11,16-Dihydroxyoctadeca-9,17-diene-12,14-diyn-1-yl acetate

Base Information

• Chemical Name: 11,16-Dihydroxyoctadeca-9,17-diene-12,14-diyn-1-yl acetate
• CAS No.: 213905-35-2
• Molecular Formula: C20H28O4
• Molecular Weight: 332.43400
• DSSTox Substance ID: DTXSID80702499
• Wikidata: Q72434379,Q105297904
• Mol file: 213905-35-2.mol

Synonyms:213905-35-2;1-Acetoxy-9,17-octadecadiene-12,14-diyne-11,16-diol;9,17-octadecadiene-12,14-diyne-1,11,16-triol 1-acetate;DTXSID80702499;11,16-Dihydroxyoctadeca-9,17-diene-12,14-diyn-1-yl acetate

Chemical Property of 11,16-Dihydroxyoctadeca-9,17-diene-12,14-diyn-1-yl acetate

Chemical Property:

• Boiling Point: 494.2±45.0 °C(Predicted)
• PKA: 11.63±0.20(Predicted)
• PSA: 66.76000
• Density: 1.061±0.06 g/cm3(Predicted)
• LogP: 2.75100
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 13
• Exact Mass: 332.19875937
• Heavy Atom Count: 24
• Complexity: 521

Purity/Quality:

99.5% ^*data from raw suppliers

11,16-Dihydroxyoctadeca-9,17-dien-12,14-diyn-1-ylacetate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCCCCCCCCC=CC(C#CC#CC(C=C)O)O

Technology Process of 11,16-Dihydroxyoctadeca-9,17-diene-12,14-diyn-1-yl acetate

There total 7 articles about 11,16-Dihydroxyoctadeca-9,17-diene-12,14-diyn-1-yl acetate 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:

(S,Z)-11-hydroxytridec-9-en-12-yn-1-yl acetate + (R)-5-bromo-1-penten-4-yn-3-ol (72800-75-0) → (11S,16R,Z)-11,16-dihydroxyoctadeca-9,17-dien-12,14-diyn-1-yl acetate (213905-35-2)

Guidance literature:

With hydroxylamine hydrochloride; N-butylamine; copper(l) chloride; In methanol; dichloromethane; at 0 ℃; Darkness; Inert atmosphere;

DOI:10.1002/anie.201302538

Reference yield:

(S,Z)-11-hydroxytridec-9-en-12-yn-1-yl acetate + (+)-5-bromopent-1-en-4-yne-3-ol (488791-21-5) → (11S,16S,Z)-11,16-dihydroxyoctadeca-9,17-dien-12,14-diyn-1-yl acetate (213905-35-2)

Guidance literature:

With hydroxylamine hydrochloride; N-butylamine; copper(l) chloride; In methanol; dichloromethane; at 0 ℃; for 3h; Darkness; Inert atmosphere;

DOI:10.1002/anie.201302538

Reference yield:

(S,Z)-11-((tert-butyldimethylsilyl)oxy)-13-(triisopropylsilyl)tridec-9-en-12-yn-1-yl acetate → (11S,16R,Z)-11,16-dihydroxyoctadeca-9,17-dien-12,14-diyn-1-yl acetate (213905-35-2)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 22 °C / Inert atmosphere; Glovebox

2: copper(l) chloride; hydroxylamine hydrochloride; N-butylamine / dichloromethane; methanol / 0 °C / Darkness; Inert atmosphere

With hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; N-butylamine; copper(l) chloride; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/anie.201302538

upstream raw materials:

(+)-5-bromopent-1-en-4-yne-3-ol

3-hydroxy-4-penten-1-ynyltrimethylsilane

(S)‐5‐(trimethylsilyl)pent‐1‐en‐4‐yn‐3‐ol

(R)-5-bromo-1-penten-4-yn-3-ol

Downstream raw materials:

oplopantriol A