan-1-yl>propanal

methyl 2-(triphenylphosphoranylidene)propionate

3-<(1S,6R)-6-(p-tolylthio)bicyclo<4.1.0>hept-1-yl>propanol

Downstream raw materials:

2-[(S)-6-p-Tolylsulfanyl-spiro[4.5]dec-6-en-(2E)-ylidene]-propionic acid methyl ester

C₂₀H₂₆O₃S

2-[(S)-6-(Toluene-4-sulfonyl)-spiro[4.5]dec-6-en-(2E)-ylidene]-propan-1-ol

2-[(S)-6-(Toluene-4-sulfonyl)-spiro[4.5]dec-6-en-(2E)-ylidene]-propionic acid methyl ester

Refernces