Rauwolscine

Base Information

• Chemical Name: Rauwolscine
• CAS No.: 131-03-3
• Molecular Formula: C21H26 N2 O3
• Molecular Weight: 354.449
• European Community (EC) Number: 205-006-9
• UNII: T4LJ7LU45W
• DSSTox Substance ID: DTXSID2045608
• Nikkaji Number: J5.556E
• Wikipedia: Rauwolscine
• Wikidata: Q7296272
• Pharos Ligand ID: GL6W5QFSSVR4
• Metabolomics Workbench ID: 57044
• ChEMBL ID: CHEMBL10347
• Mol file: 131-03-3.mol

Synonyms:Aphrodine Hydrochloride;Aphrodyne;Corynanthine;Corynanthine Tartrate;Hydrochloride, Aphrodine;Hydrochloride, Yohimbine;Pluriviron;Rauhimbine;Rauwolscine;Tartrate, Corynanthine;Yocon;Yohimbin Spiegel;Yohimbine;Yohimbine Houdé;Yohimbine Hydrochloride;Yohimex

Chemical Property of Rauwolscine

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 243-244°
• Boiling Point: 543°Cat760mmHg
• PKA: 6.34(at 25℃)
• Flash Point: 282.2°C
• PSA: 65.56000
• Density: 1.31g/cm³
• LogP: 2.58500
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 354.19434270
• Heavy Atom Count: 26
• Complexity: 555

Purity/Quality:

99%, ^*data from raw suppliers

alpha-Yohimbine ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O
• Isomeric SMILES: COC(=O)[C@@H]1[C@H](CC[C@H]2[C@@H]1C[C@H]3C4=C(CCN3C2)C5=CC=CC=C5N4)O

Technology Process of Rauwolscine

There total 50 articles about Rauwolscine 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: 65.0%

methyl (4aS,13bS,14aS)-2-hydroxy-3,4,4a,5,7,8,13,13b,14,14adecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate (2671-54-7) → rauwolscine (131-03-3)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; water;

DOI:10.1021/jacs.9b12319

Reference yield: 52.9%

methyl (16α)-17-oxoyohimban-16-carboxylate (2114-90-1,2671-55-8,2671-57-0,18210-73-6,24204-01-1,40088-11-7,41904-77-2,59952-51-1,67711-33-5,83540-87-8,89015-76-9,114030-03-4) → (+/-)-β-yohimbine (84-37-7,131-03-3,146-48-5,483-09-0,483-10-3,522-92-9,522-94-1,549-82-6,549-84-8,2516-78-1,6835-85-4,24252-70-8,25920-66-5,40085-29-8,40085-30-1,40085-32-3,40088-19-5,40088-20-8,40088-25-3,41787-60-4,41904-78-3,59904-75-5,59952-52-2,59952-53-3,59952-56-6,83540-86-7,83540-88-9,103834-06-6,103834-07-7) + 3α-15α-20β-17α-hydroxylyohimbine-16α-carboxylic acid methyl ester (84-37-7,131-03-3,146-48-5,483-09-0,483-10-3,522-92-9,522-94-1,549-82-6,549-84-8,2516-78-1,6835-85-4,24252-70-8,25920-66-5,40085-29-8,40085-30-1,40085-32-3,40088-19-5,40088-20-8,40088-25-3,41787-60-4,41904-78-3,59904-75-5,59952-52-2,59952-53-3,59952-56-6,83540-86-7,83540-88-9,103834-06-6,103834-07-7)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.333333h;

DOI:10.1021/jo00008a025

Reference yield: 52.9%

methyl (16α)-17-oxoyohimban-16-carboxylate (2114-90-1,2671-55-8,2671-57-0,18210-73-6,24204-01-1,40088-11-7,41904-77-2,59952-51-1,67711-33-5,83540-87-8,89015-76-9,114030-03-4) → (+/-)-β-yohimbine (84-37-7,131-03-3,146-48-5,483-09-0,483-10-3,522-92-9,522-94-1,549-82-6,549-84-8,2516-78-1,6835-85-4,24252-70-8,25920-66-5,40085-29-8,40085-30-1,40085-32-3,40088-19-5,40088-20-8,40088-25-3,41787-60-4,41904-78-3,59904-75-5,59952-52-2,59952-53-3,59952-56-6,83540-86-7,83540-88-9,103834-06-6,103834-07-7) + 3α-15α-20β-17α-hydroxylyohimbine-16α-carboxylic acid methyl ester (84-37-7,131-03-3,146-48-5,483-09-0,483-10-3,522-92-9,522-94-1,549-82-6,549-84-8,2516-78-1,6835-85-4,24252-70-8,25920-66-5,40085-29-8,40085-30-1,40085-32-3,40088-19-5,40088-20-8,40088-25-3,41787-60-4,41904-78-3,59904-75-5,59952-52-2,59952-53-3,59952-56-6,83540-86-7,83540-88-9,103834-06-6,103834-07-7)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.333333h;

DOI:10.1021/jo00008a025

upstream raw materials:

17α-hydroxy-16β-methoxycarbonyl-20α-yohimba-3,5-dienium; chloride

potassium tert-butylate

benzene

alloyohimbine

Downstream raw materials:

17α-(toluene-4-sulfonyloxy)-20α-yohimban-16β-carboxylic acid methyl ester

17α-hydroxy-16β-methoxycarbonyl-4ξ-methyl-20α-yohimbanium; iodide

Yohimbine

rauwolscine hydrochloride

Refernces

• 1、 Le Hir,Warnhoff. "-". . p. 1564. Retrieved 1958.
• 2、 Miller, Eric R.,Hovey, M. Todd,Scheidt, Karl A.. "A Concise, Enantioselective Approach for the Synthesis of Yohimbine Alkaloids". . p. 2187 - 2192. Retrieved 2020/02/04.
• 3、 Miyata,Hirata,Naito,Ninomiya. "Novel total syntheses of (±)-yohimbine and (±)-alloyohimbine". . p. 1231 - 1232. Retrieved 2007/10/02.