(1R,2R,5R,6R,8R,9R)-4'-bromo-2-(2-propenyl)-5,9-dimethyl-7-oxa-8-bicyclo<4.3.0>nonanemethanilide

Base Information

Chemical Name:(1R,2R,5R,6R,8R,9R)-4'-bromo-2-(2-propenyl)-5,9-dimethyl-7-oxa-8-bicyclo<4.3.0>nonanemethanilide
CAS No.:108510-46-9
Molecular Formula:C₂₀H₂₆BrNO₂
Molecular Weight:392.336
Hs Code.:

Synonyms:(1R,2R,5R,6R,8R,9R)-4'-bromo-2-(2-propenyl)-5,9-dimethyl-7-oxa-8-bicyclo<4.3.0>nonanemethanilide

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Chemical Property of (1R,2R,5R,6R,8R,9R)-4'-bromo-2-(2-propenyl)-5,9-dimethyl-7-oxa-8-bicyclo<4.3.0>nonanemethanilide

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Technology Process of (1R,2R,5R,6R,8R,9R)-4'-bromo-2-(2-propenyl)-5,9-dimethyl-7-oxa-8-bicyclo<4.3.0>nonanemethanilide

There total 7 articles about (1R,2R,5R,6R,8R,9R)-4'-bromo-2-(2-propenyl)-5,9-dimethyl-7-oxa-8-bicyclo<4.3.0>nonanemethanilide 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: 74.0%

: 108510-49-2
(1R,2R,5R,6R,8R,9R)-2-(2-propenyl)-5,9-dimethyl-8-carboxy-7-oxabicyclo<4.3.0>nonane

: 106-40-1
4-bromo-aniline

: 108510-46-9
(1R,2R,5R,6R,8R,9R)-4'-bromo-2-(2-propenyl)-5,9-dimethyl-7-oxa-8-bicyclo<4.3.0>nonanemethanilide

Guidance literature:: With 1,1'-carbonyldiimidazole; In dichloromethane; at 21 ℃; for 14h;
DOI:10.1021/jo00389a022

Reference yield:

: 6485-40-1,2244-16-8
(R)-Carvone

: 108510-46-9
(1R,2R,5R,6R,8R,9R)-4'-bromo-2-(2-propenyl)-5,9-dimethyl-7-oxa-8-bicyclo<4.3.0>nonanemethanilide

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) LDA / 1.) THF, hexane, -78 deg C, 10 min, 2.) THF, hexane, -78 deg, 1h,

2: MeSO₂Cl,Et₃N / CH₂Cl₂ / 0.58 h / 0 °C

3: K-Selectride / tetrahydrofuran / 1.42 h / -78 °C

4: L-Selectride / tetrahydrofuran / 1 h / -78 °C

5: 98 percent / NaH / tetrahydrofuran; ethanol / 17 h / Heating

6: 1.) LDA, 2.) HMPT / 1.) THF, hexane, 0 deg C, 3 min, 2.) THF, hexane, a.) 185 deg C, 45 min, b.) RT, 14 h

7: 74 percent / carbonyldiimidazole / CH₂Cl₂ / 14 h / 21 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; L-Selectride; sodium hydride; potassium tri-sec-butyl-borohydride; methanesulfonyl chloride; triethylamine; 1,1'-carbonyldiimidazole; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/jo00389a022

Reference yield:

: 108510-47-0
(5R,6S)-2-methyl-5-(2-propenyl)-6-ethenyl-2-cyclohexenone

: 108510-46-9
(1R,2R,5R,6R,8R,9R)-4'-bromo-2-(2-propenyl)-5,9-dimethyl-7-oxa-8-bicyclo<4.3.0>nonanemethanilide

Guidance literature:: Multi-step reaction with 5 steps

1: K-Selectride / tetrahydrofuran / 1.42 h / -78 °C

2: L-Selectride / tetrahydrofuran / 1 h / -78 °C

3: 98 percent / NaH / tetrahydrofuran; ethanol / 17 h / Heating

4: 1.) LDA, 2.) HMPT / 1.) THF, hexane, 0 deg C, 3 min, 2.) THF, hexane, a.) 185 deg C, 45 min, b.) RT, 14 h

5: 74 percent / carbonyldiimidazole / CH₂Cl₂ / 14 h / 21 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; L-Selectride; sodium hydride; potassium tri-sec-butyl-borohydride; 1,1'-carbonyldiimidazole; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane;
DOI:10.1021/jo00389a022