8-phenylselanyl-9,10-bis-[(triisopropylsilanyl)-methyl]-tricyclo[4.2.2.0^1,6]dec-9-ene-7-carboxylic acid dimethylamide

Base Information

• Chemical Name: 8-phenylselanyl-9,10-bis-[(triisopropylsilanyl)-methyl]-tricyclo[4.2.2.0^1,6]dec-9-ene-7-carboxylic acid dimethylamide
• CAS No.: 499158-35-9
• Molecular Formula: C₃₉H₆₇NOSeSi₂
• Molecular Weight: 701.098

Synonyms:8-phenylselanyl-9,10-bis-[(triisopropylsilanyl)-methyl]-tricyclo[4.2.2.0^1,6]dec-9-ene-7-carboxylic acid dimethylamide

Chemical Property of 8-phenylselanyl-9,10-bis-[(triisopropylsilanyl)-methyl]-tricyclo[4.2.2.0^1,6]dec-9-ene-7-carboxylic acid dimethylamide

Chemical Property:

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Technology Process of 8-phenylselanyl-9,10-bis-[(triisopropylsilanyl)-methyl]-tricyclo[4.2.2.0^1,6]dec-9-ene-7-carboxylic acid dimethylamide

There total 6 articles about 8-phenylselanyl-9,10-bis-[(triisopropylsilanyl)-methyl]-tricyclo[4.2.2.0^1,6]dec-9-ene-7-carboxylic acid dimethylamide 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: 31.0%

Phenylselenyl bromide (34837-55-3) + 9,10-bis-[(triisopropylsilanyl)-methyl]-tricyclo[4.2.2.01,6]dec-9-ene-7-carboxylic acid dimethylamide (499158-34-8) → 8-phenylselanyl-9,10-bis-[(triisopropylsilanyl)-methyl]-tricyclo[4.2.2.01,6]dec-9-ene-7-carboxylic acid dimethylamide (499158-35-9)

Guidance literature:

9,10-bis-[(triisopropylsilanyl)-methyl]-tricyclo[4.2.2.0^1,6]dec-9-ene-7-carboxylic acid dimethylamide; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 - -40 ℃; for 4h;

Phenylselenyl bromide; With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 3h; Further stages.;

DOI:10.1021/ja021206y

Reference yield:

4,5,6,7-tetrahydroindan-1-one (22118-00-9) → 8-phenylselanyl-9,10-bis-[(triisopropylsilanyl)-methyl]-tricyclo[4.2.2.01,6]dec-9-ene-7-carboxylic acid dimethylamide (499158-35-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 3.2 percent / acetone / 10 h / -20 °C / UV-irradiation

2.1: MeONa / benzene / 24 h / 24 °C

3.1: 29 mg / TsN₃; Et₃N / CH₂Cl₂ / 24 h / 24 °C

4.1: 66 percent / 6 h / -20 °C / UV-irradiation

5.1: i-Pr₂NH; BuLi / hexane; tetrahydrofuran / 4 h / -78 - -40 °C

5.2: 31 percent / HMPA / hexane; tetrahydrofuran / 3 h / -78 - 20 °C

With n-butyllithium; 4-toluenesulfonyl azide; sodium methylate; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; acetone; benzene; 4.1: photo-Wolf rearrangement;

DOI:10.1021/ja021206y

Reference yield:

1,4-bis(tri-i-propylsilyl)-2-butyne → 8-phenylselanyl-9,10-bis-[(triisopropylsilanyl)-methyl]-tricyclo[4.2.2.01,6]dec-9-ene-7-carboxylic acid dimethylamide (499158-35-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 3.2 percent / acetone / 10 h / -20 °C / UV-irradiation

2.1: MeONa / benzene / 24 h / 24 °C

3.1: 29 mg / TsN₃; Et₃N / CH₂Cl₂ / 24 h / 24 °C

4.1: 66 percent / 6 h / -20 °C / UV-irradiation

5.1: i-Pr₂NH; BuLi / hexane; tetrahydrofuran / 4 h / -78 - -40 °C

5.2: 31 percent / HMPA / hexane; tetrahydrofuran / 3 h / -78 - 20 °C

With n-butyllithium; 4-toluenesulfonyl azide; sodium methylate; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; acetone; benzene; 4.1: photo-Wolf rearrangement;

DOI:10.1021/ja021206y

upstream raw materials:

Phenylselenyl bromide

9,10-bis-[(triisopropylsilanyl)-methyl]-tricyclo[4.2.2.0^1,6]dec-9-ene-7-carboxylic acid dimethylamide

4,5,6,7-tetrahydroindan-1-one

8,9-bis-[(triisopropylsilanyl)-methyl]-hexahydro-3a,7a-etheno-inden-1-one

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