corynoxeine

Base Information

• Chemical Name: corynoxeine
• CAS No.: 630-94-4
• Molecular Formula: C₂₂H₂₆N₂O₄
• Molecular Weight: 382.459
• Hs Code.: 2933998090
• Mol file: 630-94-4.mol

Synonyms:Corynoxan-16-carboxylicacid, 16,17,18,19-tetradehydro-17-methoxy-2-oxo-, methyl ester, (7b,16E,20a)-;Corynoxeine (6CI,7CI);Corynoxein;Spiro[3H-indole-3,1'(5'H)-indolizine]-7'-acetic acid,6'-ethenyl-1,2,2',3',6',7',8',8'a-octahydro-a-(methoxymethylene)-2-oxo-, methyl ester, [1'R-[1'a,6'b,7'a(E),8'ab]]-;D18-Rhyncophylline;d18-Rhynchophylline;Corynoxeine;(+/-)-corynoxeine;ISOCORYNOXEINE;

Chemical Property of corynoxeine

Chemical Property:

• Appearance/Colour: white poweder
• Vapor Pressure: 1.09E-12mmHg at 25°C
• Melting Point: 210 oC
• Refractive Index: 1.605
• Boiling Point: 562.7°C at 760 mmHg
• PKA: 13.54±0.60(Predicted)
• Flash Point: 294.1°C
• PSA: 67.87000
• Density: 1.25
• LogP: 2.55210

Purity/Quality:

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

Corynoxeine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Corynoxeine is an alkaloid isolated from extraction of Uncaria rhynchophylla, is useful in the treatment of vascular diseases and protection against ischemia-induced neuronal damage.

Technology Process of corynoxeine

There total 12 articles about corynoxeine 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:

C20H22N2O4 + potassium tert-butylate (865-47-4) + (methoxymethyl)triphenylphosphonium chloride (4009-98-7) → (±)-corynoxeine (630-94-4,51014-29-0)

Guidance literature:

potassium tert-butylate; (methoxymethyl)triphenylphosphonium chloride; In tetrahydrofuran; at 20 ℃; for 0.0833333h;

C₂₀H₂₂N₂O₄; In tetrahydrofuran; at -78 - 20 ℃;

With trifluoroacetic acid; trifluoroacetic anhydride; In dichloromethane; at 20 ℃; for 20h;

DOI:10.1002/ejoc.201201505

Reference yield:

C25H29N3O8S → (±)-corynoxeine (630-94-4,51014-29-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: thiophenol; potassium carbonate / dimethyl sulfoxide / 2.15 h

2.1: triethylamine / acetonitrile / 2.33 h / 20 °C

3.1: caesium carbonate; N-ethyl-N,N-diisopropylamine; 1,2-bis-(diphenylphosphino)ethane; bis(η3-allyl-μ-chloropalladium(II)) / tetrahydrofuran / 8 h / Inert atmosphere

4.1: 6 h / 0 °C

5.1: tetrahydrofuran / 0.08 h / 20 °C

5.2: -78 - 20 °C

With bis(η3-allyl-μ-chloropalladium(II)); potassium carbonate; caesium carbonate; thiophenol; triethylamine; N-ethyl-N,N-diisopropylamine; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; dimethyl sulfoxide; acetonitrile; 5.2: |Wittig Olefination;

DOI:10.1002/ejoc.201201505

Reference yield:

C19H26N2O4 (1443767-64-3) → (±)-corynoxeine (630-94-4,51014-29-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / acetonitrile / 2.33 h / 20 °C

2.1: caesium carbonate; N-ethyl-N,N-diisopropylamine; 1,2-bis-(diphenylphosphino)ethane; bis(η3-allyl-μ-chloropalladium(II)) / tetrahydrofuran / 8 h / Inert atmosphere

3.1: 6 h / 0 °C

4.1: tetrahydrofuran / 0.08 h / 20 °C

4.2: -78 - 20 °C

With bis(η3-allyl-μ-chloropalladium(II)); caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; acetonitrile; 4.2: |Wittig Olefination;

DOI:10.1002/ejoc.201201505

upstream raw materials:

C₁₉H₂₆N₂O₄

tert-butyl 2-oxohex-5-enoate

tryptamine

tert-butyl 2,5-dioxopentanoate

Downstream raw materials:

rhynchophylline

Refernces