Corynoxine B

Base Information

• Chemical Name: Corynoxine B
• CAS No.: 17391-18-3
• Molecular Formula: C₂₂H₂₈N₂O₄
• Molecular Weight: 384.475
• Mol file: 17391-18-3.mol

Synonyms:Corynoxine B;

Chemical Property of Corynoxine B

Chemical Property:

• Boiling Point: 560.8±50.0 °C(Predicted)
• PKA: 13.61±0.60(Predicted)
• PSA: 67.87000
• Density: 1.23±0.1 g/cm3(Predicted)
• LogP: 2.77610

Purity/Quality:

99% ^*data from raw suppliers

Corynoxine B ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Corynoxine B is an oxindole alkaloid isolated from Uncaria rhynchophylla (Miq.) Jacks (Gouteng in Chinese); a Beclin-1-dependent autophagy inducer.

Technology Process of Corynoxine B

There total 16 articles about Corynoxine B 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: 97.0%

(±)-corynoxeine (630-94-4,51014-29-0) → rhynchophylline (76-66-4,6859-01-4,6877-32-3,17391-18-3,39032-61-6,39032-62-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; for 18h; under 760.051 Torr;

DOI:10.1002/ejoc.201201505

Reference yield:

C25H29N3O8S → rhynchophylline (76-66-4,6859-01-4,6877-32-3,17391-18-3,39032-61-6,39032-62-7)

Guidance literature:

Multi-step reaction with 6 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

5.3: 20 h / 20 °C

6.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 18 h / 760.05 Torr

With bis(η3-allyl-μ-chloropalladium(II)); palladium 10% on activated carbon; hydrogen; potassium carbonate; caesium carbonate; thiophenol; triethylamine; N-ethyl-N,N-diisopropylamine; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; dimethyl sulfoxide; ethyl acetate; acetonitrile; 5.2: |Wittig Olefination;

DOI:10.1002/ejoc.201201505

Reference yield:

C19H26N2O4 (1443767-64-3) → rhynchophylline (76-66-4,6859-01-4,6877-32-3,17391-18-3,39032-61-6,39032-62-7)

Guidance literature:

Multi-step reaction with 5 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

4.3: 20 h / 20 °C

5.1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 18 h / 760.05 Torr

With bis(η3-allyl-μ-chloropalladium(II)); palladium 10% on activated carbon; hydrogen; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; ethyl acetate; 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

Refernces

• 1、 Finch,N.,Taylor,W.I.. "-". . p. 3871 - 3877. Retrieved 1962.
• 2、 Brown et al.. "-". . p. 1401. Retrieved 1976.
• 3、 -. "Process for the production of specific isomer mixtures from oxindole alkaloids". . . Retrieved 2008/06/13.