(S)-3-(2-[1,3]Dioxolan-2-yl-ethyl)-5-isopropenyl-2-methyl-cyclohex-2-enone

Base Information

• Chemical Name: (S)-3-(2-[1,3]Dioxolan-2-yl-ethyl)-5-isopropenyl-2-methyl-cyclohex-2-enone
• CAS No.: 853562-37-5
• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.338
• Mol file: 853562-37-5.mol

Synonyms:(S)-3-(2-[1,3]Dioxolan-2-yl-ethyl)-5-isopropenyl-2-methyl-cyclohex-2-enone

Chemical Property of (S)-3-(2-[1,3]Dioxolan-2-yl-ethyl)-5-isopropenyl-2-methyl-cyclohex-2-enone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-(2-[1,3]Dioxolan-2-yl-ethyl)-5-isopropenyl-2-methyl-cyclohex-2-enone

There total 1 articles about (S)-3-(2-[1,3]Dioxolan-2-yl-ethyl)-5-isopropenyl-2-methyl-cyclohex-2-enone 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: 80.0%

2-bromo-2-(2-ethyl)dioxolane (18742-02-4) + (R)-Carvone (6485-40-1,2244-16-8) → (S)-3-(2-[1,3]Dioxolan-2-yl-ethyl)-5-isopropenyl-2-methyl-cyclohex-2-enone (853562-37-5)

Guidance literature:

2-bromo-2-(2-ethyl)dioxolane; (R)-Carvone; With lithium; In tetrahydrofuran; for 1h;

With silica gel; pyridinium chlorochromate; In dichloromethane; for 4h;

DOI:10.1016/j.tetlet.2005.03.088

Reference yield: 85.0%

(S)-3-(2-[1,3]Dioxolan-2-yl-ethyl)-5-isopropenyl-2-methyl-cyclohex-2-enone (853562-37-5) + methyl iodide (74-88-4) → (3R,5S)-3-(2-[1,3]Dioxolan-2-yl-ethyl)-5-isopropenyl-2,2-dimethyl-cyclohexanone (853562-38-6)

Guidance literature:

With ammonia; lithium; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2005.03.088

Reference yield:

(S)-3-(2-[1,3]Dioxolan-2-yl-ethyl)-5-isopropenyl-2-methyl-cyclohex-2-enone (853562-37-5) → (R)-5-(2-[1,3]Dioxolan-2-yl-ethyl)-2,6,6-trimethyl-cyclohex-2-enone (853562-40-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 85 percent / Li; liq. NH₃ / tetrahydrofuran

2.1: 85 percent / LDA / tetrahydrofuran / 15 h / -70 - 20 °C

3.1: O₃; O₂ / methanol; CH₂Cl₂ / -70 °C

3.2: 70 percent / Ac₂O; Et₃N; DMAP / benzene / 6 h / Heating

With ammonia; oxygen; lithium; ozone; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; 3.1: Criegee fragmentation;

DOI:10.1016/j.tetlet.2005.03.088

upstream raw materials:

2-bromo-2-(2-ethyl)dioxolane

(R)-Carvone

Downstream raw materials:

(3R,5S)-3-(2-[1,3]Dioxolan-2-yl-ethyl)-5-isopropenyl-2,2-dimethyl-cyclohexanone

(R)-5-(2-[1,3]Dioxolan-2-yl-ethyl)-2,6,6-trimethyl-cyclohex-2-enone

(1S,5R)-1-Allyl-5-but-3-enyl-2,6,6-trimethyl-cyclohex-2-enol

(3R,5S)-3-(2-[1,3]Dioxolan-2-yl-ethyl)-5-isopropenyl-2,2,6-trimethyl-cyclohexanone