(S,E)-1-(prop-1'-en-1'-yl)-4-phenyl-N⁽⁵⁾-methyl-1,5-diazocan-2-one

Base Information

• Chemical Name: (S,E)-1-(prop-1'-en-1'-yl)-4-phenyl-N⁽⁵⁾-methyl-1,5-diazocan-2-one
• CAS No.: 1393593-69-5
• Molecular Formula: C₁₆H₂₂N₂O
• Molecular Weight: 258.363
• Mol file: 1393593-69-5.mol

Synonyms:

Chemical Property of (S,E)-1-(prop-1'-en-1'-yl)-4-phenyl-N⁽⁵⁾-methyl-1,5-diazocan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S,E)-1-(prop-1'-en-1'-yl)-4-phenyl-N⁽⁵⁾-methyl-1,5-diazocan-2-one

There total 18 articles about (S,E)-1-(prop-1'-en-1'-yl)-4-phenyl-N⁽⁵⁾-methyl-1,5-diazocan-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: 42.0%

(S)-N(1)-allyl-4-phenyl-N(5)-methyl-1,5-diazocan-2-one (1393593-64-0) → (S,E)-1-(prop-1'-en-1'-yl)-4-phenyl-N(5)-methyl-1,5-diazocan-2-one (1393593-69-5) + (S,E)-1,4-di[2'-oxo-4'-phenyl-N(5')-methyl-1',5'-diazocan-1'-yl]but-2-ene (1393593-66-2)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 40 ℃; for 16h;

DOI:10.1021/jo3012732

Reference yield:

methyl (3S,αR)-3-[N-( 3'-chloropropyl)-N-(α-methyl-4''-methoxybenzyl)amino]-3-phenylpropanoate (1356849-80-3) → (S,E)-1-(prop-1'-en-1'-yl)-4-phenyl-N(5)-methyl-1,5-diazocan-2-one (1393593-69-5) + (S,E)-1,4-di[2'-oxo-4'-phenyl-N(5')-methyl-1',5'-diazocan-1'-yl]but-2-ene (1393593-66-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium azide; sodium iodide / dimethyl sulfoxide / 24 h / 50 °C

2.1: triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C

2.2: 2 h / 50 °C

3.1: triethoxyantimony / toluene / 2 h / Molecular sieve; Reflux

4.1: formic acid / 2.5 h / Reflux

5.1: N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; sodium hydroxide / tetrahydrofuran / 18 h / 75 °C

6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 16 h / 40 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium azide; triethoxyantimony; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; triphenylphosphine; sodium iodide; sodium hydroxide; In tetrahydrofuran; formic acid; dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1021/jo3012732

Reference yield:

methyl (3S, αR)-3-[N-( 3'-chloropropyl)-N-(α-methylbenzyl)amino]-3-phenylpropanoate (1393593-35-5) → (S,E)-1-(prop-1'-en-1'-yl)-4-phenyl-N(5)-methyl-1,5-diazocan-2-one (1393593-69-5) + (S,E)-1,4-di[2'-oxo-4'-phenyl-N(5')-methyl-1',5'-diazocan-1'-yl]but-2-ene (1393593-66-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium azide; sodium iodide / dimethyl sulfoxide / 24 h / 50 °C

2.1: triphenylphosphine / tetrahydrofuran / 0.5 h / 20 °C

2.2: 2 h / 50 °C

3.1: triethoxyantimony / toluene / 2 h / Molecular sieve; Reflux

4.1: 20 % Pd(OH)2/C; hydrogen; acetic acid / methanol / 72 h / 20 °C / 3800.26 Torr

5.1: N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; sodium hydroxide / tetrahydrofuran / 18 h / 75 °C

6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 16 h / 40 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium azide; 20 % Pd(OH)2/C; triethoxyantimony; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; potassium carbonate; acetic acid; triphenylphosphine; sodium iodide; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1021/jo3012732

upstream raw materials:

methyl (S)-3-[N-(3'-chloropropyl)-N-methylamino]-3-phenylpropanoate

methyl (S)-3-[N-(3'-azidopropyl)-N-methylamino]-3-phenylpropanoate

C₁₄H₂₂N₂O₂

(R)-N-(3-chloroprop-1-yl)-N-(α-methyl-4'-methoxybenzyl)amine