Rhoeadine

Base Information

• Chemical Name: Rhoeadine
• CAS No.: 2718-25-4
• Molecular Formula: C₂₁H₂₁NO₆
• Molecular Weight: 383.401
• UNII: 9Q9C65WH3B
• DSSTox Substance ID: DTXSID10181652
• Nikkaji Number: J7.900F
• Wikipedia: Rhoeadine
• Wikidata: Q203455
• Mol file: 2718-25-4.mol

Synonyms:rhoeadine

Chemical Property of Rhoeadine

Chemical Property:

• Vapor Pressure: 1.01E-09mmHg at 25°C
• Melting Point: 222°C
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 489.3°Cat760mmHg
• PKA: 6.40±0.40(Predicted)
• Flash Point: 142.9°C
• PSA: 58.62000
• Density: 1.45g/cm³
• LogP: 3.02740
• Water Solubility.: 832.6mg/L(25 oC)
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 383.13688739
• Heavy Atom Count: 28
• Complexity: 591

Purity/Quality:

98%min ^*data from raw suppliers

(+)-Rheadine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC3=C(C=C2C4C1C5=C(C(O4)OC)C6=C(C=C5)OCO6)OCO3
• Isomeric SMILES: CN1CCC2=CC3=C(C=C2[C@@H]4[C@H]1C5=C([C@H](O4)OC)C6=C(C=C5)OCO6)OCO3
• Description: This alkaloid was found by Hesse in Papaver rhoeas Linn (red poppy) and its reputed existence in opium now appears doubtful. The base crystallizes from a mixture of CHCl3 and Et20 and sublimes at 21 5-225°C/0.02 mm. It has [α]17.5D + 232° (CHCI 3) or [α]19D + 243° (CHCl3). It behaves as a weak base and is sparingly soluble in H20, alkaline solutions and most organic solvents. It dissolves in mineral acids giving an intensely red solution but investigation shows that only a small proportion of the alkaloid is used to produce the colour, the major part being converted into a colourless, crystalline substance, Rhoeagenine, a much stronger base, non-volatile, and stable to acids. This base is not isomeric with the alkaloid as first thought but has the formula C2oH1906N, m.p. 236-8°C; [α]19D + l68° (AcOH).). Rhoeadine itself contains two methylenedioxy groups, one methoxy group and an N-methyl group. The salts are not easy to prepare but a crystalline hydriodide dihydrate is formed by addition of KI to a solution of the alkaloid in AcOH. The ultraviolet spectrum of the alkaloid shows absorption maxima at 205, 240 and 292 mμ.
• Uses: An isoquinoline alkaloid used in the therapeutic field particularly for the prevention and the treatment of pathologies implying a central and/or peripheral disorder. As an isoquinoline alkaloid, Rhoeadine can be used in the therapeutic field particularly for the prevention and the treatment of pathologies implying a central and/or peripheral disorder.

Technology Process of Rhoeadine

There total 9 articles about Rhoeadine 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:

methyl-{2-[6-(8-oxo-8H-furo[3',4':3,4]benzo[1,2-d][1,3]dioxol-6-ylidenemethyl)-benzo[1,3]dioxol-5-yl]-ethyl}-carbamic acid phenyl ester (35321-06-3) → rhoeadine (2718-25-4)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. NaOH

2: (i) AcOH, (ii) air

3: (i) LiBH₄, THF, (ii) AcOH

4: (i) sodium bis-(2-methoxy-ethoxy)-aluminium hydride, Py, (ii) /BRN= 969215/, MeOH, H⁺

With sodium hydroxide;

DOI:10.1002/hlca.19710540736

Reference yield:

methanol (67-56-1) + rhoeagenine (5574-77-6) → rhoeadine (2718-25-4)

Guidance literature:

With hydrogenchloride; Heating;

Reference yield:

5-(7-methyl-8,9-dihydro-7H-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]azepin-6-yl)-benzo[1,3]dioxole-4-carboxylic acid; sodium salt (35352-69-3) → rhoeadine (2718-25-4)

Guidance literature:

Multi-step reaction with 3 steps

1: (i) AcOH, (ii) air

2: (i) LiBH₄, THF, (ii) AcOH

3: (i) sodium bis-(2-methoxy-ethoxy)-aluminium hydride, Py, (ii) /BRN= 969215/, MeOH, H⁺

DOI:10.1002/hlca.19710540736

upstream raw materials:

2,3;10,11-bis-methanediyldioxy-16-methyl-rheadan-8-one

trimethyl orthoformate

methanol

rhoeagenine

Refernces

• 1、 Kloetzer,Teitel,Brossi. "A total synthesis of the alkaloid rhoeadine. Preliminary communication.". . p. 2057 - 2059. Retrieved 2007/10/04.