Pachydictyol A

Base Information

• Chemical Name: Pachydictyol A
• CAS No.: 50299-47-3
• Molecular Formula: C₂₀H₃₂O
• Molecular Weight: 288.473
• DSSTox Substance ID: DTXSID00198299
• Wikidata: Q27149821
• Metabolomics Workbench ID: 124000
• ChEMBL ID: CHEMBL1652216
• Mol file: 50299-47-3.mol

Synonyms:Pachydictyol A;50299-47-3;CHEBI:80771;4-Azulenol, 5-(1,5-dimethyl-4-hexenyl)-1,3a,4,5,6,7,8,8a-octahydro-3-methyl-8-methylene-, (3aS-(3aalpha,4alpha,5alpha(S*),8abeta))-;CHEMBL1652216;SCHEMBL17336020;DTXSID00198299;Q27149821;(3aS,4R,5S,8aR)-5-[(1R)-1,5-dimethylhex-4-enyl]-3-methyl-8-methylene-3a,4,5,6,7,8a-hexahydro-1H-azulen-4-ol;4-Azulenol, 5-[(1R)-1,5-dimethyl-4-hexenyl]-1,3a,4,5,6,7,8,8a-octahydro-3-methyl-8-methylene-, (3aS,4R,5S,8aR)-

Chemical Property of Pachydictyol A

Chemical Property:

• Vapor Pressure: 6.49E-08mmHg at 25°C
• Boiling Point: 396°Cat760mmHg
• Flash Point: 168.6°C
• PSA: 20.23000
• Density: 0.95g/cm³
• LogP: 5.27840
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 288.245315640
• Heavy Atom Count: 21
• Complexity: 439

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC2C1C(C(CCC2=C)C(C)CCC=C(C)C)O
• Isomeric SMILES: CC1=CC[C@@H]2[C@@H]1[C@@H]([C@@H](CCC2=C)[C@H](C)CCC=C(C)C)O

Technology Process of Pachydictyol A

There total 22 articles about Pachydictyol A 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:

dehydropachydictyol A (67310-24-1) → (6R)-6-hydroxydichotoma-3,14-diene-1,17-dial (50299-47-3)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at -77 ℃; for 3h;

DOI:10.1021/ja00536a036

Reference yield:

C24H30N2O6S → (6R)-6-hydroxydichotoma-3,14-diene-1,17-dial (50299-47-3)

Guidance literature:

Multi-step reaction with 12 steps

1: BF₃*OEt₂ / acetone; H₂O / 108 h / Ambient temperature

2: 5percent aq. potassium hydroxide / 1.25 h

3: 3.3 g / pyridine, thionyl chloride / tetrahydrofuran / 0.17 h / -45 °C

4: ethanol / 2 h / 80 °C

5: 1.) catecholborane, 3.) sodium acetate trihydrate

6: 95 percent / lithium aluminium hydride / diethyl ether

7: pyridine / 2 h / -30 °C

8: 0.25 h / -30 °C

9: 1-pentynylcopper / diethyl ether / 1.) -40 - -30 deg C, 2 h, 2.) -20 - -15 deg C, overnight

10: 33 percent / AcOH, H₂O / tetrahydrofuran / 0.75 h / Ambient temperature

11: chromic acid / diethyl ether / 0 °C

12: 23 mg / lithium aluminium hydride / diethyl ether / 3 h / -77 °C

With pyridine; 1-pentynyl copper; potassium hydroxide; lithium aluminium tetrahydride; thionyl chloride; boron trifluoride diethyl etherate; water; sodium acetate; chromic acid; acetic acid; benzo[1,3,2]dioxaborole; In tetrahydrofuran; diethyl ether; ethanol; water; acetone;

DOI:10.1021/ja00536a036

Reference yield:

6-epi-pachydictyol A (67310-23-0) → (6R)-6-hydroxydichotoma-3,14-diene-1,17-dial (50299-47-3)

Guidance literature:

Multi-step reaction with 2 steps

1: chromic acid / diethyl ether / 0 °C

2: 23 mg / lithium aluminium hydride / diethyl ether / 3 h / -77 °C

With lithium aluminium tetrahydride; chromic acid; In diethyl ether;

DOI:10.1021/ja00536a036

upstream raw materials:

dictyol G acetate

dehydropachydictyol A

epoxypachydictiol A

dictyoxide

Downstream raw materials:

9-epi-dictyol B dibenzoate

dictyol B

4-Bromo-benzoic acid (3aR,5R,7S,8R,8aS)-7-((R)-1,5-dimethyl-hex-4-enyl)-8-hydroxy-1-methyl-4-methylene-3,3a,4,5,6,7,8,8a-octahydro-azulen-5-yl ester

Refernces

• 1、 Fattorusso et al.. "". . p. 575. Retrieved 1976.
• 2、 Enoki, Nobuyasu,Tsuzuki, Kazuo,Omura, Satoshi,Ishida, Ryoichi,Matsumoto, Takeshi. "NEW ANTIMICROBIAL DITERPENES, DICTYOL F AND EPIDICTYOL F, FROM THE BROWN ALGA DICTYOTA DICHOTOMA". . p. 1627 - 1630. Retrieved 2007/10/02.