30982-08-2|Methyl 2-(acetoxymethyl)acrylate| Ambeed

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Quality Control of [ 30982-08-2 ] Purity: 95% SDS Specification

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Product Details of [ 30982-08-2 ]

CAS No. :	30982-08-2
Formula :	C₇H₁₀O₄
M.W :	158.15
SMILES Code :	C=C(COC(C)=O)C(OC)=O
MDL No. :	MFCD00129934
Boiling Point :	No data available
InChI Key :	IMOQCGSCOCUDGV-UHFFFAOYSA-N
Pubchem ID :	10313240

Safety of [ 30982-08-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 30982-08-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	0
Fraction Csp3	0.43
Num. rotatable bonds	5
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	37.86
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	52.6 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.15
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	0.4
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	0.28
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.	0.5
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	0.61
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.79

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-0.74
Solubility	28.6 mg/ml ; 0.181 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.07
Solubility	13.4 mg/ml ; 0.0849 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very 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	-0.87
Solubility	21.3 mg/ml ; 0.135 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	No
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	No
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.	-6.98 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)	1.88

Application In Synthesis of [ 30982-08-2 ]

* 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 [ 30982-08-2 ]

[ 30982-08-2 ] Synthesis Path-Downstream 1~35

1
[ 15484-46-5 ]
[ 108-24-7 ]
[ 30982-08-2 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,4-diaza-bicyclo[2.2.2]octane; 2-allyloxymethyl-acrylic acid methyl ester; at 50℃; for 2h;	Example 54; Acetic anhydride (87 g) as a derivatizing agent was added dropwise over a period of 1 hour to 371 g of the reaction mixture obtained in Example 53, and the mixture was stirred for 2 hours at 50C. The amount of methyl α-(hydroxyethyl) acrylate in 458 g of this reaction mixture was 2 g. The reaction mixture was then washed with water to remove the catalyst, following which purification was carried out by distillation using a distillation apparatus (theoretical number of plates, 13) and under reduced pressure (operating pressure, 2 kPa). The amount of reaction mixture prior to distillation was 450 g, and included 256 g of methyl α-(allyloxymethyl) acrylate, 1 g of methyl α-(hydroxymethyl) acrylate and 30 g of methyl α-(acetoxymethyl) acrylate. Following distillation, 192 g of product containing 99.3 wt% of methyl α-(allyloxymethyl) acrylate and 0.2 wt% of methyl α-(hydroxymethyl) acrylate was obtained.

References: [1]Organic Letters,2019,vol. 21,p. 9348 - 9352.
[2]Tetrahedron,1992,vol. 48,p. 8317 - 8328.
[3]Advanced Synthesis and Catalysis,2010,vol. 352,p. 1539 - 1553.
[4]Patent: EP2415751,2012,A1 .Location in patent: Page/Page column 63.
[5]Chemistry - A European Journal,2018,vol. 24,p. 4810 - 4814.

2
[ 120-72-9 ]
[ 30982-08-2 ]
[ 72629-44-8 ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 9865 - 9868.
[2]Tetrahedron Letters,2004,vol. 45,p. 8419 - 8422.

3
[ 52415-29-9 ]
[ 30982-08-2 ]
3-(2'-methoxycarbonyl-2'-propenyl)-6-bromoindole [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 9865 - 9868.
[2]Tetrahedron Letters,2004,vol. 45,p. 8419 - 8422.

4
[ 52488-36-5 ]
[ 30982-08-2 ]
3-(2'-methoxycarbonyl-2'-propenyl)-4-bromoindole [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 9865 - 9868.
[2]Tetrahedron Letters,2004,vol. 45,p. 8419 - 8422.

5
[ 1006-94-6 ]
[ 30982-08-2 ]
3-(2'-methoxycarbonyl-2'-propenyl)-5-methoxylindole [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 9865 - 9868.
[2]Tetrahedron Letters,2004,vol. 45,p. 8419 - 8422.

