Hirsuteine

Base Information

• Chemical Name: Hirsuteine
• CAS No.: 35467-43-7
• Molecular Formula: C22H26N2O3
• Molecular Weight: 366.4534
• UNII: 43X9C2G2W5
• DSSTox Substance ID: DTXSID201046112
• Wikipedia: Hirsuteine
• Wikidata: Q15634135
• Mol file: 35467-43-7.mol

Synonyms:hirsuteine;hirsuteine hydrochloride;hirsuteine, (3beta,16E)-isomer;hirsuteine, (R-(R*,R*))-tartrate (1:1) salt

Chemical Property of Hirsuteine

Chemical Property:

• Vapor Pressure: 1.89E-11mmHg at 25°C
• Boiling Point: 533.2°Cat760mmHg
• PKA: 18.03±0.60(Predicted)
• Flash Point: 276.3°C
• PSA: 54.56000
• Density: 1.22g/cm³
• LogP: 3.53040
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 366.19434270
• Heavy Atom Count: 27
• Complexity: 604

Purity/Quality:

99.3% ^*data from raw suppliers

Hirsuteine ≥99.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC=C(C1CC2C3=C(CCN2CC1C=C)C4=CC=CC=C4N3)C(=O)OC
• Isomeric SMILES: CO/C=C(\[C@H]1C[C@@H]2C3=C(CCN2C[C@@H]1C=C)C4=CC=CC=C4N3)/C(=O)OC

Technology Process of Hirsuteine

There total 11 articles about Hirsuteine 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:

C17H16N2O2 (112547-37-2,125279-31-4) → (+/-)-hirsuteine (18904-54-6,25920-83-6,35467-43-7,57820-49-2,112574-82-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / H₂ / PtO₂

2: -78 - 10 °C

3: Bu₃P

4: H₂O₂

5: aluminum hydride

6: LDA / -40 °C

7: 1.) HCl / 1.) MeOH

With aluminium hydride; hydrogenchloride; tributylphosphine; hydrogen; dihydrogen peroxide; lithium diisopropyl amide; platinum(IV) oxide;

Reference yield:

C17H18N2O2 (112547-38-3) → (+/-)-hirsuteine (18904-54-6,25920-83-6,35467-43-7,57820-49-2,112574-82-0)

Guidance literature:

Multi-step reaction with 6 steps

1: -78 - 10 °C

2: Bu₃P

3: H₂O₂

4: aluminum hydride

5: LDA / -40 °C

6: 1.) HCl / 1.) MeOH

With aluminium hydride; hydrogenchloride; tributylphosphine; dihydrogen peroxide; lithium diisopropyl amide;

Reference yield:

((2S,3S,12bS)-3-Vinyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl)-acetic acid tert-butyl ester (112547-43-0) → (+/-)-hirsuteine (18904-54-6,25920-83-6,35467-43-7,57820-49-2,112574-82-0)

Guidance literature:

Multi-step reaction with 2 steps

1: LDA / -40 °C

2: 1.) HCl / 1.) MeOH

With hydrogenchloride; lithium diisopropyl amide;

upstream raw materials:

diazomethane

3-Oxo-2-((2R,3S,12bS)-3-vinyl-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-2-yl)-propionic acid tert-butyl ester

C₁₇H₁₆N₂O₂

C₁₇H₁₈N₂O₂

Downstream raw materials:

dihydrocorynantheine

Refernces

• 1、 Scott,Cherry,Qureshi. "Mechanisms of indole alkaloid biosynthesis. The Corynanthe-Strychnos relationship.". . p. 4932 - 4933. Retrieved 2007/10/05.