protostephanine

Base Information

• Chemical Name: protostephanine
• CAS No.: 549-28-0
• Molecular Formula: C21H27NO4
• Molecular Weight: 357.44
• Mol file: 549-28-0.mol

Synonyms:Protostephanin;Protosephanin;2,3,10,12-Tetramethoxy-7-methyl-6,7,8,9-tetrahydro-5H-dibenz[d,f]azonin;6,7,8,9-Tetrahydro-2,3,10,12-tetramethoxy-7-methyl-5H-dibenzoazonin;2,3,10,12-tetramethoxy-7-methyl-6,7,8,9-tetrahydro-5H-dibenzo[d,f]azonine;

Chemical Property of protostephanine

Chemical Property:

• Vapor Pressure: 7.45E-11mmHg at 25°C
• Melting Point: 84-86° (Pecherer); mp 75° (Kondo)
• Boiling Point: 518.5°C at 760 mmHg
• PKA: 8.75±0.20(Predicted)
• Flash Point: 149.2°C
• PSA: 40.16000
• Density: 1.095g/cm³
• LogP: 3.35630

Purity/Quality:

PROTOSTEPHANINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: A Stephania alkaloid, this base is found in S. japonica Miers. It forms colourless prisms from MeOH which contain solvent of crystallization, m.p. 75°C. The solvent may be removed under vacuum when the dry alkaloid has a higher melting point of 90-S°C. It is optically inactive and yields crystalline saits, e.g. the hydrochloride, m.p. 150°C (dec.); platinichloride, orange prisms, m.p. 223°C (dec.); methiodide, m.p. 220-loC and the methomethylsulphate, m.p. 235°C after sintering at 227°C. The structure has recently been confirmed by a synthesis which follows a route related to the biosynthetic pathway.

Technology Process of protostephanine

There total 24 articles about protostephanine 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:

(4,5-dimethoxy-2-nitrophenyl)acetic acid (73357-18-3) → protostephanine (549-28-0)

Guidance literature:

Multi-step reaction with 10 steps

1: oxalyl chloride, dimethylformamide / benzene / 20 °C

2: sodium hydrogen carbonate / CHCl₃; diethyl ether; H₂O / 0.25 h

3: 81 percent / phosphorus oxychloride / CHCl₃ / 0.42 h / Heating

4: 84 percent / 3 h / Heating; in the dark

5: zinc dust, conc. hydrochloric acid / H₂O

6: 1.) 1 M sulphuric acid, sodium nitrite, 2.) copper powder / 1.) -3 deg C, 30 min, 2.) acetone, -3 deg C, 2 h

7: sodium borohydride / ethanol / 1 h / 0 °C

8: 89 percent / 6 M sulphuric acid / methanol / 0.67 h / 20 °C

9: 1.) magnesium iodide, 2.) lithium aluminium hydride / 1.) benzene, reflux, 1.5 h, 2.) ether, reflux, 2 h

10: diethyl ether

With hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; sulfuric acid; copper; sodium hydrogencarbonate; N,N-dimethyl-formamide; magnesium iodide; zinc; sodium nitrite; trichlorophosphate; In methanol; diethyl ether; ethanol; chloroform; water; benzene;

DOI:10.1039/P19810002002

Reference yield:

4,5-dimethoxy-2-nitrophenylacetic acid chloride (53602-52-1) → protostephanine (549-28-0)

Guidance literature:

Multi-step reaction with 9 steps

1: sodium hydrogen carbonate / CHCl₃; diethyl ether; H₂O / 0.25 h

2: 81 percent / phosphorus oxychloride / CHCl₃ / 0.42 h / Heating

3: 84 percent / 3 h / Heating; in the dark

4: zinc dust, conc. hydrochloric acid / H₂O

5: 1.) 1 M sulphuric acid, sodium nitrite, 2.) copper powder / 1.) -3 deg C, 30 min, 2.) acetone, -3 deg C, 2 h

6: sodium borohydride / ethanol / 1 h / 0 °C

7: 89 percent / 6 M sulphuric acid / methanol / 0.67 h / 20 °C

8: 1.) magnesium iodide, 2.) lithium aluminium hydride / 1.) benzene, reflux, 1.5 h, 2.) ether, reflux, 2 h

9: diethyl ether

With hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; sulfuric acid; copper; sodium hydrogencarbonate; magnesium iodide; zinc; sodium nitrite; trichlorophosphate; In methanol; diethyl ether; ethanol; chloroform; water;

DOI:10.1039/P19810002002

Reference yield:

4,5-dimethoxy-2-nitro-N-(3,4,5-trimethoxyphenethyl)phenylacetamide (79831-93-9) → protostephanine (549-28-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 81 percent / phosphorus oxychloride / CHCl₃ / 0.42 h / Heating

2: 84 percent / 3 h / Heating; in the dark

3: zinc dust, conc. hydrochloric acid / H₂O

4: 1.) 1 M sulphuric acid, sodium nitrite, 2.) copper powder / 1.) -3 deg C, 30 min, 2.) acetone, -3 deg C, 2 h

5: sodium borohydride / ethanol / 1 h / 0 °C

6: 89 percent / 6 M sulphuric acid / methanol / 0.67 h / 20 °C

7: 1.) magnesium iodide, 2.) lithium aluminium hydride / 1.) benzene, reflux, 1.5 h, 2.) ether, reflux, 2 h

8: diethyl ether

With hydrogenchloride; sodium tetrahydroborate; lithium aluminium tetrahydride; sulfuric acid; copper; magnesium iodide; zinc; sodium nitrite; trichlorophosphate; In methanol; diethyl ether; ethanol; chloroform; water;

DOI:10.1039/P19810002002

upstream raw materials:

diazomethane

11,12-Dimethoxy-7-methyl-6,7,8,9-tetrahydro-5H-dibenzo[d,f]azonine-2,4-diol

4,11,12-Trimethoxy-7-methyl-6,7,8,9-tetrahydro-5H-dibenzo[d,f]azonin-2-ol

C₂₁H₂₇NO₅

Refernces