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Description
The progress of microwave-promoted reactions can be monitored by interfacing a Raman spectrometer with a scientific microwave
unit. It has been used to follow the base- reaction of salicylaldehyde with ethylacetoacetate to yield 3-acetylcoumarin in this paper.
Tags
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Raman spectroscopy
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Reaction monitoring
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User Data
- experimental physchem properties
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The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. See also: Melting Point
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- miscellaneous
Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts
2H-1-Benzopyran-2-one, 3-acetyl-
3-Acetyl-2H-chromen-2-one
Coumarin, 3-acetyl-
223-541-6
[EINECS/ELINCS]
3949-36-8
[RN]
3-acetylcoumarin
Validated by Experts, Validated by Users, Non-Validated, Removed by Users, Redirected by Users, Redirect Approved by Experts
214671_ALDRICH
AI3-61648
AIDS121027
AIDS-121027
EU-0067526
Maybridge1_000885
NCGC00016644-01
NCI60_002723
NSC 31678
NSC31678
More...
Prestwick0_000891
Prestwick1_000891
SPBio_002911
ZINC00057909
Less...
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LogP: |
ACD/LogP:
1.38
XLogP:
1.50
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# of Rule of 5 Violations: |
0
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ACD/LogD (pH 5.5): |
1.37
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ACD/LogD (pH 7.4): |
1.37
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ACD/BCF (pH 5.5): |
6.53
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ACD/BCF (pH 7.4): |
6.53
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ACD/KOC (pH 5.5): |
133.31
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ACD/KOC (pH 7.4): |
133.31
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#H bond acceptors: |
3
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#H bond donors: |
0
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#Freely Rotating Bonds: |
1
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Polar Surface Area: |
43.37
Å2
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Index of Refraction: |
1.583
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Molar Refractivity: |
48.96
cm3
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Molar Volume: |
146.3
cm3
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Polarizability: |
19.41
10-24cm3
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Surface Tension: |
49
dyne/cm
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Density: |
1.285
g/cm3
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Flash Point: |
179
°C
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Enthalpy of Vaporization: |
64.13
kJ/mol
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Boiling Point: |
391.6
°C at 760 mmHg
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Vapour Pressure: |
2.43E-06
mmHg at 25°C
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Log Octanol-Water Partition Coef (SRC):
Log Kow (KOWWIN v1.67 estimate) = 0.79
Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
Boiling Pt (deg C): 342.94 (Adapted Stein & Brown method)
Melting Pt (deg C): 98.66 (Mean or Weighted MP)
VP(mm Hg,25 deg C): 3.73E-005 (Modified Grain method)
Subcooled liquid VP: 0.000194 mm Hg (25 deg C, Mod-Grain method)
Water Solubility Estimate from Log Kow (WSKOW v1.41):
Water Solubility at 25 deg C (mg/L): 1.061e+004
log Kow used: 0.79 (estimated)
no-melting pt equation used
Water Sol Estimate from Fragments:
Wat Sol (v1.01 est) = 544.57 mg/L
ECOSAR Class Program (ECOSAR v0.99h):
Class(es) found:
Acrylates
Vinyl/Allyl Ketones
Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
Bond Method : 2.94E-009 atm-m3/mole
Group Method: Incomplete
Henrys LC [VP/WSol estimate using EPI values]: 8.705E-010 atm-m3/mole
Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
Log Kow used: 0.79 (KowWin est)
Log Kaw used: -6.920 (HenryWin est)
Log Koa (KOAWIN v1.10 estimate): 7.710
Log Koa (experimental database): None
Probability of Rapid Biodegradation (BIOWIN v4.10):
Biowin1 (Linear Model) : 0.8390
Biowin2 (Non-Linear Model) : 0.9813
Expert Survey Biodegradation Results:
Biowin3 (Ultimate Survey Model): 2.9010 (weeks )
Biowin4 (Primary Survey Model) : 3.7830 (days )
MITI Biodegradation Probability:
Biowin5 (MITI Linear Model) : 0.6532
Biowin6 (MITI Non-Linear Model): 0.7112
Anaerobic Biodegradation Probability:
Biowin7 (Anaerobic Linear Model): 0.0812
Ready Biodegradability Prediction: YES
Hydrocarbon Biodegradation (BioHCwin v1.01):
Structure incompatible with current estimation method!
Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
Vapor pressure (liquid/subcooled): 0.0259 Pa (0.000194 mm Hg)
Log Koa (Koawin est ): 7.710
Kp (particle/gas partition coef. (m3/ug)):
Mackay model : 0.000116
Octanol/air (Koa) model: 1.26E-005
Fraction sorbed to airborne particulates (phi):
Junge-Pankow model : 0.00417
Mackay model : 0.00919
Octanol/air (Koa) model: 0.00101
Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
Hydroxyl Radicals Reaction:
OVERALL OH Rate Constant = 29.3661 E-12 cm3/molecule-sec
Half-Life = 0.364 Days (12-hr day; 1.5E6 OH/cm3)
Half-Life = 4.371 Hrs
Ozone Reaction:
OVERALL Ozone Rate Constant = 5.670000 E-17 cm3/molecule-sec
Half-Life = 0.202 Days (at 7E11 mol/cm3)
Half-Life = 4.851 Hrs
Fraction sorbed to airborne particulates (phi): 0.00668 (Junge,Mackay)
Note: the sorbed fraction may be resistant to atmospheric oxidation
Soil Adsorption Coefficient (PCKOCWIN v1.66):
Koc : 41.65
Log Koc: 1.620
Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
Rate constants can NOT be estimated for this structure!
Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
Log BCF from regression-based method = 0.500 (BCF = 3.162)
log Kow used: 0.79 (estimated)
Volatilization from Water:
Henry LC: 2.94E-009 atm-m3/mole (estimated by Bond SAR Method)
Half-Life from Model River: 2.732E+005 hours (1.138E+004 days)
Half-Life from Model Lake : 2.98E+006 hours (1.242E+005 days)
Removal In Wastewater Treatment:
Total removal: 1.87 percent
Total biodegradation: 0.09 percent
Total sludge adsorption: 1.78 percent
Total to Air: 0.00 percent
(using 10000 hr Bio P,A,S)
Level III Fugacity Model:
Mass Amount Half-Life Emissions
(percent) (hr) (kg/hr)
Air 0.0577 3.12 1000
Water 37.3 360 1000
Soil 62.6 720 1000
Sediment 0.0722 3.24e+003 0
Persistence Time: 547 hr
Descriptors:
0, 0, 0, 0, 0, 0, 0, 4, 1, 0, 0, 0, 3, 5, 0, 0, 10, 1, 1, 1, 0, 0, 0, 0
| Category | Target | PDB Code | LASSO Score |
| Other Enzymes | COX-2, cyclooxygenase-2 | 1cx2 | 0.23 |
| Nuclear Hormone Receptors | PPARg, peroxisome proliferator activated receptor | 1fm9 | 0.08 |
| Other Enzymes | HIVRT, HIV reverse transcriptase | 1rt1 | 0.02 |
| Kinases | VEGFr2, vascular endothelial growth factor receptor | 1vr2 | 0.02 |
| Serine Proteases | FXa, factor Xa | 1f0r | 0.02 |
| Other Enzymes | AmpC, AmpC beta-lactamase | 1xgj | 0.02 |
| Other Enzymes | COX-1, cyclooxygenase-1 | 1p4g | 0.01 |
| Kinases | SRC, tyrosine kinase SRC | 2src | 0.01 |
| Other Enzymes | HMGR, hydroxymethylglutaryl-CoA reductase | 1hw8 | 0.01 |
| Metalloenzymes | PDE5, phosphodiesterase 5 | 1xp0 | 0.01 |
| Nuclear Hormone Receptors | MR, mineralocorticoid receptor | 2aa2 | 0.01 |
| Nuclear Hormone Receptors | PR, progesterone receptor | 1sr7 | 0.01 |
| Nuclear Hormone Receptors | ER, estrogen receptor; antagonist | 3ert | 0.01 |
| Serine Proteases | Thrombin | 1ba8 | 0.01 |
| Kinases | CDK2, cyclindependent kinase 2 | 1ckp | 0.00 |
| Other Enzymes | PNP, purine nucleoside phosphorylase | 1b8o | 0.00 |
| Folate Enzymes | DHFR, dihydrofolate reductase | 3dfr | 0.00 |
| Nuclear Hormone Receptors | ER, estrogen receptor; agonist | 1l2i | 0.00 |
| Metalloenzymes | ACE, angiotensin-converting enzyme | 1o86 | 0.00 |
| Other Enzymes | HIVPR, HIV protease | 1hpx | 0.00 |
| Other Enzymes | GPB, glycogen phosphorylase | 1a8i | 0.00 |
| Metalloenzymes | COMT, catechol O-methyltransferase | 1h1d | 0.00 |
| Serine Proteases | Trypsin | 1bju | 0.00 |
| Other Enzymes | ALR2, aldose reductase | 1ah3 | 0.00 |
| Other Enzymes | SAHH, S-adenosyl-homocysteine hydrolase | 1a7a | 0.00 |
| Kinases | FGFr1, fibroblast growth factor receptor kinase | 1agw | 0.00 |
| Other Enzymes | AChE, acetylcholinesterase | 1eve | 0.00 |
| Nuclear Hormone Receptors | RXRa, retinoic X receptor R | 1mvc | 0.00 |
| Other Enzymes | NA, neuraminidase | 1a4g | 0.00 |
| Folate Enzymes | GART, glycinamide ribonucleotide transformylase | 1c2t | 0.00 |
| Kinases | PDGFrb, platelet derived growth factor receptor kinase | N/A | 0.00 |
| Kinases | TK, thymidine kinase | 1kim | 0.00 |
| Metalloenzymes | ADA, adenosine deaminase | 1stw | 0.00 |
| Nuclear Hormone Receptors | AR, androgen receptor | 1xq2 | 0.00 |
| Kinases | HSP90, human heat shock protein 90 | 1uy6 | 0.00 |
| Other Enzymes | InhA, enoyl ACP reductase | 1p44 | 0.00 |
| Kinases | P38 MAP, P38 mitogen activated protein | 1kv2 | 0.00 |
| Other Enzymes | PARP, poly(ADP-ribose) polymerase | 1efy | 0.00 |
| Nuclear Hormone Receptors | GR, glucocorticoid receptor | 1m2z | 0.00 |
| Kinases | EGFr, epidermal growth factor receptor | 1m17 | 0.00 |
Comments: 1H NMR (400 MHz, CDCl3) d: 8.51 (s, 1H), 7.67 (m, 2H), 7.3 9(m, 2H), 2.73 (s, 3H).
[Nicholas E. Leadbeater & Jason R. Schmink "Use of Raman spectroscopy as a tool for in-situ monitoring of microwave-promoted reactions" Nature Protocols (2007) doi:10.1038/nprot.2007.453] Comments: 13C NMR (75.5 MHz, CDCl3) d: 195.5, 159.2, 155.3, 147.4, 134.4, 130.2, 125.0, 124.6, 118.3, 116.7
[Nicholas E. Leadbeater & Jason R. Schmink "Use of Raman spectroscopy as a tool for in-situ monitoring of microwave-promoted reactions" Nature Protocols (2007) doi:10.1038/nprot.2007.453]
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