8-hydroxy-2-methyl-1-[(E)-non-3-enyl]-4a,7,8,9,9a,9b-hexahydro-3H-cyclopenta[f]chromen-5-one

Base Information

• Chemical Name: 8-hydroxy-2-methyl-1-[(E)-non-3-enyl]-4a,7,8,9,9a,9b-hexahydro-3H-cyclopenta[f]chromen-5-one
• CAS No.: 173485-70-6
• Molecular Formula: C₂₂H₃₂O₃
• Molecular Weight: 344.494
• Mol file: 173485-70-6.mol

Synonyms:8-hydroxy-2-methyl-1-[(E)-non-3-enyl]-4a,7,8,9,9a,9b-hexahydro-3H-cyclopenta[f]chromen-5-one;UNII-JAQ4MH3LR5

Chemical Property of 8-hydroxy-2-methyl-1-[(E)-non-3-enyl]-4a,7,8,9,9a,9b-hexahydro-3H-cyclopenta[f]chromen-5-one

Chemical Property:

• Vapor Pressure: 3.67E-12mmHg at 25°C
• Boiling Point: 509.3°Cat760mmHg
• Flash Point: 173.2°C
• PSA: 46.53000
• Density: 1.09g/cm³
• LogP: 4.51300
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 344.23514488
• Heavy Atom Count: 25
• Complexity: 584

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCC=CCCC1=C(COC2C1C3CC(CC3=CC2=O)O)C
• Isomeric SMILES: CCCCC/C=C/CCC1=C(COC2C1C3CC(CC3=CC2=O)O)C

Technology Process of 8-hydroxy-2-methyl-1-[(E)-non-3-enyl]-4a,7,8,9,9a,9b-hexahydro-3H-cyclopenta[f]chromen-5-one

There total 25 articles about 8-hydroxy-2-methyl-1-[(E)-non-3-enyl]-4a,7,8,9,9a,9b-hexahydro-3H-cyclopenta[f]chromen-5-one 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: 100.0%

8-(tert-butyldimethylsilyloxy)-2-methyl-3-((E)-non-1-enyl)-4a,7,8,9,9a,9b-hexahydrocyclopenta[f]chromen-5(3H)-one → (+/-)-penostatin B (173485-70-6)

Guidance literature:

With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 4.17h; Inert atmosphere; Cooling with ice;

DOI:10.1021/ol203021c

Reference yield:

C35H56O3Si → (+/-)-penostatin B (173485-70-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: magnesium bromide ethyl etherate / tetrahydrofuran / 0.05 h / -78 °C

2.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 8 h / 20 °C / Molecular sieve

3.1: lithium diisopropyl amide / tetrahydrofuran / 0.25 h / -78 - 0 °C

3.2: 0.5 h / 0 °C

4.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 4.17 h / 20 °C / Inert atmosphere; Cooling with ice

With pyridine; tetrapropylammonium perruthennate; pyridine hydrogenfluoride; magnesium bromide ethyl etherate; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; 3.1: Ito-Saegusa oxidation / 3.2: Ito-Saegusa oxidation;

DOI:10.1021/ol203021c

Reference yield:

C28H48O3Si → (+/-)-penostatin B (173485-70-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 0.25 h / -78 - 0 °C

1.2: 0.5 h / 0 °C

2.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 4.17 h / 20 °C / Inert atmosphere; Cooling with ice

With pyridine; pyridine hydrogenfluoride; lithium diisopropyl amide; In tetrahydrofuran; 1.1: Ito-Saegusa oxidation / 1.2: Ito-Saegusa oxidation;

DOI:10.1021/ol203021c

Refernces

• 1、 Wang, Jian,Márquez-Cadena, Miguel Adrián,Tong, Rongbiao. "Asymmetric Total Syntheses of (+)-Penostatins A and C". . p. 5074 - 5078. Retrieved 2020.