C₁₄H₁₉NO

Base Information

• Chemical Name: C₁₄H₁₉NO
• CAS No.: 1338724-16-5
• Molecular Formula: C₁₄H₁₉NO
• Molecular Weight: 217.311
• Mol file: 1338724-16-5.mol

Synonyms:C₁₄H₁₉NO

Chemical Property of C₁₄H₁₉NO

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₁₄H₁₉NO

There total 1 articles about C₁₄H₁₉NO 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: 66.0%

bromopropionitrile (2417-90-5) + (R)-6-methylcarvone (138812-34-7) → C14H19NO (1338724-16-5)

Guidance literature:

(R)-6-methylcarvone; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 5h; Inert atmosphere;

bromopropionitrile; In tetrahydrofuran; at -78 ℃; for 16h; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2011.06.084

Reference yield: 97.0%

C14H19NO (1338724-16-5) → C14H19NO2 (1338724-15-4)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tet.2011.06.084

Reference yield:

C14H19NO (1338724-16-5) → α-pyronemeroterpenoid pyripyropene A (147444-03-9)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2.1: bis(cyclopentadienyl)titanium dichloride; zinc / tetrahydrofuran / 0.75 h / 20 °C / Inert atmosphere

3.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 0.5 h / -40 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: acetic acid; N-bromoacetamide / 6.5 h / 20 °C / Inert atmosphere

5.1: potassium carbonate / methanol / 7 h / 20 °C / Inert atmosphere

6.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

7.1: sec.-butyllithium / tetrahydrofuran / 0.5 h / -23 °C / Inert atmosphere

7.2: 0.5 h / -78 - -60 °C / Inert atmosphere

8.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 1 h / 50 °C / Inert atmosphere

9.1: isopropylmagnesium chloride / 0.5 h / -30 °C / Inert atmosphere

9.2: -30 - 20 °C / Inert atmosphere

9.3: Inert atmosphere

10.1: Dess-Martin periodane / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

11.1: toluene / 5 h / 80 °C / Inert atmosphere

12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 8 h / 100 °C / Inert atmosphere

13.1: lithium hexamethyldisilazane / tetrahydrofuran / 4 h / 0 - 20 °C / Inert atmosphere

13.2: 2 h / 20 °C / Inert atmosphere

14.1: methanol; acetyl chloride / 1 h / 20 °C / Inert atmosphere

14.2: 0.5 h / 20 °C / Inert atmosphere

15.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.5 h / -78 °C / Inert atmosphere

With 1H-imidazole; 2,6-dimethylpyridine; methanol; dmap; bis(cyclopentadienyl)titanium dichloride; sodium tetrahydroborate; cerium(III) chloride heptahydrate; sec.-butyllithium; isopropylmagnesium chloride; potassium carbonate; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; acetyl chloride; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride; zinc; N-bromoacetamide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 3.1: Evans reduction / 7.2: Peterson olefination / 10.1: Dess-Martin oxidation / 12.1: hetero-Michael addition / 15.1: Luche reduction;

DOI:10.1016/j.tet.2011.06.084

upstream raw materials:

bromopropionitrile

(R)-6-methylcarvone

Downstream raw materials:

C₁₄H₁₉NO₂

α-pyronemeroterpenoid pyripyropene A