79950-42-8|2-Allyl-3-hydroxybenzaldehyde| Ambeed

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Quality Control of [ 79950-42-8 ] Purity: 97% (stabilized with TBC) SDS Specification

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Product Details of [ 79950-42-8 ]

CAS No. :	79950-42-8
Formula :	C₁₀H₁₀O₂
M.W :	162.19
SMILES Code :	O=CC1=CC=CC(O)=C1CC=C
MDL No. :	MFCD00100646
InChI Key :	QVHRAGBOMUXWRI-UHFFFAOYSA-N
Pubchem ID :	2775156

Safety of [ 79950-42-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 79950-42-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.1
Num. rotatable bonds	3
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	47.96
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	37.3 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.51
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.1
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.93
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.66
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.64
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.97

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.34
Solubility	0.74 mg/ml ; 0.00457 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.51
Solubility	0.497 mg/ml ; 0.00306 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.61
Solubility	0.397 mg/ml ; 0.00245 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.8 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	2.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.66

Application In Synthesis of [ 79950-42-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 79950-42-8 ]

[ 79950-42-8 ] Synthesis Path-Downstream 1~35

1
[ 40359-32-8 ]
[ 79950-42-8 ]

Yield	Reaction Conditions	Operation in experiment
33.3%	In decalin; at 180 - 190℃;	Compound (2) (600 g) was added to decahydronaphthalene (1800 ml) and the stirred reaction mixture was heated to 180 to 190 0C. Stirring was continued till completion of the reaction as monitored by HPLC. After completion, the reaction mixture was cooled and acetonitrile (4200 ml) was added to it. The acetonitrile layer was separated, concentrated. Toluene was added to the residue. The resulting mass was cooled, filtered. Optional treatment of the solid thus obtained using mixture of ethyl acetate and cyclohexane gave compound (3). Yield: 200 g (33.3%)
	In decalin; at 217℃; for 7h;Inert atmosphere;	Example 2. Preparation of 2-allyl-3-hvdroxy-benzaldehyde; [0022] In a 500 ml three-necked Morton flask equipped with mechanical stirrer, thermometer and reflux condenser was added 100 g of <strong>[40359-32-8]3-allyloxybenzaldehyde</strong> (0.62 moles, 1 eq.) and 150 g of cis/trans decalin (1 .5 vol). The mixture was purged with nitrogen and then heated to a reflux temperature of 217C. The reaction was maintained at this reflux temperature for seven hours then cooled and added of 231 mL of toluene. The reaction mixture was then allowed to cool to room temperature. After stirring for 18 hours and further cooling to 0-5 C for 1 -2 hours, reaction mixture was filtered and the cake washed with 200 mL of heptane. The wet cake was stirred in 200 mL of heptane for 1 -2 hours at room temperature. After filtration and drying of the cake at 40 C, 54.27 g of crude 2-allyl-3-hydroxy-benzaldehyde were obtained. This represents a recovery of 82% of the available 2-allyl product produced by the Claisen rearrangement.
	In decalin; at 217℃; for 7h;Inert atmosphere;	Example 2. Preparation of 2-allyl-3-hvdroxy-benzaldehyde 4; - 6 - 75907-27 (KB) [0017] In a 500 ml three-necked Morton flask equipped with mechanical stirrer, thermometer and reflux condenser was added 100 g of <strong>[40359-32-8]3-allyloxybenzaldehyde</strong> (0.62 moles, 1 eq.) and 150 g of cis/trans decalin (1 .5 vol). The mixture was purged with nitrogen and then heated to a reflux temperature of 217C. The reaction was maintained at this reflux temperature for seven hours then cooled and 231 mL of toluene was added.. The reaction mixture was then allowed to cool to room temperature. After stirring for 18 hours and further cooling to 0-5 C, reaction mixture was filtered and the cake washed with 200 mL of heptane. The wet cake was stirred in 200 mL of heptane for 1 -2 hours at room temperature. After filtration and drying of the cake at 40 C, 54.27 g of crude 2-allyl-3-hydroxy- benzaldehyde were obtained. This represents a recovery of 82% of the available 2-allyl product produced by the Claisen rearrangement.

