allo-Yohimbine

Base Information

• Chemical Name: allo-Yohimbine
• CAS No.: 522-94-1
• Molecular Formula: C21H26 N2 O3
• Molecular Weight: 354.449
• UNII: 60AHA8MSG9
• DSSTox Substance ID: DTXSID601317509
• Nikkaji Number: J6.628A
• Wikidata: Q27121267
• Metabolomics Workbench ID: 57046
• ChEMBL ID: CHEMBL1526082
• Mol file: 522-94-1.mol

Synonyms:allo-Yohimbine;Alloyohimbine;Alloyohimbin;522-94-1;UNII-60AHA8MSG9;60AHA8MSG9;CHEBI:48567;Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16-alpha,17-alpha,20-alpha)-;methyl 17alpha-hydroxy-20alpha-yohimban-16alpha-carboxylate;methyl (16alpha,17alpha,20alpha)-17-hydroxyyohimban-16-carboxylate;(16alpha,17alpha,20alpha)-17-hydroxyyohimban-16-carboxylic acid methyl ester;ALLO-YOHIMBINE [MI];SCHEMBL453033;CHEMBL1526082;DTXSID601317509;AKOS040750337;NCGC00025018-02;NCGC00025018-03;NCGC00025018-04;LS-162740;Q27121267;(1r,2s,4as,13bs,14aS)-2-hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester, AldrichCPR;methyl (1S,15S,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;YOHIMBAN-16-CARBOXYLIC ACID, 17-HYDROXY-, METHYL ESTER, (16.ALPHA.,17.ALPHA.,20.ALPHA.)-

Chemical Property of allo-Yohimbine

Chemical Property:

• Vapor Pressure: 1.27E-12mmHg at 25°C
• Melting Point: 98-99°; anhydrous form melts at 135-140°
• Boiling Point: 543°Cat760mmHg
• 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:

98%min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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 allo-Yohimbine

There total 35 articles about allo-Yohimbine 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: 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

Reference yield:

tryptamine (61-54-1) → 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:

Multi-step reaction with 7 steps

1: 90 percent / potassium carbonate / ethanol; H₂O / 0.5 h / Heating

2: 1) m-(chloroperoxy)benzoic acid, 2) triethylamine, acetic anhydride / 1) diethyl ether/dichloromethane, 0 to 20 deg C, 2 h, 2) CH₂Cl₂, 0 deg C, 30 min

3: 95 percent / CH₂Cl₂ / 0.5 h / 20 °C

4: 1) 1,4-diazabicyclo<5.4.0>undec-7-ene (DBU) / 1) N,N-dimethylacetamide, 2) a) 20 deg C, 1h, b) 70 deg C, 1h

5: 50 percent / 50percent aq. sulfuric acid / methanol / 24 h / 20 °C

6: 65.6 percent / conc. hydrochloric acid, H₂ / 10percent Pd-C / methanol / 18 h / 20 °C / 760 Torr

7: 22.2 percent / sodium borohydride / methanol / 0.33 h / 0 °C

With hydrogenchloride; sodium tetrahydroborate; 1,4-diazabicyclo[5.4.0]-7-undecene; sulfuric acid; hydrogen; acetic anhydride; potassium carbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In methanol; ethanol; dichloromethane; water;

DOI:10.1021/jo00008a025

upstream raw materials:

methyl (16α)-17-oxoyohimban-16-carboxylate

19,20-didehydroyohimban-17-one

(20β)-18,19-didehydroyohimban-17-one

dimethyl (16α)-17-oxoyohimban-1,16-dicarboxylate

Downstream raw materials:

rauwolscine

Yohimbine

Refernces

• 1、 Miyata,Hirata,Naito,Ninomiya. "Novel total syntheses of (±)-yohimbine and (±)-alloyohimbine". . p. 1231 - 1232. Retrieved 2007/10/02.
• 2、 Szantay,Toeke,Honti. "Synthesis of (+)-yohimbine and (+)-beta-yohimbine. A new route to yohimban ring system.". . p. 1665 - 1670. Retrieved 2007/10/04.