Ethyl 3-Ethoxy-2-Propenoate

Cat.NO.:A159605 Purity:98%

Product Details of [ 1001-26-9 ]

CAS No. :	1001-26-9
Formula :	C₇H₁₂O₃
M.W :	144.17
SMILES Code :	O=C(OCC)/C=C/OCC
MDL No. :	MFCD00009863
InChI Key :	ITQFPVUDTFABDH-AATRIKPKSA-N
Pubchem ID :	5366269

Safety of [ 1001-26-9 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H315-H318-H335
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P310-P332+P313-P362-P403+P233-P405-P501
Class:	9
UN#:	3334
Packing Group:	Ⅲ

Computational Chemistry of [ 1001-26-9 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	0
Fraction Csp3	0.57
Num. rotatable bonds	5
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	37.66
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	35.53 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.44
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	1.06
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.1
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.	0.64
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	0.95
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.24

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.07
Solubility	12.2 mg/ml ; 0.0848 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.	-1.4
Solubility	5.78 mg/ml ; 0.0401 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	-0.96
Solubility	15.8 mg/ml ; 0.11 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	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.	-6.43 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.	0.56

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)	2.43

Application In Synthesis of [ 1001-26-9 ]

* 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.

Upstream synthesis route of [ 1001-26-9 ]
Downstream synthetic route of [ 1001-26-9 ]

[ 1001-26-9 ] Synthesis Path-Upstream 1~1

1
[ 1001-26-9 ]
[ 107047-10-9 ]
[ 481054-89-1 ]

References:

[1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 9, p. 1463 – 1467.

Yield	Reaction Conditions	Operation in experiment
100%	at 190 – 200℃; for 2h;	40 g of powder Zetaeta were washed with dilute hydrochloric acid once, H20 washed 3 times, washed once in methanol, acetone and once with 20 Mm Hg and 100 degrees Celsius for 10 minutes after drying, remove the nitrogen 25 g was added to 100 ml three Zetaeta Round-bottomed flask containing a catalytic amount of iodine was added 6 ml of anhydrous benzene was heated and stirred at reflux, was added over 45 minutes containing 8.35 grams, 0.05 mole of ethyl bromoacetate and 8.89 g XI, 0 06 mol triethylorthoformate XII. After the dropwise addition, the treated again take Zetaeta 6.25 g flour added to the system, after the reaction was refluxed for 6 hours, the reaction solution was transferred to a 100 ml ice-water and 50 g, excess acetic acid was added, the ether layer was separated, with washed with saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and concentrated under 1.5 mm Hg vacuum distillation, 79-81 ° C was collected as a colorless oil distillate 3, 3-ethoxy-propionate esters XIII2 8 g, yield 29.4percent; collected above to give the 2.8 g 3, 3-ethoxypropionate XIII at 190-200 degrees Celsius was heated under reflux for 2 hours with a delicate smell ., colorless liquid of ethyl acrylate, 3- XIV2 2 g, yield 100percent;. the 2.2 g, 152 mmol of ethyl acrylate, 3- XIV added to 7.5 ml of water and 7.5 ml two six ring oxygen mixed solvent, -10 degrees centigrade to cool large, slowly added 2.97 g after 16.72 mmol of NBS, the reaction 1 hour at room temperature, then 1.15 g, 15.2 mmol) was added thiourea after 1 hour at 80 ° C, ice-cooling, after addition of an excess of ammonia brown solid appeared, suction filtered to give a solid, after washing with water and drying give 1.4 g 2-aminothiazol-5-carboxylate XV of sitting Jie, The yield was 53.8percent
62.1 g	With potassium hydrogensulfate; at 100℃; for 5h;Inert atmosphere; Green chemistry;	In a three-necked flask, 91 g (0.5 mol) of trichloroacetyl chloride was added, and 54 g (0.75 mol) of vinyl ether was slowly added dropwise, and the mixture was dropped for about 1.5 hours. The temperature was controlled at 30 ° C for 5 hours, and then steamed under 40 ° C. The low-boiling by-product is obtained; after steaming, 66 g (0.65 mol) of triethylamine and 100 g of ethanol are added, and the reaction is kept at 35 ° C for 5 h, filtered, and the cake is recovered. The filtrate is evaporated under reduced pressure at 50 ° C or less; Add 6.8 g (0.05 mol) of potassium hydrogen sulfate, raise the temperature to 100 ° C, pass nitrogen gas, the flow rate of nitrogen is 300 mL / min, keep the reaction for 5 h, the reaction is finished, and distilled under reduced pressure to obtain 62.1 g of ethyl 3-ethoxyacrylate. The rate was 86.1percent, and the purity by gas phase normalization was 98.8percent