1-diazo-3,3-dimethyl-5-phenylhex-5-en-2-one

Base Information

• Chemical Name: 1-diazo-3,3-dimethyl-5-phenylhex-5-en-2-one
• CAS No.: 1447969-34-7
• Molecular Formula: C₁₄H₁₆N₂O
• Molecular Weight: 228.294
• Mol file: 1447969-34-7.mol

Synonyms:

Chemical Property of 1-diazo-3,3-dimethyl-5-phenylhex-5-en-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-diazo-3,3-dimethyl-5-phenylhex-5-en-2-one

There total 4 articles about 1-diazo-3,3-dimethyl-5-phenylhex-5-en-2-one 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:

3-bromo-2-phenylprop-1-ene (3360-54-1) → 1-diazo-3,3-dimethyl-5-phenylhex-5-en-2-one (1447969-34-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; ethylbenzene; n-heptane / 2.5 h / -78 - -40 °C / Schlenk technique; Inert atmosphere

1.2: 20 °C / Schlenk technique; Inert atmosphere

2.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 48 h / 20 °C

3.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 4 h / 0 °C / Inert atmosphere; Schlenk technique

4.1: dichloromethane / 2 h / 20 °C / Inert atmosphere

4.3: 15 h / 20 °C / Schlenk technique; Inert atmosphere

With oxalyl dichloride; lithium hydroxide monohydrate; lithium diisopropyl amide; In tetrahydrofuran; methanol; n-heptane; dichloromethane; ethylbenzene; water; N,N-dimethyl-formamide;

DOI:10.1021/ja404394z

Reference yield:

isopropenylbenzene (98-83-9,6144-04-3,25014-31-7,42612-14-6) → 1-diazo-3,3-dimethyl-5-phenylhex-5-en-2-one (1447969-34-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: N-Bromosuccinimide; tetrachloromethane / 0.25 h / Reflux; Inert atmosphere

2.1: lithium diisopropyl amide / tetrahydrofuran; ethylbenzene; n-heptane / 2.5 h / -78 - -40 °C / Schlenk technique; Inert atmosphere

2.2: 20 °C / Schlenk technique; Inert atmosphere

3.1: lithium hydroxide monohydrate / tetrahydrofuran; methanol; water / 48 h / 20 °C

4.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 4 h / 0 °C / Inert atmosphere; Schlenk technique

5.1: dichloromethane / 2 h / 20 °C / Inert atmosphere

5.3: 15 h / 20 °C / Schlenk technique; Inert atmosphere

With tetrachloromethane; N-Bromosuccinimide; oxalyl dichloride; lithium hydroxide monohydrate; lithium diisopropyl amide; In tetrahydrofuran; methanol; n-heptane; dichloromethane; ethylbenzene; water; N,N-dimethyl-formamide;

DOI:10.1021/ja404394z

Reference yield:

2,2-dimethyl-4-phenylpent-4-enoic acid (1258203-89-2) → 1-diazo-3,3-dimethyl-5-phenylhex-5-en-2-one (1447969-34-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: oxalyl dichloride / dichloromethane; N,N-dimethyl-formamide / 4 h / 0 °C / Inert atmosphere; Schlenk technique

2.1: dichloromethane / 2 h / 20 °C / Inert atmosphere

2.3: 15 h / 20 °C / Schlenk technique; Inert atmosphere

With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja404394z

upstream raw materials:

methyl 2,2-dimethyl-4-phenylpent-4-enoate

3-bromo-2-phenylprop-1-ene

isopropenylbenzene

2,2-dimethyl-4-phenylpent-4-enoic acid

Downstream raw materials:

3,3-dimethyl-5-phenylbicyclo[3.1.0]hexan-2-one

3,3-dimethyl-2,3-dihydro-[1,1'-biphenyl]-4(1H)-one