(1R,3S,5S)-3-Hydroxy-2-methylene-bicyclo[3.1.0]hexane-1-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Base Information

Chemical Name:(1R,3S,5S)-3-Hydroxy-2-methylene-bicyclo[3.1.0]hexane-1-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
CAS No.:101046-89-3
Molecular Formula:C₁₈H₂₈O₃
Molecular Weight:292.419
Hs Code.:

Synonyms:(1R,3S,5S)-3-Hydroxy-2-methylene-bicyclo[3.1.0]hexane-1-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

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Chemical Property of (1R,3S,5S)-3-Hydroxy-2-methylene-bicyclo[3.1.0]hexane-1-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

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Technology Process of (1R,3S,5S)-3-Hydroxy-2-methylene-bicyclo[3.1.0]hexane-1-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

There total 5 articles about (1R,3S,5S)-3-Hydroxy-2-methylene-bicyclo[3.1.0]hexane-1-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl 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: 29.0%

: 93489-96-4
(-)-menthyl (1R,5R)-2-methylenebicyclo<3.1.0>hexane-1-carboxylate

: 101046-89-3
(1R,3S,5S)-3-Hydroxy-2-methylene-bicyclo[3.1.0]hexane-1-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

: 111594-57-1
(1R,5S)-2-Methylene-3-oxo-bicyclo[3.1.0]hexane-1-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Guidance literature:: With tert.-butylhydroperoxide; selenium(IV) oxide; In dichloromethane; for 1h;

Reference yield:

: 74985-54-9
(-)-menthyl (1R,5R)-2-oxobicyclo<3.1.0>hexane-1-carboxylate

: 101046-89-3
(1R,3S,5S)-3-Hydroxy-2-methylene-bicyclo[3.1.0]hexane-1-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) sodium 2-methylbutan-2-olate / 1.) toluene, 0 deg C; room temperature, 2 h, 2.) toluene, room temperature, 2 h

2: 37 percent / selenium dioxide, t-butylhydroperoxide / CH₂Cl₂ / 1 h

With tert.-butylhydroperoxide; selenium(IV) oxide; sodium tert-pentoxide; In dichloromethane;

Reference yield:

: 2216-51-5
(-)-menthol

: 101046-89-3
(1R,3S,5S)-3-Hydroxy-2-methylene-bicyclo[3.1.0]hexane-1-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 50 percent / 4-(dimethylamino)pyridine (DMAP), dicyclohexylcarbodi-imide (DCC) / CH₂Cl₂ / 1.) 0 deg C, 2.) room temperature, 2.5 h

2: 1.) sodium 2-methylbutan-2-olate / 1.) toluene, 0 deg C; room temperature, 2 h, 2.) toluene, room temperature, 2 h

3: 37 percent / selenium dioxide, t-butylhydroperoxide / CH₂Cl₂ / 1 h

With tert.-butylhydroperoxide; dmap; selenium(IV) oxide; sodium tert-pentoxide; dicyclohexyl-carbodiimide; In dichloromethane;