5-Cycloundecene-1-carboxylic acid, 1,5-dimethyl-9-methylene-2-((2-oxo-2H-1-benzopyran-7-yl)oxy)-

Base Information

• Chemical Name: 5-Cycloundecene-1-carboxylic acid, 1,5-dimethyl-9-methylene-2-((2-oxo-2H-1-benzopyran-7-yl)oxy)-
• CAS No.: 21800-49-7
• Molecular Formula: C₂₄H₂₈O₅
• Molecular Weight: 396.483
• Mol file: 21800-49-7.mol

Synonyms:Karatavic acid;Caratavinkovic acid;(+-)-Karatavic acid;BRN 4579293;5-Cycloundecene-1-carboxylic acid, 1,5-dimethyl-9-methylene-2-((2-oxo-2H-1-benzopyran-7-yl)oxy)-;(1alpha,2beta,6beta)-1,3-Dimethyl-6-(1-methylethyenyl)-2-(((2-oxo-2H-1-benzopyran-7-yl)oxy)methyl)-3-cyclohexene-1-propanoic acid;1,3-Dimethyl-6-(1-methylethenyl)-2-(((2-oxo-2H-1-benzopyran-7-yl)oxy)methyl)-3-cyclohexene-1-propanoic acid (1alpha,2beta,6beta)-;3-Cyclohexene-1-propanoic acid, 1,3-dimethyl-6-(1-methylethenyl)-2-(((2-oxo-2H-1-benzopyran-7-yl)oxy)methyl)-, (1alpha,2beta,6beta)-;LS-58868;5-18-01-00407 (Beilstein Handbook Reference)

Chemical Property of 5-Cycloundecene-1-carboxylic acid, 1,5-dimethyl-9-methylene-2-((2-oxo-2H-1-benzopyran-7-yl)oxy)-

Chemical Property:

• Vapor Pressure: 1.4E-14mmHg at 25°C
• Boiling Point: 586.1°Cat760mmHg
• Flash Point: 199.6°C
• PSA: 76.74000
• Density: 1.19g/cm³
• LogP: 5.20140
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 396.19367399
• Heavy Atom Count: 29
• Complexity: 706

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s): A poison.
• Hazard Codes: A poison.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCCC(=C)CCC(C(CC1)OC2=CC3=C(C=C2)C=CC(=O)O3)(C)C(=O)O
• Isomeric SMILES: C/C/1=C/CCC(=C)CCC(C(CC1)OC2=CC3=C(C=C2)C=CC(=O)O3)(C)C(=O)O

Technology Process of 5-Cycloundecene-1-carboxylic acid, 1,5-dimethyl-9-methylene-2-((2-oxo-2H-1-benzopyran-7-yl)oxy)-

There total 5 articles about 5-Cycloundecene-1-carboxylic acid, 1,5-dimethyl-9-methylene-2-((2-oxo-2H-1-benzopyran-7-yl)oxy)- 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: 93.0%

3-[(1R,2R,6R)-6-Isopropenyl-1,3-dimethyl-2-(2-oxo-2H-chromen-7-yloxymethyl)-cyclohex-3-enyl]-propionitrile (90396-66-0) → (+/-)-karatavic acid (21800-49-7,90457-94-6)

Guidance literature:

With potassium hydroxide; In ethanol; for 5h; Heating;

DOI:10.1016/S0040-4039(00)99905-2

Reference yield:

7-hydroxy-2H-chromen-2-one (93-35-6) → (+/-)-karatavic acid (21800-49-7,90457-94-6)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydride, tetrabutylammonium bromide / dimethylformamide

3: 94 percent / hydroxylamine hydrochloride / pyridine; ethanol / 2 h / Heating

4: 29 percent / p-toluenesulfonyl chloride / pyridine / Heating

5: 93 percent / KOH / ethanol / 5 h / Heating

With potassium hydroxide; hydroxylamine hydrochloride; tetrabutylammomium bromide; sodium hydride; p-toluenesulfonyl chloride; In pyridine; ethanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)99905-2

Reference yield:

umbelliprenine (23838-17-7) → (+/-)-karatavic acid (21800-49-7,90457-94-6)

Guidance literature:

Multi-step reaction with 4 steps

2: 94 percent / hydroxylamine hydrochloride / pyridine; ethanol / 2 h / Heating

3: 29 percent / p-toluenesulfonyl chloride / pyridine / Heating

4: 93 percent / KOH / ethanol / 5 h / Heating

With potassium hydroxide; hydroxylamine hydrochloride; p-toluenesulfonyl chloride; In pyridine; ethanol;

DOI:10.1016/S0040-4039(00)99905-2

upstream raw materials:

3-[(1R,2R,6R)-6-Isopropenyl-1,3-dimethyl-2-(2-oxo-2H-chromen-7-yloxymethyl)-cyclohex-3-enyl]-propionitrile

7-hydroxy-2H-chromen-2-one

umbelliprenine

conferone

Downstream raw materials:

3-[(1R,2R,6R)-6-Isopropenyl-1,3-dimethyl-2-(2-oxo-2H-chromen-7-yloxymethyl)-cyclohex-3-enyl]-propionic acid methyl ester

Refernces