(15bS)-9,10,15b,16-Tetrahydro-5,15-dimethoxy-1H,7H-[1,3]benzodioxino[6,5-g][1,3]benzodioxolo[5,6-a]quinolizine

Base Information

• Chemical Name: (15bS)-9,10,15b,16-Tetrahydro-5,15-dimethoxy-1H,7H-[1,3]benzodioxino[6,5-g][1,3]benzodioxolo[5,6-a]quinolizine
• CAS No.: 23943-90-0
• Molecular Formula: C₂₂H₂₃NO₆
• Molecular Weight: 397.428
• Mol file: 23943-90-0.mol

Synonyms:1H,7H-[1,3]Benzodioxino[6,5-g][1,3]benzodioxolo[5,6-a]quinolizine,9,10,15b,16-tetrahydro-5,15-dimethoxy-, (S)-; Bractavine; Orientalidine

Chemical Property of (15bS)-9,10,15b,16-Tetrahydro-5,15-dimethoxy-1H,7H-[1,3]benzodioxino[6,5-g][1,3]benzodioxolo[5,6-a]quinolizine

Chemical Property:

• Vapor Pressure: 4.83E-12mmHg at 25°C
• Melting Point: 196-8°C
• Boiling Point: 547.5°Cat760mmHg
• Flash Point: 160.7°C
• PSA: 58.62000
• Density: 1.42g/cm³
• LogP: 2.89240

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: This alkaloid from Papaver orientale forms colourless crystals from AcOEt and has [α] 22 D- 254° ± 4° (c 0.31, MeOH). It forms a methiodide, m.p. 252-3°C, a methine, m.p. 195-7°C and dimethine, m.p. l46-8°C. Exhaustive methylation gives trimethylamine and a nitrogen-free oil as the final products. Oxidation of the alkaloid with chromic acid or KMn04 yields Alkaloid PO-4 (q.v.). When refluxed with 5 per cent H2S04 the base yields formaldehyde which may arise from either the hydrolysis of the methylenedioxy group or, more probably, that of the 1: 3-benzodioxan group.

Technology Process of (15bS)-9,10,15b,16-Tetrahydro-5,15-dimethoxy-1H,7H-[1,3]benzodioxino[6,5-g][1,3]benzodioxolo[5,6-a]quinolizine

There total 9 articles about (15bS)-9,10,15b,16-Tetrahydro-5,15-dimethoxy-1H,7H-[1,3]benzodioxino[6,5-g][1,3]benzodioxolo[5,6-a]quinolizine 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:

8-methoxy-6,7-methylenedioxyisoquinoline (5361-66-0) → (+/-)-Orientalidin (22325-09-3,23943-90-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 61 percent / CH₂Cl₂; H₂O / 1 h / Ambient temperature

2: NaH / dimethylformamide / 1.) -20 deg C, 2 h; 2.) room temperature, 3 h

3: 58 percent / sodium hydroxide / ethanol; H₂O / 2.5 h / Heating

4: 79 percent / Zn/HCl / ethanol / 3 h / Heating

5: 74 percent / H₂ / PtO₂ / ethanol / 24 h / 3750.3 Torr / Ambient temperature

6: 56 percent / ethanol / 1 h / Heating

7: 63 percent / sodium hydroxide / methanol / Ambient temperature

8: 0.075 g / NaH / dimethylformamide

With hydrogenchloride; sodium hydroxide; hydrogen; sodium hydride; zinc; platinum(IV) oxide; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

3-benzyloxy-4-methoxy-benzyl chloride (1699-38-3) → (+/-)-Orientalidin (22325-09-3,23943-90-0)

Guidance literature:

Multi-step reaction with 7 steps

1: NaH / dimethylformamide / 1.) -20 deg C, 2 h; 2.) room temperature, 3 h

2: 58 percent / sodium hydroxide / ethanol; H₂O / 2.5 h / Heating

3: 79 percent / Zn/HCl / ethanol / 3 h / Heating

4: 74 percent / H₂ / PtO₂ / ethanol / 24 h / 3750.3 Torr / Ambient temperature

5: 56 percent / ethanol / 1 h / Heating

6: 63 percent / sodium hydroxide / methanol / Ambient temperature

7: 0.075 g / NaH / dimethylformamide

With hydrogenchloride; sodium hydroxide; hydrogen; sodium hydride; zinc; platinum(IV) oxide; In methanol; ethanol; water; N,N-dimethyl-formamide;

Reference yield:

1-(3-hydroxy-4-methoxybenzyl)-8-methoxy-6,7-methylenedioxyisoquinoline (79659-41-9) → (+/-)-Orientalidin (22325-09-3,23943-90-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 74 percent / H₂ / PtO₂ / ethanol / 24 h / 3750.3 Torr / Ambient temperature

2: 56 percent / ethanol / 1 h / Heating

3: 63 percent / sodium hydroxide / methanol / Ambient temperature

4: 0.075 g / NaH / dimethylformamide

With sodium hydroxide; hydrogen; sodium hydride; platinum(IV) oxide; In methanol; ethanol; N,N-dimethyl-formamide;

upstream raw materials:

dichloromethane

11-hydroxy-12-hydroxymethyl-1,10-dimethoxy-2,3-methylenedioxyberbine

8-methoxy-6,7-methylenedioxyisoquinoline

11-hydroxy-1,10-dimethoxy-2,3-methylenedioxyberbine

Refernces