(αE)-α-Ethylidene-1,2,3,3aα,4,5,6,7-octahydro-7α-hydroxy-3-methyl-3,7a-diazacyclohepta[jk]fluorene-5β-acetaldehyde

Base Information

• Chemical Name: (αE)-α-Ethylidene-1,2,3,3aα,4,5,6,7-octahydro-7α-hydroxy-3-methyl-3,7a-diazacyclohepta[jk]fluorene-5β-acetaldehyde
• CAS No.: 56519-07-4
• Molecular Formula: C20H24N2O2
• Molecular Weight: 324.4168
• Mol file: 56519-07-4.mol

Synonyms:(E)-2-((3aS,5R,7S)-7-Hydroxy-3-methyl-1,2,3,3a,4,5,6,7-octahydro-3,7a-diaza-cyclohepta[jk]fluoren-5-yl)-but-2-enal;Akagerin;Aragerin;2-(7-hydroxy-3-methyl-1,2,3,3a,4,5,6,7-octahydro-3,7a-diaza-cyclohepta[jk]fluoren-5-yl)-but-2-enal;akagerine;

Chemical Property of (αE)-α-Ethylidene-1,2,3,3aα,4,5,6,7-octahydro-7α-hydroxy-3-methyl-3,7a-diazacyclohepta[jk]fluorene-5β-acetaldehyde

Chemical Property:

• Vapor Pressure: 1.5E-12mmHg at 25°C
• Melting Point: 185 - 186 °C (ethyl acetate)
• Boiling Point: 541.3°Cat760mmHg
• Flash Point: 281.2°C
• PSA: 45.47000
• Density: 1.27g/cm³
• LogP: 3.15430

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (αE)-α-Ethylidene-1,2,3,3aα,4,5,6,7-octahydro-7α-hydroxy-3-methyl-3,7a-diazacyclohepta[jk]fluorene-5β-acetaldehyde

There total 10 articles about (αE)-α-Ethylidene-1,2,3,3aα,4,5,6,7-octahydro-7α-hydroxy-3-methyl-3,7a-diazacyclohepta[jk]fluorene-5β-acetaldehyde 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: 96.0%

(-)-17-O-Methylakagerine → akagerine (56519-07-4)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1021/jo00113a034

Reference yield: 88.0%

C27H38N2O4Si → (–)-akagerine (56519-07-4)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 6.5h; Inert atmosphere;

DOI:10.1002/chem.202104052

Reference yield:

C16H26O5Si → (–)-akagerine (56519-07-4)

Guidance literature:

Multi-step reaction with 4 steps

1: trifluoroacetic acid / dichloromethane / 1.5 h / 0 °C / Molecular sieve; Inert atmosphere

2: acetic acid; sodium cyanoborohydride / methanol / 60 h / 20 °C / Inert atmosphere

3: acetic acid / tetrahydrofuran; water / 3 h / -40 °C / Inert atmosphere

4: acetic acid; tetrabutyl ammonium fluoride / tetrahydrofuran / 6.5 h / 20 °C / Inert atmosphere

With tetrabutyl ammonium fluoride; sodium cyanoborohydride; acetic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1002/chem.202104052

upstream raw materials:

(-)-secologanin aglucone-O-silyl ether

palicoside

Refernces

• 1、 Sakamoto, Jukiya,Ishikawa, Hayato. "Bioinspired Transformations Using Strictosidine Aglycones: Divergent Total Syntheses of Monoterpenoid Indole Alkaloids in the Early Stage of Biosynthesis". . . Retrieved 2021/12/24.