(S)-(-)-Nicoumalone

Base Information

• Chemical Name: (S)-(-)-Nicoumalone
• CAS No.: 66556-78-3
• Molecular Formula: C₁₉H₁₅NO₆
• Molecular Weight: 353.331

Synonyms:2H-1-Benzopyran-2-one,4-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-, (S)-;(-)-3-(a-Acetonyl-4-nitrobenzyl)-4-hydroxycoumarin;(-)-Acenocoumarin;(-)-Acenocoumarol;(S)-(-)-Nicoumalone;(S)-Acenocoumarol;(S)-Nicoumalone;S-(-)-Acenocoumarol;

Chemical Property of (S)-(-)-Nicoumalone

Chemical Property:

• Vapor Pressure: 8.54E-13mmHg at 25°C
• Refractive Index: 1.656
• Boiling Point: 546.9 °C at 760 mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 284.6 °C
• PSA: 113.33000
• Density: 1.427 g/cm³
• LogP: 4.04100

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-Acenocoumarol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: Acenocoumarol is a short-lived oral anti-coagulant, which, like warfarin, functions by inhibiting vitamin K epoxide reductase. It has higher intrinsic anticoagulant potency than warfarin and phenprocoumon, when evaluated in vitro. Acenocoumarol has a single chiral center that gives rise to two different enantiomeric forms. (S)-Acenocoumarol has a shorter plasma elimination half-life (1.8 hours) and faster plasma clearance (28.5 L/hour), compared to the (R)-enantiomer (6.6 hours, 1.9 L/hour). The S-enantiomer undergoes extensive first-pass metabolism during absorption from the gastrointestinal tract, whereas (R)-acenocoumarol is rapidly absorbed and provides essentially complete oral bioavailability. Perhaps related to these pharmacokinetic characteristics, (S)-acenocoumarol is less potent in vivo as an anti-coagulant than the (R)-enantiomer. As the clearance of acenocoumarol is ~20-fold faster than that for warfarin, the plasma concentrations of acenocoumarol are substantially lower than those for warfarin in patients receiving long-term treatment.
• Uses: S-Enantiomer of

Technology Process of (S)-(-)-Nicoumalone

There total 8 articles about (S)-(-)-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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