(1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)-1-vinylcyclohexanol

Base Information

• Chemical Name: (1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)-1-vinylcyclohexanol
• CAS No.: 1277192-52-5
• Molecular Formula: C₁₂H₂₀O
• Molecular Weight: 180.29
• Mol file: 1277192-52-5.mol

Synonyms:(1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)-1-vinylcyclohexanol

Chemical Property of (1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)-1-vinylcyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)-1-vinylcyclohexanol

There total 1 articles about (1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)-1-vinylcyclohexanol 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: 92.0%

(?)-trans-isopulegone (17882-43-8) + vinyl magnesium bromide (1826-67-1) → (1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)-1-vinylcyclohexanol (1277192-52-5)

Guidance literature:

In tetrahydrofuran; at -80 - 20 ℃;

DOI:10.1021/ol200499t

Reference yield:

(1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)-1-vinylcyclohexanol (1277192-52-5) → (1R,3aR,4R,7R,8S,8aR)-7-isopropyl-1,4-dimethyldecahydro-4,7-epoxyazulen-8-yl cinnamate

Guidance literature:

Multi-step reaction with 11 steps

1.1: 18-crown-6 ether; potassium hydride / tetrahydrofuran / 12 h / Reflux

2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 20 °C

3.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / Reflux

3.2: 12 h / -10 - 0 °C

4.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -45 °C

4.2: -78 °C

5.1: Burgess Reagent / toluene / 0.08 h / 110 °C

6.1: methanol; potassium carbonate / 4 h / 70 °C

7.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / -10 - 20 °C

8.1: mercury(II) trifluoroacetate / methanol; dichloromethane / 12 h / -78 °C

8.2: 3 h / -78 - 20 °C

9.1: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C

10.1: triethylsilane; titanium tetrachloride / dichloromethane / 0.5 h / -78 °C

11.1: dmap; 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 12 h / 20 °C

With methanol; triethylsilane; dmap; lithium aluminium tetrahydride; Burgess Reagent; 18-crown-6 ether; 2,4,6-trichlorobenzoyl chloride; mercury(II) trifluoroacetate; titanium tetrachloride; potassium hydride; sodium hydride; potassium carbonate; Dess-Martin periodane; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; toluene; mineral oil; 1.1: oxy-Cope rearrangement;

DOI:10.1021/ol200499t

upstream raw materials:

(?)-trans-isopulegone

vinyl magnesium bromide

Refernces