(1R,3aR,6aR)-octahydro-1-pentalenyl 2,4-dinitrobenzoate

Base Information

• Chemical Name: (1R,3aR,6aR)-octahydro-1-pentalenyl 2,4-dinitrobenzoate
• CAS No.: 177600-48-5
• Molecular Formula: C₁₅H₁₆N₂O₆
• Molecular Weight: 320.302
• Mol file: 177600-48-5.mol

Synonyms:(1R,3aR,6aR)-octahydro-1-pentalenyl 2,4-dinitrobenzoate

Chemical Property of (1R,3aR,6aR)-octahydro-1-pentalenyl 2,4-dinitrobenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3aR,6aR)-octahydro-1-pentalenyl 2,4-dinitrobenzoate

There total 4 articles about (1R,3aR,6aR)-octahydro-1-pentalenyl 2,4-dinitrobenzoate 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:

(1R,3aS,6aS)-octahydro-1-pentalenol (211872-47-8) + 2,4-dinitrobenzoic acid (610-30-0) → (1R,3aR,6aR)-octahydro-1-pentalenyl 2,4-dinitrobenzoate (177600-48-5) + (1S,3aS,6aS)-octahydro-1-pentalenyl 2,4-dinitrobenzoate

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 16h; Title compound not separated from byproducts.;

DOI:10.1021/ja027774v

Reference yield:

Cyclooctene oxide (286-62-4) + 2,4-dinitrobenzoic acid (610-30-0) → (1R,3aR,6aR)-octahydro-1-pentalenyl 2,4-dinitrobenzoate (177600-48-5) + (1S,3aS,6aS)-octahydro-1-pentalenyl 2,4-dinitrobenzoate

Guidance literature:

Cyclooctene oxide; With sec.-butyllithium; (-)-sparteine; In diethyl ether; cyclohexane; at -78 - 20 ℃; for 22h;

2,4-dinitrobenzoic acid; With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 64h; Title compound not separated from byproducts;

DOI:10.1016/j.tet.2003.09.024

Reference yield:

Cyclooctene oxide (286-62-4) → (1R,3aR,6aR)-octahydro-1-pentalenyl 2,4-dinitrobenzoate (177600-48-5)

Guidance literature:

Multi-step reaction with 2 steps

1: sec-BuLi; (-)-sparteine / diethyl ether / -78 - 20 °C

2: PPh₃; DEAD / 65 h / 20 °C

With sec.-butyllithium; triphenylphosphine; (-)-sparteine; diethylazodicarboxylate; In diethyl ether; 2: Mitsunobu reaction;

DOI:10.1016/S0040-4039(03)01677-0

upstream raw materials:

(-)-cis-bicyclo<3.3.0>octan-endo-2-ol

2,4-dinitrobenzoic acid

Cyclooctene oxide

(1R,3aS,6aS)-octahydro-1-pentalenol

Downstream raw materials:

tert-butyl (1S,3aR,6aR)-octahydro-1-pentalenyl-[(4-methylphenyl)sulfonyl]carbamate