(1R,2S,4S)-benzyl 3-methylenebicyclo[2.2.1]hept-5-ene-2-carboxylate

Base Information

• Chemical Name: (1R,2S,4S)-benzyl 3-methylenebicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS No.: 1220882-03-0
• Molecular Formula: C₁₆H₁₆O₂
• Molecular Weight: 240.302
• Mol file: 1220882-03-0.mol

Synonyms:(1R,2S,4S)-benzyl 3-methylenebicyclo[2.2.1]hept-5-ene-2-carboxylate

Chemical Property of (1R,2S,4S)-benzyl 3-methylenebicyclo[2.2.1]hept-5-ene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,4S)-benzyl 3-methylenebicyclo[2.2.1]hept-5-ene-2-carboxylate

There total 1 articles about (1R,2S,4S)-benzyl 3-methylenebicyclo[2.2.1]hept-5-ene-2-carboxylate 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:

cyclopenta-1,3-diene (542-92-7,25568-84-7,7313-32-8) + buta-2,3-dienoic acid benzyl ester (187661-86-5) → (1R,2S,4S)-benzyl 3-methylenebicyclo[2.2.1]hept-5-ene-2-carboxylate (1220882-03-0) + (1S,2R,4R)-benzyl 3-methylenebicyclo[2.2.1]hept-5-ene-2-carboxylate

Guidance literature:

With C₂₄H₂₄AlBBr₃NO; In dichloromethane; 1,1-dibromomethane; at -90 ℃; for 3.5h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol1004802

Reference yield: 91.0%

2,3-Dichloroprop-1-ene (78-88-6) + (1R,2S,4S)-benzyl 3-methylenebicyclo[2.2.1]hept-5-ene-2-carboxylate (1220882-03-0) → (1R,2S,4S)-benzyl 2-(2-chloroallyl)-3-methylenebicyclo[2.2.1]hept-5-ene-2-carboxylate (1220881-95-7)

Guidance literature:

(1R,2S,4S)-benzyl 3-methylenebicyclo[2.2.1]hept-5-ene-2-carboxylate; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.516667h; Inert atmosphere;

2,3-Dichloroprop-1-ene; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 - 20 ℃; optical yield given as %de; Inert atmosphere;

DOI:10.1021/ol1004802

Reference yield: 90.0%

(1R,2S,4S)-benzyl 3-methylenebicyclo[2.2.1]hept-5-ene-2-carboxylate (1220882-03-0) + methyl iodide (74-88-4) → (1R,2S,4S)-benzyl 2-methyl-3-methylenebicyclo[2.2.1]hept-5-ene-2-carboxylate (1220881-94-6) + (1R,2R,4S)-benzyl 2-methyl-3-methylenebicyclo[2.2.1]hept-5-ene-2-carboxylate (1220882-07-4)

Guidance literature:

(1R,2S,4S)-benzyl 3-methylenebicyclo[2.2.1]hept-5-ene-2-carboxylate; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.516667h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1021/ol1004802

upstream raw materials:

cyclopenta-1,3-diene

buta-2,3-dienoic acid benzyl ester

Downstream raw materials:

(1R,2S,4S)-benzyl 2-(2-chloroallyl)-3-methylenebicyclo[2.2.1]hept-5-ene-2-carboxylate

(1R,2S,4S)-benzyl 2-methyl-3-methylenebicyclo[2.2.1]hept-5-ene-2-carboxylate

(1R,2R,4S)-benzyl 2-methyl-3-methylenebicyclo[2.2.1]hept-5-ene-2-carboxylate