(5E,7E,9E)-4,11-dihydroxy-13-(4-methoxyphenyl)-1-pyrrolidin-1-yltrideca-5,7,9-trien-1-one

Base Information

• Chemical Name: (5E,7E,9E)-4,11-dihydroxy-13-(4-methoxyphenyl)-1-pyrrolidin-1-yltrideca-5,7,9-trien-1-one
• CAS No.: 104227-11-4
• Molecular Formula: C₂₄H₃₃NO₄
• Molecular Weight: 399.53
• Nikkaji Number: J528.433C
• Mol file: 104227-11-4.mol

Synonyms:SM 9064;SM-9064

Chemical Property of (5E,7E,9E)-4,11-dihydroxy-13-(4-methoxyphenyl)-1-pyrrolidin-1-yltrideca-5,7,9-trien-1-one

Chemical Property:

• Vapor Pressure: 1.41E-16mmHg at 25°C
• Boiling Point: 626.9°Cat760mmHg
• Flash Point: 332.9°C
• Density: 1.128g/cm³
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 399.24095853
• Heavy Atom Count: 29
• Complexity: 543

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)CCC(C=CC=CC=CC(CCC(=O)N2CCCC2)O)O
• Isomeric SMILES: COC1=CC=C(C=C1)CCC(/C=C/C=C/C=C/C(CCC(=O)N2CCCC2)O)O

Technology Process of (5E,7E,9E)-4,11-dihydroxy-13-(4-methoxyphenyl)-1-pyrrolidin-1-yltrideca-5,7,9-trien-1-one

There total 6 articles about (5E,7E,9E)-4,11-dihydroxy-13-(4-methoxyphenyl)-1-pyrrolidin-1-yltrideca-5,7,9-trien-1-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: 44.0%

pyrrolidine (123-75-1) + methyl (5E,7E,9E)-4,11-dihydroxy-13-(p-methoxyphenyl)-trideca-5,7,9-trienoate → (5E,7E,9E)-N,N-tetramethylene-4,11-dihydroxy-13-(p-methoxyphenyl)-trideca-5,7,9-trienamide (104227-11-4)

Guidance literature:

In methanol; for 2h; Ambient temperature;

DOI:10.1080/00397919308009765

Reference yield:

pyrrolidine (123-75-1) + methyl (5E,7E,9E)-4,11-dioxo-13-(p-methoxyphenyl)-trideca-5,7,9-trienoate (104226-72-4) → (5E,7Z,9E)-N,N-tetramethylene-4,11-dihydroxy-13-(p-methoxyphenyl)-trideca-5,7,9-trienamide (104227-11-4)

Guidance literature:

With sodium borohydrid; In methanol;

Reference yield:

3-(4-methoxyphenyl)propionyl chloride (15893-42-2) → (5E,7E,9E)-N,N-tetramethylene-4,11-dihydroxy-13-(p-methoxyphenyl)-trideca-5,7,9-trienamide (104227-11-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) AlCl₃ / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) CH₂Cl₂, from 0 deg C to RT, 1 h

2: 38 percent / NaBH₄ / methanol / 0.5 h / 0 °C

3: 0.065 g / methanol / 2 h / Ambient temperature

With sodium tetrahydroborate; aluminium trichloride; In methanol;

DOI:10.1080/00397919308009765

upstream raw materials:

pyrrolidine

3-(4-methoxyphenyl)propionyl chloride

(1E,3E,5E)-1,6-bis(trimethylsilyl)hexa-1,3,5-triene

methyl (5E,7E,9E)-4,11-dioxo-13-(p-methoxyphenyl)-trideca-5,7,9-trienoate