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

Base Information

• Chemical Name: (4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene
• CAS No.: 149404-74-0
• Molecular Formula: C₁₄H₂₀O₂
• Molecular Weight: 220.312
• Mol file: 149404-74-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene 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: 69.0%

zinc diacetate (557-34-6) + (1S,4R,5R)-4,6,6-trimethyl-4-vinylbicyclo[3.1.1]heptan-2-one (134655-24-6) → (4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene (149404-74-0)

Guidance literature:

With boron trifluoride diethyl etherate; acetic anhydride; for 72h; Ambient temperature;

DOI:10.1021/jo00067a026

Reference yield:

(1R,5S)-(+)-nopinone (38651-65-9) → (4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene (149404-74-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / SeO₂, MsOH / CH₂Cl₂ / Ambient temperature

2: 70 percent / 7.5percent H₂O₂, pyridine / CH₂Cl₂ / 1) 0 deg C, 5 h, 2) room temp., 2 h

3: diethyl ether / 0.5 h / Ambient temperature

4: 79 percent / PCC, Celite / CH₂Cl₂ / Ambient temperature

5: 85 percent / CuI / tetrahydrofuran / -50 deg C to room temp., 2 h

6: 69 percent / BF₃*OEt₂, acetic anhydride / 72 h / Ambient temperature

With pyridine; copper(l) iodide; selenium(IV) oxide; methanesulfonic acid; Celite; boron trifluoride diethyl etherate; dihydrogen peroxide; acetic anhydride; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo00067a026

Reference yield:

(-)-Verbenone (80-57-9,1196-01-6) → (4R,5R)-1-Acetoxy-4-isopropenyl-5-methyl-5-vinylcyclohex-1-ene (149404-74-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / CuI / tetrahydrofuran / -50 deg C to room temp., 2 h

2: 69 percent / BF₃*OEt₂, acetic anhydride / 72 h / Ambient temperature

With copper(l) iodide; boron trifluoride diethyl etherate; acetic anhydride; In tetrahydrofuran;

DOI:10.1021/jo00067a026

upstream raw materials:

zinc diacetate

(1S,4R,5R)-4,6,6-trimethyl-4-vinylbicyclo[3.1.1]heptan-2-one

(1R,5S)-(+)-nopinone

(-)-Verbenone

Downstream raw materials:

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

(1R,2S,4R,5R)-2-Hydroxy-5-isopropenyl-4-methyl-4-vinyl-cyclohexanecarboxylic acid ethyl ester

(4R,5R)-5-Isopropenyl-4-methyl-4-vinyl-cyclohex-1-enecarboxylic acid ethyl ester

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