Corynoloxine

Base Information

• Chemical Name: Corynoloxine
• CAS No.: 31470-65-2
• Molecular Formula: C₂₁H₁₉NO₅
• Molecular Weight: 365.386
• Mol file: 31470-65-2.mol

Synonyms:4H-Bis[1,3]benzodioxolo[4,5-c:5',6'-g][1]benzopyran-4,12-imine,5a,6,12,12a-tetrahydro-12a,15-dimethyl-, (4S,5aS,12R,12aR)- (9CI); Chelidonine,11-deoxy-6,11-epoxy-13-methyl-, (6b,11b)-; Corynoloxine (8CI);(+)-Corynoloxine; Dehydrocorynoline

Chemical Property of Corynoloxine

Chemical Property:

• PSA: 49.39000
• LogP: 2.97980

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Corynoloxine

There total 8 articles about Corynoloxine 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: 95.0%

Corynoline (18797-79-0) → (+)-corynoloxine (31470-65-2)

Guidance literature:

With iodine; potassium acetate; potassium carbonate; In ethanol; for 2h; Reflux; Inert atmosphere;

DOI:10.1021/jacs.9b08441

Reference yield:

(+/-)-corycavine (521-87-9) → corynoloxine (31470-65-2)

Guidance literature:

With recombinant Eschscholzia californica P₄₅₀ CYP₈₂N₂v2; NADPH; In aq. buffer; at 30 ℃; for 0.5h; pH=7.6; Enzymatic reaction;

DOI:10.1016/j.phytochem.2012.02.013

Reference yield:

benzyl ((1R,2R)-1-(benzo[d][1,3]dioxol-5-yl)-2-(4-(((tertbutyldimethylsilyl)oxy)methyl)benzo[d][1,3]dioxol-5-yl)-2-methylbut-3-yn-1-yl)carbamate → (+)-corynoloxine (31470-65-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 1 h / 0 - 20 °C / Inert atmosphere

1.2: 3 h / 20 °C / Inert atmosphere

2.1: [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold bis(trifluoromethanesulfonyl)imidate / toluene / 0.03 h / 20 °C / Inert atmosphere

3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / toluene / 1 h / 20 - 80 °C

4.1: dihydrogen peroxide; formic acid / tetrahydrofuran; water / 20 °C

4.2: 0.08 h / 20 °C

4.3: 0.5 h / 20 °C / pH > 10

5.1: triethylsilane; boron trifluoride diethyl etherate / 1,2-dichloro-ethane / 5 h / 20 °C / Inert atmosphere

6.1: potassium carbonate; potassium acetate; iodine / ethanol / 2 h / Reflux; Inert atmosphere

With triethylsilane; formic acid; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene]gold bis(trifluoromethanesulfonyl)imidate; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; dihydrogen peroxide; iodine; potassium acetate; potassium carbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; toluene;

DOI:10.1021/jacs.9b08441

upstream raw materials:

(+/-)-corycavine

Corynoline

(11SR,13RS,14RS)-corynoline

Refernces

• 1、 Trost, Barry M.,Hung, Chao-I Joey,Jiao, Zhiwei. "Enantioselective Divergent Syntheses of (+)-Bulleyanaline and Related Isoquinoline Alkaloids from the Genus Corydalis". . p. 16085 - 16092. Retrieved 2019.