In decalin; at 217℃; for 7h;Inert atmosphere;

In a 500 ml three-necked Morton flask equipped with mechanical stirrer, thermometer and reflux condenser was added 100 g of <strong>[40359-32-8]3-allyloxybenzaldehyde</strong> (0.62 moles,1 eq.) and 150 g of cis/trans decalin (1.5 vol). The mixture was purged with nitrogen and then heated to a reflux temperature of 217 C. The reaction was maintained at this reflux temperature for seven hours then cooled and added of 231 mL of toluene. The reaction mixture was then allowed to cool to room temperature. After stirring for 18 hours and further cooling to 0-5 C. for 1-2 hours, reaction mixture was filtered and the cake washed with 200 mL of heptane. The wet cake was stirred in 200 mL of heptane for 1-2 hours at room temperature. After filtration and drying of the cake at 40 C., 54.27 g of crude 2-allyl-3-hydroxy-benzaldehyde were obtained. This represents a recovery of 82% of the available 2-allyl product produced by the Claisen rearrangement.

References: [1]Organic Letters,2018,vol. 20,p. 7011 - 7014.
[2]Patent: WO2017/130109,2017,A1 .Location in patent: Page/Page column 25; 26.
[3]Journal of the American Chemical Society,1985,vol. 107,p. 1421 - 1423.
[4]Patent: WO2012/9816,2012,A1 .Location in patent: Page/Page column 10.
[5]Patent: WO2012/9818,2012,A1 .Location in patent: Page/Page column 6-7.
[6]Patent: US2013/331593,2013,A1 .Location in patent: Paragraph 0034; 0035.

2
[ 40359-32-8 ]
[ 79950-42-8 ]
[ 79950-43-9 ]

Yield	Reaction Conditions	Operation in experiment
47%	In tetralin; at 180 - 182℃;Microwave irradiation;	To a 3000 ml one neck, round bottom flask equipped with a condenser and thermometer was added allylether (7) (308 g) and tetrahydronaphthalene (300 mL). This reaction mixture was heated slowly up to 180-182° C. (ramped the temp. in 5-10 minutes, internal temperature) in a microwave (power: 1500 Watts) and was kept at this temperature while stirring for 7-8 h. At this stage the reaction mixture turned brown and the reaction mixture was cooled to room temperature followed by cooling at 0 to 5° C. for 30 minutes. The solid was filtered and dried to obtain off-white solid (3-hydroxy-2-allylbenzaldehyde, 8) 145.5 g (47percent).

References: [1]Patent: US2016/107973,2016,A1 .Location in patent: Paragraph 0034; 0035; 0036.
[2]Journal of the Chemical Society. Perkin transactions I,1981,p. 2677 - 2679.
[3]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2461 - 2470.
[4]Synlett,2012,vol. 23,p. 867 - 872.
[5]Tetrahedron Letters,2012,vol. 53,p. 2125 - 2128.
[6]European Journal of Organic Chemistry,2018,vol. 2018,p. 5605 - 5614.

3
[ 79950-42-8 ]
[ 74-88-4 ]
[ 94956-98-6 ]

References: [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 5605 - 5614.
[2]Journal of the American Chemical Society,1985,vol. 107,p. 1421 - 1423.
[3]Organic Letters,2017,vol. 19,p. 1870 - 1873.

4
[ 79950-42-8 ]
[ 106-95-6 ]
2-allyl-3-allyloxybenzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate; In N,N-dimethyl-formamide; at 25 - 35℃;	(0119) Potassium carbonate (100 g) was added to the solution of compound (3) (100 g) in DMF (200 ml). Allyl bromide (86.8 g) was gradually added to the reaction mixture and the resulting mixture was stirred at 25 to 35°C. (0120) After completion of the reaction, as monitored by TLC, the reaction mixture was quenched with water and extracted with methyl tertbutyl ether. The organic layer was concentrated to yield compound (4a). Yield: 110 g (88percent). (0121) JH NMR (300 MHz, DMSO-D6): delta 10.22 (s, 1H), 7.42 (m, 2H), 7.31 (dd, / = 5.85 and (0122) 1.14 Hz, 1H), 5.91 (m, 2H), 5.39 (m, 1H), 5.25 (m, 1H), 4.89 (m, 2H), 4.63 (m, 2H), 3.83 (0123) (m, 2H). (0124) M+H: 203.1

References: [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2461 - 2470.
[2]Patent: WO2017/130109,2017,A1 .Location in patent: Page/Page column 26.

5
[ 100-83-4 ]
[ 79950-42-8 ]

References: [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2461 - 2470.
[2]Patent: WO2012/9816,2012,A1 .
[3]Patent: WO2012/9818,2012,A1 .
[4]Patent: US2013/331593,2013,A1 .
[5]Organic Letters,2017,vol. 19,p. 1870 - 1873.
[6]Patent: WO2017/130109,2017,A1 .
[7]Organic Letters,2018,vol. 20,p. 7011 - 7014.

6
[ 79950-42-8 ]
[ 94957-00-3 ]