(Z)-3-((dimethylamino)methylene)-4-(4-fluorophenyl)-5-phenyl-2-(trifluoromethyl)cyclopenta-1,4-dienecarbaldehyde

Base Information

• Chemical Name: (Z)-3-((dimethylamino)methylene)-4-(4-fluorophenyl)-5-phenyl-2-(trifluoromethyl)cyclopenta-1,4-dienecarbaldehyde
• CAS No.: 1459697-36-9
• Molecular Formula: C₂₂H₁₇F₄NO
• Molecular Weight: 387.377
• Mol file: 1459697-36-9.mol

Synonyms:

Chemical Property of (Z)-3-((dimethylamino)methylene)-4-(4-fluorophenyl)-5-phenyl-2-(trifluoromethyl)cyclopenta-1,4-dienecarbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-3-((dimethylamino)methylene)-4-(4-fluorophenyl)-5-phenyl-2-(trifluoromethyl)cyclopenta-1,4-dienecarbaldehyde

There total 5 articles about (Z)-3-((dimethylamino)methylene)-4-(4-fluorophenyl)-5-phenyl-2-(trifluoromethyl)cyclopenta-1,4-dienecarbaldehyde 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:

1-(4-fluorophenyl)-5-phenyl-3-(trifluoromethyl)penta-1,4-dien-3-ol + N,N-dimethyl-formamide (68-12-2,33513-42-7) → (Z)-3-((dimethylamino)methylene)-5-(4-fluorophenyl)-4-phenyl-2-(trifluoromethyl)cyclopenta-1,4-dienecarbaldehyde (1459697-32-5) + (Z)-3-((dimethylamino)methylene)-4-(4-fluorophenyl)-5-phenyl-2-(trifluoromethyl)cyclopenta-1,4-dienecarbaldehyde (1459697-36-9)

Guidance literature:

1-(4-fluorophenyl)-5-phenyl-3-(trifluoromethyl)penta-1,4-dien-3-ol; With boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; at 35 ℃;

N,N-dimethyl-formamide; With trichlorophosphate; In 1,2-dichloro-ethane; at 75 ℃; Overall yield = 86 %;

DOI:10.1039/c3ob41400k

Reference yield:

C17H13FO (368842-45-9) → (Z)-3-((dimethylamino)methylene)-5-(4-fluorophenyl)-4-phenyl-2-(trifluoromethyl)cyclopenta-1,4-dienecarbaldehyde (1459697-32-5) + (Z)-3-((dimethylamino)methylene)-4-(4-fluorophenyl)-5-phenyl-2-(trifluoromethyl)cyclopenta-1,4-dienecarbaldehyde (1459697-36-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium acetate / N,N-dimethyl-formamide / 0.33 h / 20 °C

2.1: hydrogenchloride / water; tetrahydrofuran / 20 °C

3.1: boron trifluoride diethyl etherate / 1,2-dichloro-ethane / 35 °C

3.2: 75 °C

With hydrogenchloride; boron trifluoride diethyl etherate; sodium acetate; In tetrahydrofuran; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 3.1: |Nazarov Cyclization / 3.2: |Vilsmeier Reaction;

DOI:10.1039/c3ob41400k

Reference yield:

benzaldehyde (100-52-7) → (Z)-3-((dimethylamino)methylene)-5-(4-fluorophenyl)-4-phenyl-2-(trifluoromethyl)cyclopenta-1,4-dienecarbaldehyde (1459697-32-5) + (Z)-3-((dimethylamino)methylene)-4-(4-fluorophenyl)-5-phenyl-2-(trifluoromethyl)cyclopenta-1,4-dienecarbaldehyde (1459697-36-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydroxide / ethanol / 20 °C

2.1: sodium acetate / N,N-dimethyl-formamide / 0.33 h / 20 °C

3.1: hydrogenchloride / water; tetrahydrofuran / 20 °C

4.1: boron trifluoride diethyl etherate / 1,2-dichloro-ethane / 35 °C

4.2: 75 °C

With hydrogenchloride; boron trifluoride diethyl etherate; sodium acetate; sodium hydroxide; In tetrahydrofuran; ethanol; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 4.1: |Nazarov Cyclization / 4.2: |Vilsmeier Reaction;

DOI:10.1039/c3ob41400k

upstream raw materials:

N,N-dimethyl-formamide

C₁₇H₁₃FO

benzaldehyde

4-(4-fluorophenyl)but-3-en-2-one