Aphelandrine

Base Information

• Chemical Name: Aphelandrine
• CAS No.: 69721-57-9
• Molecular Formula: C₂₈H₃₆N₄O₄
• Molecular Weight: 492.618
• UNII: 5FP0U18G3V
• Wikidata: Q27262003
• Mol file: 69721-57-9.mol

Synonyms:aphelandrine

Chemical Property of Aphelandrine

Chemical Property:

• Vapor Pressure: 5.06E-23mmHg at 25°C
• Boiling Point: 746.1°C at 760 mmHg
• Flash Point: 405°C
• PSA: 102.93000
• Density: 1.29g/cm³
• LogP: 3.67660
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 492.27365564
• Heavy Atom Count: 36
• Complexity: 743

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN2CCCNC(=O)CC(C3=CC4=C(C=C3)OC(C4C2=O)C5=CC=C(C=C5)O)NCCCNC1
• Isomeric SMILES: C1CCN2CCCNC(=O)C[C@@H](C3=CC4=C(C=C3)O[C@@H]([C@H]4C2=O)C5=CC=C(C=C5)O)NCCCNC1

Technology Process of Aphelandrine

There total 10 articles about Aphelandrine 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:

(-)-(8S)-1-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-8-(4-hydroxyphenyl)-1,5,9,13-tetraazacycloheptadecan-6-one (312908-82-0) → (11S,17S,18S)-aphelandrine (69721-57-9)

Guidance literature:

With soluble protein fraction of barley seedlings; In phosphate buffer; at 25 ℃; for 1h; pH=7.4;

DOI:10.1016/S0040-4039(01)00670-0

Reference yield:

(-)-(8S)-1-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-8-(4-hydroxyphenyl)-1,5,9,13-tetraazacycloheptadecan-6-one (312908-82-0) → chaenorpine (114622-14-9) + (11S,17S,18S)-aphelandrine (69721-57-9) + (-)-ephedradine A (71461-13-7)

Guidance literature:

With hemin; dihydrogen peroxide; potassium carbonate; In water; acetonitrile; at 20 ℃; for 0.166667h;

DOI:10.1002/1522-2675(20010711)84:7<2108::AID-HLCA2108>3.0.CO;2-G

Reference yield:

(E)-3-(4-methoxyphenyl)acrylic acid (943-89-5) → (11S,17S,18S)-aphelandrine (69721-57-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: HCHO

1.2: 2-chloro-N-methylpyridinium iodide

1.3: 75 percent / NH₂OH*HCl

2.1: 98 percent / BBr₃ / CH₂Cl₂

3.1: hemin; K₂CO₃; 10 percent H₂O₂ / acetonitrile; H₂O / 0.17 h / 20 °C

With formaldehyd; hemin; dihydrogen peroxide; boron tribromide; potassium carbonate; In dichloromethane; water; acetonitrile;

DOI:10.1002/1522-2675(20010711)84:7<2108::AID-HLCA2108>3.0.CO;2-G

upstream raw materials:

(-)-(8S)-1-[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-8-(4-hydroxyphenyl)-1,5,9,13-tetraazacycloheptadecan-6-one

(E)-3-(4-methoxyphenyl)acrylic acid

(-)-(S)-8-(4-methoxyphenyl)-1,5,9,13-tetraazacycloheptadecan-6-one

(-)-(8S)-1-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]-8-(4-methoxyphenyl)-1,5,9,13-tetraazacycloheptadecan-6-one

Downstream raw materials:

(-)-ephedradine A