8,12-Heptadecatriene-4,6-diyne-1,14-diol, (E,E,E)-(-)-

Base Information

• Chemical Name: 8,12-Heptadecatriene-4,6-diyne-1,14-diol, (E,E,E)-(-)-
• CAS No.: 505-75-9
• Molecular Formula: C17H22 O2
• Molecular Weight: 258.36
• Hs Code.: 2905399090
• ChEMBL ID: CHEMBL453245
• Metabolomics Workbench ID: 135182
• Nikkaji Number: J6.227H
• NSC Number: 606489
• Mol file: 505-75-9.mol

Synonyms:NSC-606489;SCHEMBL166718;CHEMBL453245;NSC606489;8,12-Heptadecatriene-4,6-diyne-1,14-diol, (E,E,E)-(-)-

Chemical Property of 8,12-Heptadecatriene-4,6-diyne-1,14-diol, (E,E,E)-(-)-

Chemical Property:

• Vapor Pressure: 1.08E-10mmHg at 25°C
• Melting Point: 54°
• Refractive Index: 1.4770 (estimate)
• Boiling Point: 467.2°Cat760mmHg
• PKA: 14.07±0.20(Predicted)
• Flash Point: 218.3°C
• PSA: 40.46000
• Density: 1.025g/cm³
• LogP: 2.59530
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 8
• Exact Mass: 258.161979940
• Heavy Atom Count: 19
• Complexity: 429

Purity/Quality:

99% ^*data from raw suppliers

CICUTOXIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC(C=CC=CC=CC#CC#CCCCO)O
• Isomeric SMILES: CCCC(/C=C/C=C/C=C/C#CC#CCCCO)O

Technology Process of 8,12-Heptadecatriene-4,6-diyne-1,14-diol, (E,E,E)-(-)-

There total 23 articles about 8,12-Heptadecatriene-4,6-diyne-1,14-diol, (E,E,E)-(-)- 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: 61.0%

(4R,5E,7E,9E)‐17‐((tetrahydro‐2H‐pyran‐2‐yl)oxy)heptadeca‐5,7,9‐trien‐11,13‐diyn‐4‐ol (1150616-77-5) → Cicutotoxin (505-75-9)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/ejoc.200801172

Reference yield:

7-bromohepta-4,6-diyn-1-ol (1001587-76-3) + (4R,5E,7E,9E)-10-(tributylstannyl)deca-5,7,9-trien-4-ol (1265526-17-7) → Cicutotoxin (505-75-9)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; potassium fluoride; copper(l) iodide; triphenyl-arsane; 2,6-di-tert-butyl-4-methyl-phenol; In 1-methyl-pyrrolidin-2-one; at 45 ℃; for 3.5h; Inert atmosphere;

DOI:10.1002/ejoc.201001231

Reference yield:

7-iodohepta-4,6-diyn-1-ol (1265526-19-9) + (4R,5E,7E,9E)-10-(tributylstannyl)deca-5,7,9-trien-4-ol (1265526-17-7) → Cicutotoxin (505-75-9)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; copper(l) iodide; triphenyl-arsane; 2,6-di-tert-butyl-4-methyl-phenol; In tetrahydrofuran; at 20 - 45 ℃; for 5h; Inert atmosphere;

DOI:10.1002/ejoc.201001231

upstream raw materials:

deca-2t,4t,6t-trienal

(E)-2-Hexenal

2‐(hepta‐4,6‐diyn‐1‐yloxy)tetrahydro‐2H‐pyran

(5E,7E,9E)‐17‐((tetrahydro‐2H‐pyran‐2‐yl)oxy)heptadeca‐5,7,9‐trien‐11,13‐diyn‐4‐ol

Refernces

• 1、 Berger, Martin,Chen, Yong,Bampali, Konstantina,Ernst, Margot,Maulide, Nuno. "Expeditious synthesis of polyacetylenic water hemlock toxins and their effects on the major GABAA receptor isoform". . p. 2008 - 2011. Retrieved 2018/03/01.