6
[ 30982-08-2 ]
[ 614-96-0 ]
3-(2'-methoxycarbonyl-2'-propenyl)-5-methylindole [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 9865 - 9868.
[2]Tetrahedron Letters,2004,vol. 45,p. 8419 - 8422.

7
[ 15484-46-5 ]
[ 75-36-5 ]
[ 30982-08-2 ]

Yield	Reaction Conditions	Operation in experiment
71%	With triethylamine; In dichloromethane; at 0 - 20℃;	Compound lb (232 mg, 2 mmol) was dissolved in 5 mL of DCM with TEA (220 mg, 2 mmol) and cooled to 0 C. To the solution, acetyl chloride (157 mg, 2 mmol) was added dropwise. The reaction mixture was stirred at room temperature after addition. After reaction, the reaction solution was collected by filtration and extracted with water for three times. The organic layers were collected and dried over anhydrous sodium sulfate. The solution was further filtered and concentrated to afford crude product which was subjected to flash chromatography to obtain pure compound 6. Yield: 224.4 mg, 71%. -NMR (400 MHz, CDCh): d 6.36 (s, 1H), 5.85 (s, 2H), 4.81 (s, 2H), 3.79 (s, 3H), 2.10 (s, 3H). 13C-NMR (100 MHz, CDCh): 5(ppm) 170.41, 165.68, 135.21, 127.60, 62.47, 52.06, 20.88.

References: [1]Organic Letters,2021,vol. 23,p. 3038 - 3042.
[2]Advanced Synthesis and Catalysis,2018,vol. 360,p. 2566 - 2570.
[3]Organic Letters,2021,vol. 23,p. 4986 - 4990.
[4]Patent: WO2020/6340,2020,A1 .Location in patent: Paragraph 00224.
[5]Advanced Synthesis and Catalysis,2008,vol. 350,p. 1610 - 1614.
[6]Organic Letters,2006,vol. 8,p. 3359 - 3362.

8
[ 30982-08-2 ]
[ 70219-84-0 ]
C₃₃H₃₈O₈ [ No CAS ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 12682 - 12683.

9
[ 30982-08-2 ]
[ 4374-93-0 ]
C₃₁H₄₂O₈ [ No CAS ]

References: [1]Journal of the American Chemical Society,2007,vol. 129,p. 12682 - 12683.

10
[ 30982-08-2 ]
Acetoxy-cyano-acetic acid ethyl ester [ No CAS ]
[ 1346232-14-1 ]

References: [1]Organic Letters,2011,vol. 13,p. 6164 - 6167.

11
[ 75-91-2 ]
[ 30982-08-2 ]
[ 100-52-7 ]
[ 1415690-16-2 ]

Yield	Reaction Conditions	Operation in experiment
79%	With iron(II) chloride; In decane; acetonitrile; at 85℃; for 1h;Inert atmosphere;	General procedure: To a mixture of alkene 1 (0.5 mmol), aldehyde 2 (2.5 mmol), and FeCl2 (1.6 mg, 0.0125 mmol), acetonitrile (3.0 mL) was added under nitrogen at room temperature. Then tert-butyl hydroperoxide 3 (TBHP, 2.0 mmol, 5-6 M in decane) was dropped into the mixture under nitrogen at room temperature. The resulting mixture was stirred under 85 oC for 1 h. The temperature of reaction was cooled to room temperature. The resulting reaction solution was directly filtered through a pad of silica by ethyl acetate. The solvent was evaporated in vacuo to give the crude products. NMR yields are determined by 1H NMR using dibromomethane as an internal standard. Solvent was evaporated and the residue was purified by flash column chromatography on silica gel with ethyl acetate/petroleum ether as eluent to afford the pure product 4.

References: [1]Tetrahedron,2012,vol. 68,p. 10333 - 10337.

