Perakine

Base Information

• Chemical Name: Perakine
• CAS No.: 4382-56-3
• Molecular Formula: C21H22N2O3
• Molecular Weight: 350.411
• Mol file: 4382-56-3.mol

Synonyms:18-Norajmalan-19-al, 17-(acetyloxy)-1,2-didehydro-1-demethyl-21-methyl-, (17R,20alpha,21beta)-;Raucaffrine;18-Norajmalan-19-al,17-(acetyloxy)-1,2- didehydro-1-demethyl-21-methyl-,(17R,20R,- 21a)-;18-Norajmalan-19-al, 17-(acetyloxy)-1,2-didehydro-1-demethyl-21-methyl-, (17R,20a,21b)-;Indole alkaloid;

Chemical Property of Perakine

Chemical Property:

• Vapor Pressure: 7.42E-10mmHg at 25°C
• Melting Point: 186 °C
• Refractive Index: 1.804
• Boiling Point: 492.8 °C at 760 mmHg
• PKA: 5.38±0.70(Predicted)
• Flash Point: 251.9 °C
• PSA: 58.97000
• Density: 1.59 g/cm³
• LogP: 1.62550

Purity/Quality:

98%,99%, ^*data from raw suppliers

Perakine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: This alkaloid has been shown to be identical with Perakine (q.v.).
• Uses: Perakine is an alkaloid extracted from family of Rauvolfia plants which acts as an inhibitor of aldose reductase, a potent drug target for diabetes.

Technology Process of Perakine

There total 11 articles about Perakine 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:

C22H32N4O (2552-93-4) → Perakine (4382-56-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 1 N NaOH / CH₂Cl₂ / 0.67 h / Ambient temperature

2: 86 percent / H₂O, CuCl₂ / tetrahydrofuran / 36 h / Ambient temperature; pH 7 (phosphate buffer)

3: 93 percent / pyridine / Ambient temperature

4: 88 percent / lead tetraacetate / CH₂Cl₂ / 1 h / -70 to 0 deg C

5: triethylamine / CH₂Cl₂ / 5 h / Ambient temperature

6: N-bromosuccinimide, triethylamine / CH₂Cl₂ / 0.17 h / 0 °C

7: 21 percent / Li₂CO₃ / dimethylformamide / 4.5 h / 80 °C

8: 75 percent / zinc dust, acetic acid / 1.5 h / Ambient temperature

9: acetic acid / 336 h / Ambient temperature

With pyridine; lead(IV) acetate; sodium hydroxide; N-Bromosuccinimide; water; lithium carbonate; acetic acid; triethylamine; copper dichloride; zinc; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1248/cpb.39.266

Reference yield:

C23H27Cl3N2O4 (134310-02-4) → Perakine (4382-56-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / pyridine / Ambient temperature

2: 88 percent / lead tetraacetate / CH₂Cl₂ / 1 h / -70 to 0 deg C

3: triethylamine / CH₂Cl₂ / 5 h / Ambient temperature

4: N-bromosuccinimide, triethylamine / CH₂Cl₂ / 0.17 h / 0 °C

5: 21 percent / Li₂CO₃ / dimethylformamide / 4.5 h / 80 °C

6: 75 percent / zinc dust, acetic acid / 1.5 h / Ambient temperature

7: acetic acid / 336 h / Ambient temperature

With pyridine; lead(IV) acetate; N-Bromosuccinimide; lithium carbonate; acetic acid; triethylamine; zinc; In dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1248/cpb.39.266

Reference yield:

C24H25Cl3N2O5 (134276-99-6) → Perakine (4382-56-3)

Guidance literature:

Multi-step reaction with 5 steps

1: triethylamine / CH₂Cl₂ / 5 h / Ambient temperature

2: N-bromosuccinimide, triethylamine / CH₂Cl₂ / 0.17 h / 0 °C

3: 21 percent / Li₂CO₃ / dimethylformamide / 4.5 h / 80 °C

4: 75 percent / zinc dust, acetic acid / 1.5 h / Ambient temperature

5: acetic acid / 336 h / Ambient temperature

With N-Bromosuccinimide; lithium carbonate; acetic acid; triethylamine; zinc; In dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1248/cpb.39.266

upstream raw materials:

(19Z)-Vomilenine

C₂₂H₃₂N₄O

C₂₃H₂₇Cl₃N₂O₄

C₂₄H₂₅Cl₃N₂O₅

Refernces

• 1、 Takayama,Phisalaphong,Kitajima,Aimi,Sakai,Stockigt. "Partial synthesis of Rauwolfia alkaloids, vomilenine and (19Z)-vomilenine, and their relative thermodynamic stability as revealed by their transformation into perakine". . p. 266 - 269. Retrieved 2007/10/02.