(R)-N-(bis(3,5-dimethylphenyl)methylene)-1-(4-methoxyphenyl)but-3-en-1-amine

Base Information

• Chemical Name: (R)-N-(bis(3,5-dimethylphenyl)methylene)-1-(4-methoxyphenyl)but-3-en-1-amine
• CAS No.: 1285695-81-9
• Molecular Formula: C₂₈H₃₁NO
• Molecular Weight: 397.56
• Mol file: 1285695-81-9.mol

Synonyms:(R)-N-(bis(3,5-dimethylphenyl)methylene)-1-(4-methoxyphenyl)but-3-en-1-amine

Chemical Property of (R)-N-(bis(3,5-dimethylphenyl)methylene)-1-(4-methoxyphenyl)but-3-en-1-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-N-(bis(3,5-dimethylphenyl)methylene)-1-(4-methoxyphenyl)but-3-en-1-amine

There total 6 articles about (R)-N-(bis(3,5-dimethylphenyl)methylene)-1-(4-methoxyphenyl)but-3-en-1-amine 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:

3,3’,5,5’-tetramethylbenzophenone (22679-40-9) → (R)-N-(bis(3,5-dimethylphenyl)methylene)-1-(4-methoxyphenyl)but-3-en-1-amine (1285695-81-9) + (S)-N-(bis(3,5-dimethylphenyl)methylene)-1-(4-methoxyphenyl)but-3-en-1-amine (1285695-80-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ammonia; titanium tetrachloride / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux

1.2: 0 - 20 °C / Inert atmosphere

1.3: Inert atmosphere; Cooling with ice

2.1: Mesitol; dimethylsulfide borane complex; (2S)-(-)-3,3'-diphenyl-(2,2'-binaphthalene)-1,1'-diol / m-xylene / 0.5 h / 60 °C / Inert atmosphere; Molecular sieve

2.2: 18 h / 60 °C / Inert atmosphere

With Mesitol; dimethylsulfide borane complex; ammonia; titanium tetrachloride; (2S)-(-)-3,3'-diphenyl-(2,2'-binaphthalene)-1,1'-diol; In tetrahydrofuran; m-xylene;

DOI:10.1021/ja1110865

Reference yield:

1,1-bis(3,5-dimethylphenyl)but-3-en-1-amine (1285695-66-0) + 4-methoxy-benzaldehyde (123-11-5) → (R)-N-(bis(3,5-dimethylphenyl)methylene)-1-(4-methoxyphenyl)but-3-en-1-amine (1285695-81-9) + (S)-N-(bis(3,5-dimethylphenyl)methylene)-1-(4-methoxyphenyl)but-3-en-1-amine (1285695-80-8)

Guidance literature:

1,1-bis(3,5-dimethylphenyl)but-3-en-1-amine; With Mesitol; (2R)-(+)-3,3'-diphenyl-[2,2'-dinaphthalene]-1,1'-diol; dimethylsulfide borane complex; In m-xylene; at 60 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

4-methoxy-benzaldehyde; With benzoic acid; In m-xylene; at 60 ℃; for 18h; optical yield given as %ee; Inert atmosphere;

DOI:10.1021/ja1110865

Reference yield:

5-bromo-1,3-xylene (556-96-7) → (R)-N-(bis(3,5-dimethylphenyl)methylene)-1-(4-methoxyphenyl)but-3-en-1-amine (1285695-81-9) + (S)-N-(bis(3,5-dimethylphenyl)methylene)-1-(4-methoxyphenyl)but-3-en-1-amine (1285695-80-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: iodine; magnesium / tetrahydrofuran / 8 h / Inert atmosphere; Reflux

1.2: 8 h / Inert atmosphere; Reflux

2.1: Mesitol; dimethylsulfide borane complex; (2S)-(-)-3,3'-diphenyl-(2,2'-binaphthalene)-1,1'-diol / m-xylene / 0.5 h / 60 °C / Inert atmosphere; Molecular sieve

2.2: 18 h / 60 °C / Inert atmosphere

With Mesitol; dimethylsulfide borane complex; iodine; magnesium; (2S)-(-)-3,3'-diphenyl-(2,2'-binaphthalene)-1,1'-diol; In tetrahydrofuran; m-xylene;

DOI:10.1021/ja1110865

upstream raw materials:

(R)-N-(bis(3,5-dimethylphenyl)methylene)hept-1-en-4-amine

1,1-bis(3,5-dimethylphenyl)but-3-en-1-amine

4-methoxy-benzaldehyde

5-bromo-1,3-xylene