6,8,13,15-Tetrahydro-17-oxo-7,14-methanobenzo[6,7]cyclodeca[1,2-b]naphthalene-7,14-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: 6,8,13,15-Tetrahydro-17-oxo-7,14-methanobenzo[6,7]cyclodeca[1,2-b]naphthalene-7,14-dicarboxylic acid dimethyl ester
• CAS No.: 108395-67-1
• Molecular Formula: C₂₇H₂₄O₅
• Molecular Weight: 428.485
• Mol file: 108395-67-1.mol

Synonyms:6,8,13,15-Tetrahydro-17-oxo-7,14-methanobenzo[6,7]cyclodeca[1,2-b]naphthalene-7,14-dicarboxylic acid dimethyl ester

Chemical Property of 6,8,13,15-Tetrahydro-17-oxo-7,14-methanobenzo[6,7]cyclodeca[1,2-b]naphthalene-7,14-dicarboxylic acid dimethyl ester

Chemical Property:

• Melting Point: 242 - 243 °C (benzene)
• PSA: 69.67000
• LogP: 3.62510

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6,8,13,15-Tetrahydro-17-oxo-7,14-methanobenzo[6,7]cyclodeca[1,2-b]naphthalene-7,14-dicarboxylic acid dimethyl ester

There total 5 articles about 6,8,13,15-Tetrahydro-17-oxo-7,14-methanobenzo[6,7]cyclodeca[1,2-b]naphthalene-7,14-dicarboxylic acid dimethyl 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: 61.0%

dimethyl 1,2,4,5-tetrahydro-3-oxonaphtho<2,3-d>cycloheptene-2,4-dicarboxylate (122761-72-2) + α,α'-dibromo-o-xylene (91-13-4) → dimethyl benzonaphtho<2,3-h>-11-oxobicyclo<4.4.1>undeca-3,8-diene-1,6-dicarboxylate (108395-67-1)

Guidance literature:

With sodium hydroxide; tetrabutyl-ammonium chloride;

DOI:10.1021/jo00389a004

Reference yield: 60.0%

2,3-di(bromomethyl)naphthalene (38998-33-3) + dimethyl 1,2,4,5-tetrahydro-3-oxobenzocycloheptene-2,4-dicarboxylate (24790-66-7) → dimethyl benzonaphtho<2,3-h>-11-oxobicyclo<4.4.1>undeca-3,8-diene-1,6-dicarboxylate (108395-67-1)

Guidance literature:

With sodium hydroxide; tetrabutyl-ammonium chloride; In dichloromethane; for 25h; Ambient temperature;

DOI:10.1021/jo00389a004

Reference yield:

3-oxopentanedioic acid dimethyl ester (1830-54-2) → dimethyl benzonaphtho<2,3-h>-11-oxobicyclo<4.4.1>undeca-3,8-diene-1,6-dicarboxylate (108395-67-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 49 percent / Bu₄NBr, 8percent aq. NaHCO₃ / CH₂Cl₂ / 40 h

2: 61 percent / Bu₄NCl, 23 percent aq. NaOH

With sodium hydroxide; tetrabutylammomium bromide; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; In dichloromethane;

DOI:10.1021/jo00389a004

upstream raw materials:

2,3-di(bromomethyl)naphthalene

dimethyl 1,2,4,5-tetrahydro-3-oxobenzocycloheptene-2,4-dicarboxylate

dimethyl 1,2,4,5-tetrahydro-3-oxonaphtho<2,3-d>cycloheptene-2,4-dicarboxylate

α,α'-dibromo-o-xylene

Downstream raw materials:

<3.3>benzonaphthophane

benzonaphtho<2,3-h>bicyclo<4.4.1>undeca-3,8-dien-11-one

Refernces