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
• General Description: Taspine, also known as Thaspine, NSC 688259, Taspin, or Taspine, is an alkaloid characterized by an unusual diphenylic skeleton. Its synthesis presents challenges due to asymmetric diphenylic coupling and steric hindrance, prompting the development of simplified model compounds for study. These models, such as methyl-substituted derivatives and symmetric lactones, exhibit distinct chemical properties, including high insolubility in most solvents, and provide insights into the structural and synthetic complexities of taspine.

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

Synthesis of models related to taspine

10.1080/00397919108019768

The research details the synthesis of diphenylic compounds related to the alkaloid taspine, an alkaloid with an unusual diphenylic skeleton that had not been previously synthesized. The study aimed to address the challenges in taspine synthesis, such as asymmetric diphenylic coupling and steric hindrance, by synthesizing simplified models. The researchers reported the synthesis of compound 2, which carries a methyl group instead of the 2-(N-dimethylamino)-ethyl group present in taspine, and the symmetric lactone 32, obtained as a by-product. Key chemicals used in the process included 2-bromo-4-methoxy-3-methoxycarbonyloxy-6-methylbenzaldehyde (S3), 3-benzyloxy-2-bromo-4-methoxybenzaldehyde (6), and various other derivatives and reagents such as copper bronze for the Ullmann reaction, Jones' reagent for oxidation, and hydrogenolysis for the removal of benzyl groups. The final products, dilactones 2 and 3, were obtained in high yields and were found to be insoluble in most solvents, with properties differing from those previously reported for similar structures.

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 602-07-3 taspine

Send

Send

Metric Ton KG G Pound L ML

Send

Send