OCTAHYDROCOUMARIN

Base Information

• Chemical Name: OCTAHYDROCOUMARIN
• CAS No.: 4430-31-3
• Molecular Formula: C₉H₁₄O₂
• Molecular Weight: 154.209
• European Community (EC) Number: 224-623-4
• DSSTox Substance ID: DTXSID7052105
• Nikkaji Number: J38.333C
• Metabolomics Workbench ID: 47720
• Mol file: 4430-31-3.mol

Synonyms:Coumarin,octahydro- (6CI,8CI);Cyclohexanepropionic acid, 2-hydroxy-, d-lactone (4CI);2-Oxabicyclo[4.4.0]decan-3-one;Cyclohexanepropanoic acid, 2-hydroxy-, d-lactone;

Chemical Property of OCTAHYDROCOUMARIN

Chemical Property:

• Appearance/Colour: Colourless liquid; slight spicy note
• Vapor Pressure: 0.00586mmHg at 25°C
• Refractive Index: n20/D 1.492(lit.)
• Boiling Point: 273.1 °C at 760 mmHg
• Flash Point: 109 °C
• PSA: 26.30000
• Density: 1.056 g/cm³
• LogP: 1.88220
• Storage Temp.: 2-8°C
• Water Solubility.: 39.953g/L at 24℃
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 154.099379685
• Heavy Atom Count: 11
• Complexity: 165

Purity/Quality:

99.9% ^*data from raw suppliers

Octahydro-2H-chromen-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2C(C1)CCC(=O)O2

Technology Process of OCTAHYDROCOUMARIN

There total 54 articles about OCTAHYDROCOUMARIN 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: 99.0%

3-(2-hydroxycyclohexyl)propanenitrile (21197-34-2,370065-38-6) → octahydrocoumarin (4430-31-3,14072-79-8,23201-43-6,121902-57-6,121902-58-7)

Guidance literature:

With sodium hydroxide; In methanol; water; for 48h; Reflux;

DOI:10.1021/acs.joc.8b02025

Reference yield: 91.0%

2-(3-hydroxypropyl)cyclohexan-1-ol (60211-12-3,60211-13-4,53067-09-7) → octahydrocoumarin (4430-31-3,14072-79-8,23201-43-6,121902-57-6,121902-58-7)

Guidance literature:

With [RuCl₂(PPh₃)₂(2-PyCH₂1,3,5-triaza-7-phosphadamantane)].Br; potassium hydroxide; In water; for 48h; Reagent/catalyst; Schlenk technique; Reflux; Inert atmosphere; Green chemistry;

DOI:10.1055/s-0037-1612247

Reference yield: 88.0%

octahydrobenzofuran-2-carbaldehyde → trans-octahydro-1-benzopyran-2-one (4430-31-3,14072-79-8,23201-43-6,121902-57-6,121902-58-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/ol8029005

upstream raw materials:

ethyl 3-(cyclohex-1-en-1-yl)propionate

3-(2-oxocyclohexyl)propionic acid

coumarin

methyl cyclohexane

Downstream raw materials:

2-(3-hydroxypropyl)cyclohexan-1-ol

3-(2trans-Hydroxy-cyclohexyl)-propionsaeure

Sodium; (1S,6R)-6-hydroxymethyl-cyclohex-3-enecarboxylate

Octahydro-chromen-2-one

Refernces

• 1、 Bhatia, Anita,Kannan, Muthukumar,Muthaiah, Senthilkumar. "Ruthenium-Promoted Acceptorless and Oxidant-Free Lactone Synthesis in Aqueous Medium". supporting information. p. 721 - 725. Retrieved 2019/03/26.
• 2、 Parent, Jean-Fran?ois,Deslongchamps, Pierre. "Bent bonds (τ) and the antiperiplanar hypothesis, and the reactivity at the anomeric center in pyranosides". . p. 11183 - 11198. Retrieved 2016/12/09.