12
[ 591-50-4 ]
[ 30982-08-2 ]
[ 124957-42-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With silver(I) acetate; palladium diacetate; acetic acid; at 50℃; for 5h;	General procedure: A mixture of 1a (79 mg, 0.5 mmol), iodobenzene (112 mg, 1.1 equiv), Pd(OAc)2 (6 mg, 5 mol%), AgOAc (92 mg,1.1 equiv), and AcOH (1.5 g, 50 equiv) was heated to 50 C for 5 h. After the aqueous extractive workup and column chromatographic purification process (hexanes/Et2O, 20:1), the product 2a was isolated as a colorless oil, 101 mg (86%). Other compounds were synthesized similarly, and the selected spectroscopic data of unknown compounds 2b, 2e-meta, 2e-ortho, 2h, 3a, 3emeta, 3f, and 3i are as follows.

References: [1]Tetrahedron Letters,2013,vol. 54,p. 419 - 423.

13
[ 30982-08-2 ]
[ 624-31-7 ]
Methyl (2E)-2-(acetoxymethyl)-3-(4-methylphenyl)prop-2-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With silver(I) acetate; palladium diacetate; acetic acid; at 50℃; for 12h;	General procedure: A mixture of 1a (79 mg, 0.5 mmol), iodobenzene (112 mg, 1.1 equiv), Pd(OAc)2 (6 mg, 5 mol%), AgOAc (92 mg,1.1 equiv), and AcOH (1.5 g, 50 equiv) was heated to 50 C for 5 h. After the aqueous extractive workup and column chromatographic purification process (hexanes/Et2O, 20:1), the product 2a was isolated as a colorless oil, 101 mg (86%). Other compounds were synthesized similarly, and the selected spectroscopic data of unknown compounds 2b, 2e-meta, 2e-ortho, 2h, 3a, 3emeta, 3f, and 3i are as follows.

References: [1]Tetrahedron Letters,2013,vol. 54,p. 419 - 423.

14
[ 615-37-2 ]
[ 30982-08-2 ]
[ 278171-22-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With silver(I) acetate; palladium diacetate; acetic acid; at 50℃; for 12h;	General procedure: A mixture of 1a (79 mg, 0.5 mmol), iodobenzene (112 mg, 1.1 equiv), Pd(OAc)2 (6 mg, 5 mol%), AgOAc (92 mg,1.1 equiv), and AcOH (1.5 g, 50 equiv) was heated to 50 C for 5 h. After the aqueous extractive workup and column chromatographic purification process (hexanes/Et2O, 20:1), the product 2a was isolated as a colorless oil, 101 mg (86%). Other compounds were synthesized similarly, and the selected spectroscopic data of unknown compounds 2b, 2e-meta, 2e-ortho, 2h, 3a, 3emeta, 3f, and 3i are as follows.

References: [1]Tetrahedron Letters,2013,vol. 54,p. 419 - 423.

15
[ 30982-08-2 ]
[ 51934-41-9 ]
[ 1417537-41-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With silver(I) acetate; palladium diacetate; acetic acid; at 50℃; for 12h;	General procedure: A mixture of 1a (79 mg, 0.5 mmol), iodobenzene (112 mg, 1.1 equiv), Pd(OAc)2 (6 mg, 5 mol%), AgOAc (92 mg,1.1 equiv), and AcOH (1.5 g, 50 equiv) was heated to 50 C for 5 h. After the aqueous extractive workup and column chromatographic purification process (hexanes/Et2O, 20:1), the product 2a was isolated as a colorless oil, 101 mg (86%). Other compounds were synthesized similarly, and the selected spectroscopic data of unknown compounds 2b, 2e-meta, 2e-ortho, 2h, 3a, 3emeta, 3f, and 3i are as follows.

References: [1]Tetrahedron Letters,2013,vol. 54,p. 419 - 423.

