(1R,4S)-3-Acetoxy-bicyclo[2.2.1]hept-5-ene-2,2-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester

Base Information

• Chemical Name: (1R,4S)-3-Acetoxy-bicyclo[2.2.1]hept-5-ene-2,2-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester
• CAS No.: 111998-73-3
• Molecular Formula: C₃₁H₄₈O₆
• Molecular Weight: 516.719
• Mol file: 111998-73-3.mol

Synonyms:

Chemical Property of (1R,4S)-3-Acetoxy-bicyclo[2.2.1]hept-5-ene-2,2-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S)-3-Acetoxy-bicyclo[2.2.1]hept-5-ene-2,2-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester

There total 13 articles about (1R,4S)-3-Acetoxy-bicyclo[2.2.1]hept-5-ene-2,2-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester 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: 98.0%

Di-l-menthyl acetoxymethylenemalonate (111998-72-2) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → di-l-menthyl 3-acetoxybicyclo-<2.2.1>hept-5-ene-2,2-dicarboxylate (111998-73-3,112066-84-9,129312-72-7)

Guidance literature:

With lithium perchlorate; In diethyl ether; for 24h; Ambient temperature;

DOI:10.1248/cpb.40.1737

Reference yield: 83.0%

Di-l-menthyl acetoxymethylenemalonate (111998-72-2) + cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) → (1R,4S)-3-Acetoxy-bicyclo[2.2.1]hept-5-ene-2,2-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester (111998-73-3,112066-84-9,129312-72-7)

Guidance literature:

With titanium tetrachloride; at -78 ℃;

DOI:10.1021/jo00236a057

Reference yield:

(1S,2R,5S)-(+)-menthol (15356-60-2) → di-l-menthyl 3-endo-acetoxybicyclo<2.2.1>hept-5-ene-2,2-dicarboxylate (111998-73-3,112066-84-9,129312-72-7)

Guidance literature:

Multi-step reaction with 4 steps

1: benzene / 2 h / 55 °C

2: DCC / benzene / 2 h / Ambient temperature

3: pyridine / benzene / 12 h / Ambient temperature

4: TiCl₄ / 4 h / -78 °C

With pyridine; dicyclohexyl-carbodiimide; titanium tetrachloride; In benzene;

upstream raw materials:

Di-l-menthyl acetoxymethylenemalonate

cyclopenta-1,3-diene

di-l-menthyl 2-acetoxymethylenemalonate

(1S,2R,5S)-(+)-menthol

Downstream raw materials:

(1S,3R,4R)-3-Acetoxy-bicyclo[2.2.1]heptane-2,2-dicarboxylic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester

di-l-menthyl 3-endo-acetoxybicyclo<2.2.1>heptane-2,2-dicarboxylate

di-l-menthyl 3-exo-acetoxybicyclo<2.2.1>heptane-2,2-dicarboxylate

di-l-menthyl 3-exo-acetoxy-5,6-exo-dihydroxybicyclo<2.2.1>heptane-2,2-dicarboxylate