(R)-(+)-Nicoumalone

Base Information

• Chemical Name: (R)-(+)-Nicoumalone
• CAS No.: 66556-77-2
• Molecular Formula: C₁₉H₁₅NO₆
• Molecular Weight: 353.331

Synonyms:4-hydroxy-3-[(1R)-1-(4-nitrophenyl)-3-oxobutyl]chromen-2-one;(R)-Acenocoumarol;

Chemical Property of (R)-(+)-Nicoumalone

Chemical Property:

• Vapor Pressure: 8.54E-13mmHg at 25°C
• Boiling Point: 546.9°Cat760mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 284.6°C
• PSA: 113.33000
• Density: 1.427g/cm³
• LogP: 4.04100

Purity/Quality:

99% ^*data from raw suppliers

(R)-Acenocoumarol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: R-Enantiomer of

Technology Process of (R)-(+)-Nicoumalone

There total 8 articles about (R)-(+)-Nicoumalone 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: 98.0%

4-(p-nitrophenyl)-3-butene-2-one (946-49-6,3490-37-7,30625-98-0) + 4-hydroxydihydrocoumarin → (+)-Acenocoumarol (152-72-7,66556-78-3,70897-81-3,66556-77-2)

Guidance literature:

With (S,S)-N-diphenylphosphinyl-1,2-diphenylethane-1,2-diamine; p-Toluic acid; In toluene; at 20 ℃; for 72h; enantioselective reaction;

DOI:10.1039/c2ob26334c

Reference yield:

4-(p-nitrophenyl)-3-butene-2-one (946-49-6,3490-37-7,30625-98-0) + 4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) → (+)-Acenocoumarol (152-72-7,66556-78-3,70897-81-3,66556-77-2) + (-)-Acenocoumarol (152-72-7,66556-77-2,70897-81-3,66556-78-3)

Guidance literature:

With C₃₆H₃₀N₂; trifluoroacetic acid; In dichloromethane; at 0 ℃; for 41h; optical yield given as %ee; enantioselective reaction;

DOI:10.5012/bkcs.2012.33.6.1825

Reference yield:

4-(p-nitrophenyl)-3-butene-2-one (946-49-6,3490-37-7,30625-98-0) + 4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) → (+)-Acenocoumarol (152-72-7,66556-78-3,70897-81-3,66556-77-2) + (-)-Acenocoumarol (152-72-7,66556-77-2,70897-81-3,66556-78-3)

Guidance literature:

With C₃₆H₃₀N₂; trifluoroacetic acid; In dichloromethane; at 0 ℃; for 41h; optical yield given as %ee; enantioselective reaction;

DOI:10.5012/bkcs.2012.33.6.1825

upstream raw materials:

4-hydroxy[1]benzopyran-2-one

(E)-4-(4-nitrophenyl)-3-buten-2-one

4-(p-nitrophenyl)-3-butene-2-one

4-nitrobenzaldehdye

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