methyl 4-(9α-cyano-9-oxo-2,3,9,9α-tetrahydro-1H-cyclopenta[b]naphthalen-4-yl)benzoate

Base Information

• Chemical Name: methyl 4-(9α-cyano-9-oxo-2,3,9,9α-tetrahydro-1H-cyclopenta[b]naphthalen-4-yl)benzoate
• CAS No.: 1415336-94-5
• Molecular Formula: C₂₂H₁₇NO₃
• Molecular Weight: 343.382
• Mol file: 1415336-94-5.mol

Synonyms:methyl 4-(9α-cyano-9-oxo-2,3,9,9α-tetrahydro-1H-cyclopenta[b]naphthalen-4-yl)benzoate

Chemical Property of methyl 4-(9α-cyano-9-oxo-2,3,9,9α-tetrahydro-1H-cyclopenta[b]naphthalen-4-yl)benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4-(9α-cyano-9-oxo-2,3,9,9α-tetrahydro-1H-cyclopenta[b]naphthalen-4-yl)benzoate

There total 3 articles about methyl 4-(9α-cyano-9-oxo-2,3,9,9α-tetrahydro-1H-cyclopenta[b]naphthalen-4-yl)benzoate 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: 89.0%

methyl 4-(6-cyano-7-oxo-7-phenylhept-1-ynyl)benzoate (1415336-90-1) → methyl 4-(9α-cyano-9-oxo-2,3,9,9α-tetrahydro-1H-cyclopenta[b]naphthalen-4-yl)benzoate (1415336-94-5)

Guidance literature:

With copper(l) iodide; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1002/adsc.201300107

Reference yield:

methyl 4-(5-oxopent-1-yn-1-yl)benzoate (1415336-96-7) → methyl 4-(9α-cyano-9-oxo-2,3,9,9α-tetrahydro-1H-cyclopenta[b]naphthalen-4-yl)benzoate (1415336-94-5)

Guidance literature:

Multi-step reaction with 2 steps

1: L-proline; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate / ethanol / 16 h / 25 °C / Inert atmosphere

2: tetra-(n-butyl)ammonium iodide; tert.-butylhydroperoxide / water; benzene / 1 h / 80 °C / Inert atmosphere

With tert.-butylhydroperoxide; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; tetra-(n-butyl)ammonium iodide; L-proline; In ethanol; water; benzene; 1: |Knoevenagel Condensation;

DOI:10.1021/ol3028972

Reference yield:

2-benzoylhept-6-ynenitrile (1092110-31-0) + methyl 4-iodobenzoate (619-44-3) → methyl 4-(9α-cyano-9-oxo-2,3,9,9α-tetrahydro-1H-cyclopenta[b]naphthalen-4-yl)benzoate (1415336-94-5)

Guidance literature:

With pyrrolidine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; at 20 ℃; for 3.5h; Reagent/catalyst; Solvent; Temperature; Concentration;

DOI:10.1002/adsc.201300107

upstream raw materials:

methyl 4-(6-cyano-7-oxo-7-phenylhept-1-ynyl)benzoate

methyl 4-(5-oxopent-1-yn-1-yl)benzoate

2-benzoylhept-6-ynenitrile

methyl 4-iodobenzoate