Koumine

Base Information

• Chemical Name: Koumine
• CAS No.: 1358-76-5
• Molecular Formula: C₂₀H₂₂N₂O
• Molecular Weight: 306.407
• Mol file: 1358-76-5.mol

Synonyms:Koumine;

Chemical Property of Koumine

Chemical Property:

• Melting Point: 168℃
• Refractive Index: 1.763
• Boiling Point: 436.5 °C at 760 mmHg
• PKA: 8.67±0.40(Predicted)
• Flash Point: 217.8 °C
• PSA: 24.83000
• Density: 1.42 g/cm³
• LogP: 2.30900
• Storage Temp.: 2-8°C

Purity/Quality:

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

Koumine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: The Chinese drug 'Kou-wen', said to be derived from Gelsemium elegans Benth., is stated to contain this alkaloid which forms rhombic prisms from Me2 CO. It has [α]23D - 265° (EtOH) and forms a crystalline hydrochloride, m.p. 255°C (dec.) and a hydrobromide, m.p. 269°C (dec.).
• Uses: Koumine is known to attenuate the lipopolysaccharide-stimulated inflammation in RAW264.7 macrophages.

Technology Process of Koumine

There total 48 articles about Koumine 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: 74.0%

C22H26N2O3 → (-)-koumine (1358-76-5,83705-29-7,119241-69-9)

Guidance literature:

C₂₂H₂₆N₂O₃; With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 0.25h; Inert atmosphere;

With palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 90 ℃; for 3h; Inert atmosphere;

DOI:10.1021/acs.orglett.6b00661

Reference yield:

C33H33NO4 → (-)-koumine (1358-76-5,83705-29-7,119241-69-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: potassium carbonate / methanol; tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

2.1: pyridine / tetrahydrofuran; toluene / 2 h / -78 - -40 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

3.2: 1.5 h / -78 °C / Inert atmosphere

4.1: toluene-4-sulfonic acid / methanol / 8 h / 20 °C / Inert atmosphere

5.1: pyridine; pyridine hydrochloride / 23 h / 100 °C / Inert atmosphere

6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

6.2: 2 h / 0 - 20 °C / Inert atmosphere

7.1: ammonia; sodium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere

8.1: tetrahydrofuran; water / 4.5 h / 0 - 20 °C / Inert atmosphere

9.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

10.1: pyridine / 1 h / 0 - 20 °C / Inert atmosphere

11.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C / Inert atmosphere

11.2: 3 h / 90 °C / Inert atmosphere

With pyridine; lithium aluminium tetrahydride; oxalyl dichloride; ammonia; pyridine hydrochloride; sodium; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 3.1: |Swern Oxidation / 3.2: |Swern Oxidation / 7.1: |Birch Reduction;

DOI:10.1021/acs.orglett.6b00661

Reference yield:

C31H31NO3 → (-)-koumine (1358-76-5,83705-29-7,119241-69-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: pyridine / tetrahydrofuran; toluene / 2 h / -78 - -40 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.2: 1.5 h / -78 °C / Inert atmosphere

3.1: toluene-4-sulfonic acid / methanol / 8 h / 20 °C / Inert atmosphere

4.1: pyridine; pyridine hydrochloride / 23 h / 100 °C / Inert atmosphere

5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

5.2: 2 h / 0 - 20 °C / Inert atmosphere

6.1: ammonia; sodium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere

7.1: tetrahydrofuran; water / 4.5 h / 0 - 20 °C / Inert atmosphere

8.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

9.1: pyridine / 1 h / 0 - 20 °C / Inert atmosphere

10.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h / 0 - 20 °C / Inert atmosphere

10.2: 3 h / 90 °C / Inert atmosphere

With pyridine; lithium aluminium tetrahydride; oxalyl dichloride; ammonia; pyridine hydrochloride; sodium; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 2.1: |Swern Oxidation / 2.2: |Swern Oxidation / 6.1: |Birch Reduction;

DOI:10.1021/acs.orglett.6b00661

upstream raw materials:

C₂₂H₂₆N₂O₃

18-hydroxytaberpsychine

18-hydroxy-11-demethoxygardnerine

18-hydroxygardnutine

Downstream raw materials:

koumine N-oxide

C₂₀H₂₂N₂O₂

Refernces

• 1、 Takayama, Hiromitsu,Kitajima, Mariko,Sakai, Shin-ichiro. "BIOMIMETIC SYNTHESIS OF KOUMINE BY THE PALLADIUM-CATALYZED INTRAMOLECULAR COUPLING REACTION OF 18-HYDROXYTABERPSYCHINE (18-HYDROXYANHYDROVOBASINEDIOL)". . p. 325 - 327. Retrieved 2007/10/02.