2-((1S,4R,5R)-5-Isopropenyl-4-methyl-4-vinylcyclohex-1-yl)but-3-en-2-ol

Base Information

• Chemical Name: 2-((1S,4R,5R)-5-Isopropenyl-4-methyl-4-vinylcyclohex-1-yl)but-3-en-2-ol
• CAS No.: 202194-35-2
• Molecular Formula: C₁₆H₂₆O
• Molecular Weight: 234.382
• Mol file: 202194-35-2.mol

Synonyms:2-((1S,4R,5R)-5-Isopropenyl-4-methyl-4-vinylcyclohex-1-yl)but-3-en-2-ol

Chemical Property of 2-((1S,4R,5R)-5-Isopropenyl-4-methyl-4-vinylcyclohex-1-yl)but-3-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((1S,4R,5R)-5-Isopropenyl-4-methyl-4-vinylcyclohex-1-yl)but-3-en-2-ol

There total 8 articles about 2-((1S,4R,5R)-5-Isopropenyl-4-methyl-4-vinylcyclohex-1-yl)but-3-en-2-ol 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: 97.0%

(1S,3R,4R)-1-Acetyl-3-isopropenyl-4-methyl-4-vinylcyclohexane (70224-50-9) + vinyl magnesium bromide (1826-67-1) → 2-((1S,4R,5R)-5-Isopropenyl-4-methyl-4-vinylcyclohex-1-yl)but-3-en-2-ol (202194-35-2)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 1.5h;

Reference yield:

(4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene (149404-74-0) → 2-((1S,4R,5R)-5-Isopropenyl-4-methyl-4-vinylcyclohex-1-yl)but-3-en-2-ol (202194-35-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 99 percent / MeLi, HMPA / diethyl ether; tetrahydrofuran / 1.) -78 deg C, 1 h, 2.) -78 deg C, 35 min

2: 71 percent / NaBH₄ / ethanol / 13 h / 0 - 20 °C

3: Et₃N / diethyl ether / 3 h / 0 °C

4: DBU / diethyl ether / 4 h

5: 3 M aq. KOH / ethanol / 1 h / Heating

6: tetrahydrofuran; diethyl ether / 0.67 h / 0 °C

7: CuI, LiAlH₄ / tetrahydrofuran / 1 h

8: 97 percent / tetrahydrofuran / 1.5 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium tetrahydroborate; copper(l) iodide; lithium aluminium tetrahydride; methyllithium; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; diethyl ether; ethanol;

Reference yield:

(4R,5R)-5-Isopropenyl-4-methyl-4-vinylcyclohexen-1-yl methyl ketone (202194-31-8) → 2-((1S,4R,5R)-5-Isopropenyl-4-methyl-4-vinylcyclohex-1-yl)but-3-en-2-ol (202194-35-2)

Guidance literature:

Multi-step reaction with 2 steps

1: CuI, LiAlH₄ / tetrahydrofuran / 1 h

2: 97 percent / tetrahydrofuran / 1.5 h / 0 °C

With copper(l) iodide; lithium aluminium tetrahydride; In tetrahydrofuran;

upstream raw materials:

(1S,3R,4R)-1-Acetyl-3-isopropenyl-4-methyl-4-vinylcyclohexane

vinyl magnesium bromide

(4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene

(4R,5R)-5-Isopropenyl-4-methyl-4-vinylcyclohexen-1-yl methyl ketone

Downstream raw materials:

(E)-3-((1S,4R,5R)-5-Isopropenyl-4-methyl-4-vinylcyclohex-1-yl)but-2-enal

(2E,4E)-5-((1S,3R,4R)-3-Isopropenyl-4-methyl-4-vinyl-cyclohexyl)-hexa-2,4-dienoic acid methyl ester