16
[ 30982-08-2 ]
[ 22445-41-6 ]
[ 1417537-35-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	With silver(I) acetate; palladium diacetate; acetic acid; at 50℃; for 12h;	General procedure: A mixture of 1a (79 mg, 0.5 mmol), iodobenzene (112 mg, 1.1 equiv), Pd(OAc)2 (6 mg, 5 mol%), AgOAc (92 mg,1.1 equiv), and AcOH (1.5 g, 50 equiv) was heated to 50 C for 5 h. After the aqueous extractive workup and column chromatographic purification process (hexanes/Et2O, 20:1), the product 2a was isolated as a colorless oil, 101 mg (86%). Other compounds were synthesized similarly, and the selected spectroscopic data of unknown compounds 2b, 2e-meta, 2e-ortho, 2h, 3a, 3emeta, 3f, and 3i are as follows.

References: [1]Tetrahedron Letters,2013,vol. 54,p. 419 - 423.

17
[ 4214-28-2 ]
[ 30982-08-2 ]
[ 1417537-37-1 ]

Yield	Reaction Conditions	Operation in experiment
84%	With silver(I) acetate; palladium diacetate; acetic acid; for 10h;Reflux;	General procedure: A mixture of 1a (79 mg, 0.5 mmol), iodobenzene (112 mg, 1.1 equiv), Pd(OAc)2 (6 mg, 5 mol%), AgOAc (92 mg,1.1 equiv), and AcOH (1.5 g, 50 equiv) was heated to 50 C for 5 h. After the aqueous extractive workup and column chromatographic purification process (hexanes/Et2O, 20:1), the product 2a was isolated as a colorless oil, 101 mg (86%). Other compounds were synthesized similarly, and the selected spectroscopic data of unknown compounds 2b, 2e-meta, 2e-ortho, 2h, 3a, 3emeta, 3f, and 3i are as follows.

References: [1]Tetrahedron Letters,2013,vol. 54,p. 419 - 423.

18
[ 30982-08-2 ]
[ 95-50-1 ]
C₁₃H₁₂Cl₂O₄ [ No CAS ]
C₁₃H₁₂Cl₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%; 40%	With palladium(II) trifluoroacetate; silver(I) acetate; Trimethylacetic acid; at 110℃; for 12h;	General procedure: A mixture of 1a (79 mg, 0.5 mmol), iodobenzene (112 mg, 1.1 equiv), Pd(OAc)2 (6 mg, 5 mol%), AgOAc (92 mg,1.1 equiv), and AcOH (1.5 g, 50 equiv) was heated to 50 C for 5 h. After the aqueous extractive workup and column chromatographic purification process (hexanes/Et2O, 20:1), the product 2a was isolated as a colorless oil, 101 mg (86%). Other compounds were synthesized similarly, and the selected spectroscopic data of unknown compounds 2b, 2e-meta, 2e-ortho, 2h, 3a, 3emeta, 3f, and 3i are as follows.

References: [1]Tetrahedron Letters,2013,vol. 54,p. 419 - 423.

19
[ 30982-08-2 ]
[ 541-73-1 ]
C₁₃H₁₂Cl₂O₄ [ No CAS ]
C₁₃H₁₂Cl₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%; 17%	With palladium(II) trifluoroacetate; silver(I) acetate; Trimethylacetic acid; at 110℃; for 12h;	General procedure: A mixture of 1a (79 mg, 0.5 mmol), iodobenzene (112 mg, 1.1 equiv), Pd(OAc)2 (6 mg, 5 mol%), AgOAc (92 mg,1.1 equiv), and AcOH (1.5 g, 50 equiv) was heated to 50 C for 5 h. After the aqueous extractive workup and column chromatographic purification process (hexanes/Et2O, 20:1), the product 2a was isolated as a colorless oil, 101 mg (86%). Other compounds were synthesized similarly, and the selected spectroscopic data of unknown compounds 2b, 2e-meta, 2e-ortho, 2h, 3a, 3emeta, 3f, and 3i are as follows.

References: [1]Tetrahedron Letters,2013,vol. 54,p. 419 - 423.

20
[ 30982-08-2 ]
[ 937-19-9 ]
[ 1497426-40-0 ]

References: [1]Journal of Organic Chemistry,2013,vol. 78,p. 11860 - 11873.

21
[ 30982-08-2 ]
[ 937-18-8 ]
[ 1497426-41-1 ]