Avocadyne

Base Information

• Chemical Name: Avocadyne
• CAS No.: 24607-05-4
• Molecular Formula: C₁₇H₃₂O₃
• Molecular Weight: 284.439
• DSSTox Substance ID: DTXSID20947504
• Nikkaji Number: J19.337B
• Wikidata: Q82925306
• Metabolomics Workbench ID: 46956
• ChEMBL ID: CHEMBL443127
• Mol file: 24607-05-4.mol

Synonyms:avocadyne

Chemical Property of Avocadyne

Chemical Property:

• Vapor Pressure: 1.04E-09mmHg at 25°C
• Boiling Point: 443°C at 760 mmHg
• Flash Point: 198.6°C
• PSA: 60.69000
• Density: 0.993g/cm³
• LogP: 3.01490
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 284.23514488
• Heavy Atom Count: 20
• Complexity: 244

Purity/Quality:

99%, ^*data from raw suppliers

Avocadyne ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C#CCCCCCCCCCCCC(CC(CO)O)O
• Uses: Avocadyne is an anti fungal compound found in immature avocado peel and seeds.

Technology Process of Avocadyne

There total 25 articles about Avocadyne 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%

C19H34O4 → (2R,4R)-1,2,4-trihydroxyheptadeca-16-yne (24607-05-4,34524-38-4,129099-94-1,129099-95-2,129099-96-3,129099-93-0)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 - 20 ℃; for 3.5h; stereoselective reaction;

DOI:10.1021/acs.joc.9b02391

Reference yield: 71.0%

(R)-ethyl 2-hydroxy-4-oxoheptadec-16-ynoate → avocadyne (24607-05-4,34524-38-4) + (2R,4S)-heptadec-16-yne-1,2,4-triol (129099-94-1)

Guidance literature:

(R)-ethyl 2-hydroxy-4-oxoheptadec-16-ynoate; With acetic acid; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; acetonitrile; at -30 - -20 ℃; for 18h;

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 - 25 ℃; for 3.5h;

DOI:10.1021/acs.joc.9b02391

Reference yield:

2-[(11-bromoundecyl)oxy]tetrahydro-2H-pyran (52056-69-6) → (2R,4R)-1,2,4-trihydroxyheptadeca-16-yne (24607-05-4,34524-38-4,129099-94-1,129099-95-2,129099-96-3,129099-93-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 80 percent / liq. NH₃, HMPA / 1) -70 deg C, 3h, 2) RT, overnight

2: 1) n-BuLi / 1a) Et₂O, cyclohexane, 0 deg C, 1h, 1b) RT, 30 min, 2a) 1h, 0 deg C, 2b) 1h, RT

3: 90 percent / p-TsOH / methanol / Ambient temperature

4: NEt₃ / CH₂Cl₂ / 1) 0 deg C, 30 min, 2) RT, 2h

5: 73 percent / LiBr / tetrahydrofuran / 2 h / Heating

6: 1) Mg / 1) Et₂O, 2) Et₂O, RT, overnight

7: 90 percent / Bu₄NF / tetrahydrofuran / 0.17 h / Ambient temperature

8: p-TsOH / methanol / 10 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; tetrabutyl ammonium fluoride; ammonia; toluene-4-sulfonic acid; magnesium; triethylamine; lithium bromide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/0031-9422(90)83005-L

upstream raw materials:

avocadyne acetate

1-iodo-n-undecane

(2R,4RS) 1,2-acetonide-16-heptadecyn-1,2,4-triol

2-[(11-bromoundecyl)oxy]tetrahydro-2H-pyran

Downstream raw materials:

1,2,4-trihydroxy-heptadeca-16-ene

avocadene

Refernces

• 1、 Cunha, Vitor L. S.,Liu, Xiaofan,Lowary, Todd L.,O'Doherty, George A.. "De Novo Asymmetric Synthesis of Avocadyne, Avocadene, and Avocadane Stereoisomers". . p. 15718 - 15725. Retrieved 2019/11/19.