6-exo-3-oxo-6-(phenylseleno)bicyclo<3.3.1>nonane-1,4-dicarboxylic acid 1-methyl 4-ethyl diester

Base Information

• Chemical Name: 6-exo-3-oxo-6-(phenylseleno)bicyclo<3.3.1>nonane-1,4-dicarboxylic acid 1-methyl 4-ethyl diester
• CAS No.: 114584-48-4
• Molecular Formula: C₂₀H₂₄O₅Se
• Molecular Weight: 423.368

Synonyms:6-exo-3-oxo-6-(phenylseleno)bicyclo<3.3.1>nonane-1,4-dicarboxylic acid 1-methyl 4-ethyl diester

Chemical Property of 6-exo-3-oxo-6-(phenylseleno)bicyclo<3.3.1>nonane-1,4-dicarboxylic acid 1-methyl 4-ethyl diester

Chemical Property:

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Technology Process of 6-exo-3-oxo-6-(phenylseleno)bicyclo<3.3.1>nonane-1,4-dicarboxylic acid 1-methyl 4-ethyl diester

There total 2 articles about 6-exo-3-oxo-6-(phenylseleno)bicyclo<3.3.1>nonane-1,4-dicarboxylic acid 1-methyl 4-ethyl diester 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:

(1S,4S,5S,6R)-6-Chloro-3-oxo-bicyclo[3.3.1]nonane-1,4-dicarboxylic acid 4-ethyl ester 1-methyl ester (114584-47-3) → 6-exo-3-oxo-6-(phenylseleno)bicyclo<3.3.1>nonane-1,4-dicarboxylic acid 1-methyl 4-ethyl diester (114584-48-4)

Guidance literature:

Multi-step reaction with 2 steps

1: DBU / CH₂Cl₂ / 4 h / 21 °C

2: tetrahydrofuran / 0.5 h / 0 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00249a013

Reference yield:

lithium phenylselenide (52251-58-8) + 3-oxotricyclo<3.3.1.02,8>nonane-2,5-dicarboxylic acid 2-ethyl 5-methyl diester (114595-86-7) → 6-exo-3-oxo-6-(phenylseleno)bicyclo<3.3.1>nonane-1,4-dicarboxylic acid 1-methyl 4-ethyl diester (114584-48-4)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 0.5h; Yield given;

DOI:10.1021/jo00249a013

Reference yield: 74.0%

6-exo-3-oxo-6-(phenylseleno)bicyclo<3.3.1>nonane-1,4-dicarboxylic acid 1-methyl 4-ethyl diester (114584-48-4) → methyl 6-exo-3-oxo-6-(phenylseleno)bicyclo<3.3.1>nonane-1-dicarboxylate (114584-49-5)

Guidance literature:

With water; dimethyl sulfoxide; at 150 ℃; for 3.25h;

DOI:10.1021/jo00249a013

upstream raw materials:

lithium phenylselenide

3-oxotricyclo<3.3.1.0^2,8>nonane-2,5-dicarboxylic acid 2-ethyl 5-methyl diester

(1S,4S,5S,6R)-6-Chloro-3-oxo-bicyclo[3.3.1]nonane-1,4-dicarboxylic acid 4-ethyl ester 1-methyl ester

Downstream raw materials:

methyl 6-exo-3-oxo-6-(phenylseleno)bicyclo<3.3.1>nonane-1-dicarboxylate

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