(1R,5R,6R)-6-Methyl-2-methylene-6-(3-oxo-propyl)-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester

Base Information

Chemical Name:(1R,5R,6R)-6-Methyl-2-methylene-6-(3-oxo-propyl)-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester
CAS No.:122346-56-9
Molecular Formula:C₁₃H₁₈O₃
Molecular Weight:222.284
Hs Code.:

Synonyms:(1R,5R,6R)-6-Methyl-2-methylene-6-(3-oxo-propyl)-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester

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Chemical Property of (1R,5R,6R)-6-Methyl-2-methylene-6-(3-oxo-propyl)-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester

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Technology Process of (1R,5R,6R)-6-Methyl-2-methylene-6-(3-oxo-propyl)-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester

There total 1 articles about (1R,5R,6R)-6-Methyl-2-methylene-6-(3-oxo-propyl)-bicyclo[3.1.0]hexane-1-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:

: 5389-87-7
1-chloro-3,7-dimethylocta-2,6-diene

: 122346-56-9
(1R,5R,6R)-6-Methyl-2-methylene-6-(3-oxo-propyl)-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) NaH, n-BuLi / 1.) THF, 0 deg C, 2.) from -30 deg C to room temperature

2: tosyl azide, triethyl amine / acetonitrile / Ambient temperature

3: copper powder / CH₂Cl₂ / Heating

4: 80 percent / m-choloroperbenzoic acid, potassium carbonate / CH₂Cl₂ / -50 °C

5: periodic acid / diethyl ether / 0 °C

With n-butyllithium; 4-toluenesulfonyl azide; copper; sodium hydride; potassium carbonate; periodic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In diethyl ether; dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(00)80710-8

Reference yield:

: 122346-56-9
(1R,5R,6R)-6-Methyl-2-methylene-6-(3-oxo-propyl)-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester

: 122346-60-5
Acetic acid (3aS,3bS,7aS)-6-benzenesulfonyl-1,3b-dimethyl-3a,3b,4,5,6,7-hexahydro-3H-cyclopenta[1,3]cyclopropa[1,2]benzen-7-yl ester

Guidance literature:: Multi-step reaction with 7 steps

1: sodium borohydride / methanol / 0 °C

2: triethyl amine / DMAP / CH₂Cl₂ / Ambient temperature

3: sodium iodide / acetone / Heating

4: dimethylformamide / Ambient temperature

5: lithium diisopropylamine / tetrahydrofuran / 0.17 h / -78 °C

6: sodium borohydride / diethyl ether; methanol / from -50 deg C to 0 deg C

7: Et₃N / DMAP / CH₂Cl₂ / Ambient temperature

With sodium tetrahydroborate; triethylamine; sodium iodide; lithium diisopropyl amide; dmap; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4039(00)80710-8

Reference yield:

: 122346-56-9
(1R,5R,6R)-6-Methyl-2-methylene-6-(3-oxo-propyl)-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester

: 122346-58-1
(1R,5R,6R)-6-Methyl-2-methylene-6-[3-(toluene-4-sulfonyloxy)-propyl]-bicyclo[3.1.0]hexane-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: sodium borohydride / methanol / 0 °C

2: triethyl amine / DMAP / CH₂Cl₂ / Ambient temperature

With sodium tetrahydroborate; triethylamine; dmap; In methanol; dichloromethane;
DOI:10.1016/S0040-4039(00)80710-8