8-phenylselanyl-9,10-bis-trimethylsilanylmethyl-tricyclo[4.2.2.0^1,6]dec-9-ene-7-carboxylic acid methyl ester

Base Information

• Chemical Name: 8-phenylselanyl-9,10-bis-trimethylsilanylmethyl-tricyclo[4.2.2.0^1,6]dec-9-ene-7-carboxylic acid methyl ester
• CAS No.: 499158-31-5
• Molecular Formula: C₂₆H₄₀O₂SeSi₂
• Molecular Weight: 519.733

Synonyms:8-phenylselanyl-9,10-bis-trimethylsilanylmethyl-tricyclo[4.2.2.0^1,6]dec-9-ene-7-carboxylic acid methyl ester

Chemical Property of 8-phenylselanyl-9,10-bis-trimethylsilanylmethyl-tricyclo[4.2.2.0^1,6]dec-9-ene-7-carboxylic acid methyl ester

Chemical Property:

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Technology Process of 8-phenylselanyl-9,10-bis-trimethylsilanylmethyl-tricyclo[4.2.2.0^1,6]dec-9-ene-7-carboxylic acid methyl ester

There total 5 articles about 8-phenylselanyl-9,10-bis-trimethylsilanylmethyl-tricyclo[4.2.2.0^1,6]dec-9-ene-7-carboxylic acid methyl 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:

4,5,6,7-tetrahydroindan-1-one (22118-00-9) → 8-phenylselanyl-9,10-bis-trimethylsilanylmethyl-tricyclo[4.2.2.01,6]dec-9-ene-7-carboxylic acid methyl ester (499158-31-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 18 percent / acetone / 2.5 h / -20 °C / UV-irradiation

2.1: MeONa / benzene / 17.5 h / 24 °C

3.1: 123 mg / TsN₃; Et₃N / CH₂Cl₂ / 22 h / 24 °C

4.1: 80 percent / Et₃N / 3 h / 5 °C

5.1: i-Pr₂NH; BuLi / hexane; tetrahydrofuran / 1.08 h / -78 - -40 °C

5.2: 79 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(trimethylsilyl)-2-butyne (21752-78-3) → 8-phenylselanyl-9,10-bis-trimethylsilanylmethyl-tricyclo[4.2.2.01,6]dec-9-ene-7-carboxylic acid methyl ester (499158-31-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 18 percent / acetone / 2.5 h / -20 °C / UV-irradiation

2.1: MeONa / benzene / 17.5 h / 24 °C

3.1: 123 mg / TsN₃; Et₃N / CH₂Cl₂ / 22 h / 24 °C

4.1: 80 percent / Et₃N / 3 h / 5 °C

5.1: i-Pr₂NH; BuLi / hexane; tetrahydrofuran / 1.08 h / -78 - -40 °C

5.2: 79 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-oxo-8,9-bis-trimethylsilanylmethyl-hexahydro-3a,7a-etheno-indene-2-carbaldehyde (499158-28-0) → 8-phenylselanyl-9,10-bis-trimethylsilanylmethyl-tricyclo[4.2.2.01,6]dec-9-ene-7-carboxylic acid methyl ester (499158-31-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 123 mg / TsN₃; Et₃N / CH₂Cl₂ / 22 h / 24 °C

2.1: 80 percent / Et₃N / 3 h / 5 °C

3.1: i-Pr₂NH; BuLi / hexane; tetrahydrofuran / 1.08 h / -78 - -40 °C

3.2: 79 percent / HMPA / hexane; tetrahydrofuran / 3 h / -78 - 20 °C

With n-butyllithium; 4-toluenesulfonyl azide; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; 2.1: photo-Wolf rearrangement;

DOI:10.1021/ja021206y

upstream raw materials:

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

1,4-bis(trimethylsilyl)-2-butyne

1-oxo-8,9-bis-trimethylsilanylmethyl-hexahydro-3a,7a-etheno-indene-2-carbaldehyde

8,9-bis-trimethylsilanylmethyl-hexahydro-3a,7a-etheno-inden-1-one

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