(±)-thalictricavine

Base Information

• Chemical Name: (±)-thalictricavine
• CAS No.: 38969-46-9
• Molecular Formula: C₂₁H₂₃NO₄
• Molecular Weight: 353.418
• Mol file: 38969-46-9.mol

Synonyms:(±)-thalictricavine

Chemical Property of (±)-thalictricavine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (±)-thalictricavine

There total 7 articles about (±)-thalictricavine 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: 86.0%

dehydrothalictricavine iodide (2220-12-4) → Thalictricavin (478-12-6,13166-15-9,24314-67-8,24314-68-9,29550-24-1,38969-46-9,61116-97-0,107538-90-9)

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 2h; Heating;

Reference yield:

2-(2-bromo-4,5-dimethoxyphenylphenyl)ethan-1-amine (63375-81-5) → (±)-thalictricavine (38969-46-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: CH₂Cl₂ / 24 h / 20 °C

2.1: LiAlH₄ / tetrahydrofuran / 2 h / 20 °C

3.1: Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

4.1: SnCl₄ / CH₂Cl₂ / 1 h / 0 °C

5.1: LDA / tetrahydrofuran / 1 h / -78 °C

5.2: 80 percent / tetrahydrofuran / 1 h / 20 °C

6.1: 88 percent / Raney Ni / ethanol / 2 h / Heating

7.1: POCl₃; K₂CO₃ / acetonitrile / 2 h / 60 °C

8.1: NaBH₄ / methanol / 1 h / 20 °C

9.1: NaBH₄ / methanol / 1 h / 20 °C

With sodium tetrahydroborate; lithium aluminium tetrahydride; tin(IV) chloride; nickel; potassium carbonate; triethylamine; lithium diisopropyl amide; trichlorophosphate; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetonitrile; 1.1: Condensation / 2.1: Reduction / 3.1: Acylation / 4.1: Cyclization / 5.1: Metallation / 5.2: Methylation / 6.1: desulfurization; debromination / 7.1: Bischler-Napieralski reaction / 8.1: Reduction / 9.1: Reduction;

DOI:10.1248/cpb.48.399

Reference yield:

7,8-dihydroberberine (483-15-8) → (±)-thalictricavine (38969-46-9)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOAc / acetic acid

2: NaBH₄ / methanol

With sodium tetrahydroborate; sodium acetate; In methanol; acetic acid; 1: Methylation / 2: Reduction;

DOI:10.1016/S0040-4020(00)00945-5

upstream raw materials:

formaldehyd

7,8-dihydroberberine

methyl iodide

2-(2-bromo-4,5-dimethoxyphenylphenyl)ethan-1-amine

Downstream raw materials:

13-methylberberine

Refernces

• 1、 Hanaoka, Miyoji,Hirasawa, Taeko,Cho, Won Jea,Yasuda, Shingo. "Convenient synthesis of 2,3,9,10-tetraoxygenated protoberberine alkaloids and their 13-methyl alkaloids". . p. 399 - 404. Retrieved 2007/10/03.