Taspine

Base Information

• Chemical Name: Taspine
• CAS No.: 602-07-3
• Molecular Formula: C₂₀H₁₉NO₆
• Molecular Weight: 369.374
• NSC Number: 688259
• UNII: V53XN9L07O
• DSSTox Substance ID: DTXSID60975624
• Nikkaji Number: J409.533B
• Wikipedia: Taspine
• Wikidata: Q5486808
• Pharos Ligand ID: K8ANR84SN82R
• Metabolomics Workbench ID: 137390
• ChEMBL ID: CHEMBL470867
• Mol file: 602-07-3.mol

Synonyms:taspine;taspine sulfate (1:1);thaspine

Chemical Property of Taspine

Chemical Property:

• Vapor Pressure: 5.5E-13mmHg at 25°C
• Melting Point: >300°C (dec.)
• Boiling Point: 569.6°C at 760 mmHg
• PKA: 7.85±0.28(Predicted)
• Flash Point: 298.3°C
• PSA: 82.12000
• Density: 1.35g/cm³
• LogP: 2.61170
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 369.12123733
• Heavy Atom Count: 27
• Complexity: 595

Purity/Quality:

98%min ^*data from raw suppliers

Taspine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCC1=CC(=C2C3=C1C(=O)OC4=C(C=CC(=C34)C(=O)O2)OC)OC
• Uses: It is an alkaloid isolated from Radix et Rhizoma Leonticis. It shows various pharmaceutical properties: bacteriostatic, wound healing, cytotoxicity, immunosuppression, acetilcholinesterase inhibition, and inhibition of the activity of tumor angiogenesis.

Technology Process of Taspine

There total 10 articles about Taspine 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: 77.0%

dimethyl amine (124-40-3) + 3,8-dimethoxy-1-(2-oxoethyl)[1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione (216374-60-6) → taspine (602-07-3)

Guidance literature:

dimethyl amine; 3,8-dimethoxy-1-(2-oxoethyl)[1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione; In tetrahydrofuran; dichloromethane; at 20 ℃; for 0.333333h; Inert atmosphere;

With sodium tris(acetoxy)borohydride; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1055/s-0029-1217393

Reference yield:

Isovanillic acid (645-08-9,74309-78-7) → taspine (602-07-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) dicyclohexylcarbodiimide, N-hydroxysuccinimide / 1) THF, acetonitrile, rt, 12 h; 2) THF, CH₃CM, reflux, 2 h

2: 1.) NaOH, Adogen 464 / 1) CH₂Cl₂, water, rt, 30 min; 2) CH₂Cl₂, water, 0 deg C, 1 h

3: 1.) n-BuLi, 2.) I₂ / 1) THF, pentane, -60 deg C, 2 h; 2) THF, pentane, -60 deg C --> rt, 1 h

4: 66 percent / copper bronze / dimethylformamide / 3 h / Heating

5: 1.) n-BuLi, 2.) I₂ / 1) THF, pentane, -60 deg C, 2 h; 2) THF, pentane, -60 deg C --> rt, 1 h

6: 82 percent / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / dioxane / 14 h / Heating

7: 1.) O₃, 1.) dimethyl sulfide / 1) 1,2-dichloroethane, -78 deg C; 2) 1,2-dichloroethane, -78 deg C, 1 h, 0 deg C, 1 h, rt, 1 h

8: 75 percent / sodium triacetoxyborohydride / 1,2-dichloro-ethane / 0.17 h / Ambient temperature

With sodium hydroxide; 1-hydroxy-pyrrolidine-2,5-dione; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; adogen 464; dimethylsulfide; iodine; sodium tris(acetoxy)borohydride; copper; ozone; dicyclohexyl-carbodiimide; In 1,4-dioxane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jo981099j

Reference yield:

3-Hydroxy-4-methoxy-N-propyl-benzamide (216374-54-8) → taspine (602-07-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaOH, Adogen 464 / 1) CH₂Cl₂, water, rt, 30 min; 2) CH₂Cl₂, water, 0 deg C, 1 h

2: 1.) n-BuLi, 2.) I₂ / 1) THF, pentane, -60 deg C, 2 h; 2) THF, pentane, -60 deg C --> rt, 1 h

3: 66 percent / copper bronze / dimethylformamide / 3 h / Heating

4: 1.) n-BuLi, 2.) I₂ / 1) THF, pentane, -60 deg C, 2 h; 2) THF, pentane, -60 deg C --> rt, 1 h

5: 82 percent / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / dioxane / 14 h / Heating

6: 1.) O₃, 1.) dimethyl sulfide / 1) 1,2-dichloroethane, -78 deg C; 2) 1,2-dichloroethane, -78 deg C, 1 h, 0 deg C, 1 h, rt, 1 h

7: 75 percent / sodium triacetoxyborohydride / 1,2-dichloro-ethane / 0.17 h / Ambient temperature

With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; adogen 464; dimethylsulfide; iodine; sodium tris(acetoxy)borohydride; copper; ozone; In 1,4-dioxane; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jo981099j

upstream raw materials:

dimethyl amine

3,8-dimethoxy-1-(2-oxoethyl)[1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione

Isovanillic acid

3-Hydroxy-4-methoxy-N-propyl-benzamide

Downstream raw materials:

Taspin-hydrochlorid

Refernces

• 1、 Cheng, Bin,Zhang, Sanqi,Zhu, Liyong,Zhang, Jie,Li, Qiang,Shan, Ailin,He, Langchong. "Facile and efficient total synthesis of taspine". experimental part. p. 2501 - 2504. Retrieved 2009/12/08.