CID 16667702

Base Information

• Chemical Name: CID 16667702
• CAS No.: 2182-14-1
• Molecular Formula: C25H32N2O6
• Molecular Weight: 456.539
• Hs Code.: 29339900
• European Community (EC) Number: 218-558-0
• Metabolomics Workbench ID: 50479
• NCI Thesaurus Code: C1273
• Wikipedia: Vindoline
• Mol file: 2182-14-1.mol

Synonyms:vindoline;vindoline, citrate, (2beta,3beta,4beta,5alpha,12beta,19alpha)-isomer;vindoline, monohydrochloride, (2beta,3beta,4beta,5alpha,12beta,19alpha)-isomer

Chemical Property of CID 16667702

Chemical Property:

• Appearance/Colour: Off-white solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 163-165 °C
• Refractive Index: 1.626
• Boiling Point: 569.8 °C at 760 mmHg
• PKA: 5.5 in 66% DMF (Moza, Trojánek)
• Flash Point: 298.4 °C
• PSA: 88.54000
• Density: 1.33 g/cm³
• LogP: 1.64420
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 456.22603674
• Heavy Atom Count: 33
• Complexity: 864

Purity/Quality:

99%, ^*data from raw suppliers

Vindoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 68
• Safety Statements: 36/37-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC12C=CCN3C1C4(CC3)C(C(C2OC(=O)C)(C(=O)OC)O)N(C5=C4C=CC(=C5)OC)C
• Isomeric SMILES: CC[C@@]12C=CCN3[C@@H]1[C@]4(CC3)C([C@]([C@@H]2OC(=O)C)(C(=O)OC)O)N(C5=C4C=CC(=C5)OC)C
• Uses: A novel antitumor agent Vindoline is a novel antitumor agent.

Technology Process of CID 16667702

There total 157 articles about CID 16667702 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: 91.0%

C25H30N2O7 → vindoline (2182-14-1)

Guidance literature:

C₂₅H₃₀N₂O₇; With 2,6-di-tert-butyl-pyridine; methyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

With sodium tetrahydroborate; In methanol; at 20 ℃; for 0.25h;

DOI:10.1016/j.tet.2018.11.046

Reference yield: 91.0%

acetic anhydride (108-24-7) + (3aR,3a1R,4R,5S,5aR,10bR)-methyl 3a-ethyl-4,5-dihydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1H-indolizino-[8,1-cd]carbazole-5-carboxylate (3633-92-9) → vindoline (2182-14-1)

Guidance literature:

With sodium acetate; at 20 ℃; for 4h;

Reference yield: 75.0%

(2S,3aR,4R,5S,5aR,10bR,12bR)-4-Acetoxy-3a-ethyl-2,5-dihydroxy-8-methoxy-6-methyl-2,3,3a,4,5,5a,6,11,12,12b-decahydro-1H-6,12a-diaza-indeno[7,1-cd]fluorene-5-carboxylic acid methyl ester (867214-27-5) → vindoline (2182-14-1)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1021/ol051975x

upstream raw materials:

tryptamine hydochloride

S-Adenosyl-L-methionine

acetic anhydride

(3aR,3a¹R,4R,5S,5aR,10bR)-methyl 3a-ethyl-4,5-dihydroxy-8-methoxy-6-methyl-3a,3a¹,4,5,5a,6,11,12-octahydro-1H-indolizino-[8,1-cd]carbazole-5-carboxylate

Refernces

• 1、 Rasoanaivo et al.. "-". . p. 641,642, 644. Retrieved 1979.
• 2、 Chen, Wen,Tian, Hongchang,Tan, Wenyun,Liu, Xiaotong,Yang, Xiaodong,Zhang, Hongbin. "Total synthesis of (?)-vindoline". . p. 1751 - 1759. Retrieved 2019.
• 3、 Kato, Daisuke,Sasaki, Yoshikazu,Boger, Dale L.. "Asymmetric total synthesis of vindoline". supporting information; experimental part. p. 3685 - 3687. Retrieved 2010/05/15.