dimenthyl (1R,2S,3R)-2-(4-methylpent-3-enyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Base Information

• Chemical Name: dimenthyl (1R,2S,3R)-2-(4-methylpent-3-enyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate
• CAS No.: 457930-97-1
• Molecular Formula: C₃₅H₅₆O₄
• Molecular Weight: 540.827
• Mol file: 457930-97-1.mol

Synonyms:dimenthyl (1R,2S,3R)-2-(4-methylpent-3-enyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Chemical Property of dimenthyl (1R,2S,3R)-2-(4-methylpent-3-enyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimenthyl (1R,2S,3R)-2-(4-methylpent-3-enyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate

There total 3 articles about dimenthyl (1R,2S,3R)-2-(4-methylpent-3-enyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate 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: 61.0%

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + dimenthyl 2-(4-methylpent-3-enyl)maleate (457930-96-0) → (1S,2R,3S,4R)-2-(4-Methyl-pent-3-enyl)-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester + dimenthyl (1R,2S,3R)-2-(4-methylpent-3-enyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (457930-97-1)

Guidance literature:

With diethylaluminium chloride; In dichloromethane; toluene; at -30 ℃; for 14h;

DOI:10.1016/S0957-4166(02)00194-5

Reference yield:

4-methyl-3-pentenylmagnesium bromide (37586-57-5) → dimenthyl (1R,2S,3R)-2-(4-methylpent-3-enyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (457930-97-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: CuBr(Me₂S) / tetrahydrofuran / 0.67 h / -78 °C

1.2: 97 percent / tetrahydrofuran / 4 h / -78 °C

2.1: 61 percent / diethylaluminium chloride / CH₂Cl₂; toluene / 14 h / -30 °C

With copper(I) bromide dimethylsulfide complex; diethylaluminium chloride; In tetrahydrofuran; dichloromethane; toluene; 2.1: Diels-Alder reaction;

DOI:10.1016/S0957-4166(02)00194-5

Reference yield:

bis((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) but-2-ynedioate (65018-53-3) → dimenthyl (1R,2S,3R)-2-(4-methylpent-3-enyl)bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate (457930-97-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: CuBr(Me₂S) / tetrahydrofuran / 0.67 h / -78 °C

1.2: 97 percent / tetrahydrofuran / 4 h / -78 °C

2.1: 61 percent / diethylaluminium chloride / CH₂Cl₂; toluene / 14 h / -30 °C

With copper(I) bromide dimethylsulfide complex; diethylaluminium chloride; In tetrahydrofuran; dichloromethane; toluene; 2.1: Diels-Alder reaction;

DOI:10.1016/S0957-4166(02)00194-5

upstream raw materials:

cyclopenta-1,3-diene

dimenthyl 2-(4-methylpent-3-enyl)maleate

4-methyl-3-pentenylmagnesium bromide

bis((1R,2S,5R)-2-isopropyl-5-methylcyclohexyl) but-2-ynedioate