7-Phenylselanyl-tricyclo[4.2.2.0^1,6]deca-2,4,9-triene-7-carboxylic acid methyl ester

Base Information

• Chemical Name: 7-Phenylselanyl-tricyclo[4.2.2.0^1,6]deca-2,4,9-triene-7-carboxylic acid methyl ester
• CAS No.: 76713-76-3
• Molecular Formula: C₁₈H₁₆O₂Se
• Molecular Weight: 343.284

Synonyms:7-Phenylselanyl-tricyclo[4.2.2.0^1,6]deca-2,4,9-triene-7-carboxylic acid methyl ester

Chemical Property of 7-Phenylselanyl-tricyclo[4.2.2.0^1,6]deca-2,4,9-triene-7-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-Phenylselanyl-tricyclo[4.2.2.0^1,6]deca-2,4,9-triene-7-carboxylic acid methyl ester

There total 37 articles about 7-Phenylselanyl-tricyclo[4.2.2.0^1,6]deca-2,4,9-triene-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:

1,4-cyclohexadiene-1,2-dicarboxylic anhydride (4773-89-1) → 7-Phenylselanyl-tricyclo[4.2.2.01,6]deca-2,4,9-triene-7-carboxylic acid methyl ester (76713-76-3)

Guidance literature:

Multi-step reaction with 13 steps

1: Ph₂C=O / Irradiation

2: LiAlH₄

3: p-TsOH

4: Na/NH₃

5: 60percent aq. AcOH

6: pyridine

7: 1.) MeSCH₂S(O)Me, 2.) BuLi, 3.) H₂SO₄

8: C₅H₅NHBr₃, pyridine / CH₂Cl₂

9: LiCl, Li₂CO₃, HMPA

10: EtONa / benzene

11: p-TsN₃, triethylamine / diethyl ether

12: Irradiation

13: 1.) LDA, 2.) HMPA / 1.) THF, -78 deg C, 20 min, 2.) THF, a) -78 deg C, 20 min, b) -40 deg C, 1 h

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; n-butyllithium; 4-toluenesulfonyl azide; benzophenone; sulfuric acid; ammonia; sodium ethanolate; sodium; lithium carbonate; toluene-4-sulfonic acid; acetic acid; pyridinium hydrobromide perbromide; triethylamine; lithium chloride; lithium diisopropyl amide; methyl methylsulfinylmethyl sulfide; In diethyl ether; dichloromethane; benzene;

Reference yield:

Bicyclo<4.3.0>nona-1(6),3-dien-7-one (75781-80-5) → 7-Phenylselanyl-tricyclo[4.2.2.01,6]deca-2,4,9-triene-7-carboxylic acid methyl ester (76713-76-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 26 h / Irradiation

2: NaBH₄ / methanol / 16 h / Ambient temperature

3: Na/NH₃ / diethyl ether / 3.5 h

4: 1.) DMSO, oxalyl chloride, 2.) triethylamine / 1.) CH₂Cl₂, -78 deg, 2.5 h, 2.) CH₂Cl₂, -78 deg C, 20 min

5: MeONa / benzene / 18.5 h / 12 °C

6: TsN₃, triethylamine / CH₂Cl₂ / 24 h / 20 °C

7: 86 percent / triethylamine / methanol / 24 h / Irradiation

8: pyridine, pyridinium bromide perbromide / CH₂Cl₂ / 3.5 h / 0 °C

9: LiCl, Li₂CO₃, HMPA / 42 h / 40 - 100 °C

10: 1.) LDA, 2.) HMPA / 1.) THF, -78 deg C, 20 min, 2.) THF, a) -78 deg C, 20 min, b) -40 deg C, 1 h

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; 4-toluenesulfonyl azide; oxalyl dichloride; ammonia; sodium methylate; pyridinium hydrobromide perbromide; sodium; lithium carbonate; dimethyl sulfoxide; triethylamine; lithium chloride; lithium diisopropyl amide; In methanol; diethyl ether; dichloromethane; benzene;

Reference yield:

2,3,4,7-Tetrahydro-3a,7a-etheno-inden-1-one (124944-22-5) → 7-Phenylselanyl-tricyclo[4.2.2.01,6]deca-2,4,9-triene-7-carboxylic acid methyl ester (76713-76-3)

Guidance literature:

Multi-step reaction with 6 steps

1: MeONa / benzene / 18.5 h / 12 °C

2: TsN₃, triethylamine / CH₂Cl₂ / 24 h / 20 °C

3: 86 percent / triethylamine / methanol / 24 h / Irradiation

4: pyridine, pyridinium bromide perbromide / CH₂Cl₂ / 3.5 h / 0 °C

5: LiCl, Li₂CO₃, HMPA / 42 h / 40 - 100 °C

6: 1.) LDA, 2.) HMPA / 1.) THF, -78 deg C, 20 min, 2.) THF, a) -78 deg C, 20 min, b) -40 deg C, 1 h

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; 4-toluenesulfonyl azide; sodium methylate; pyridinium hydrobromide perbromide; lithium carbonate; triethylamine; lithium chloride; lithium diisopropyl amide; In methanol; dichloromethane; benzene;

upstream raw materials:

diphenyl diselenide

(1S,6R)-Tricyclo[4.2.2.0^1,6]deca-2,4,9-triene-7-carboxylic acid methyl ester

1,4-cyclohexadiene-1,2-dicarboxylic anhydride

(3aS,7aR)-3a,7a-Etheno-inden-2-one

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