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Chemical Structure| 609-08-5 Chemical Structure| 609-08-5

Structure of 609-08-5

Chemical Structure| 609-08-5

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CAS No.: 609-08-5

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Product Citations

Product Citations

Jan Nowak ; Micha? Tryniszewski ; Micha? Barbasiewicz ;

Abstract: Heteroatom-based olefinating reagents (e.g., organic phosphonates, sulfonates, etc.) are used to transform carbonyl compounds into alkenes, and their mechanism of action involves aldol-type addition, cyclization, and fragmentation of four-membered ring intermediates. We have developed an analogous process using ethyl 1,1,1,3,3,3-hexafluoroisopropyl methylmalonate, which converts electrophilic aryl aldehydes into α-methylcinnamates in up to 70% yield. The reaction plausibly proceeds through the formation of β-lactone that spontaneously decarboxylates under the reaction conditions. The results shed light on the Knoevenagel–Doebner olefination, for which decarboxylative anti-fragmentation of aldol-type adducts is usually considered.

Keywords: olefination ; carbonyl compounds ; reaction mechanism ; lactones ; malonates ; Knoevenagel ; Doebner reaction

Purchased from AmBeed: ; ; ; ; ; ;

Alternative Products

Product Details of [ 609-08-5 ]

CAS No. :609-08-5
Formula : C8H14O4
M.W : 174.19
SMILES Code : O=C(OCC)C(C)C(OCC)=O
MDL No. :MFCD00009162
InChI Key :UPQZOUHVTJNGFK-UHFFFAOYSA-N
Pubchem ID :11857

Safety of [ 609-08-5 ]

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

Computational Chemistry of [ 609-08-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 0
Fraction Csp3 0.75
Num. rotatable bonds 6
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 43.14
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

52.6 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.36
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

1.44
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.75
Log Po/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.

0.93
Log Po/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

1.0
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.3

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-1.43
Solubility 6.45 mg/ml ; 0.0371 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.

-2.15
Solubility 1.23 mg/ml ; 0.00708 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

-1.27
Solubility 9.25 mg/ml ; 0.0531 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.

-6.34 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)

 1.73

Application In Synthesis of [ 609-08-5 ]

* 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 [ 609-08-5 ]

[ 609-08-5 ] Synthesis Path-Downstream   1~12

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  • [ 75-26-3 ]
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  • [ 3437-95-4 ]
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  • [ 704-38-1 ]
  • [ 14313-93-0 ]
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  • 6
  • [ 93-04-9 ]
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  • [ 27581-07-3 ]
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  • 7
  • [ 2106-50-5 ]
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  • 9
  • [ 609-08-5 ]
  • [ 103347-14-4 ]
  • C13H17ClO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Step 16B : Compound 16b; Diethyl methylmalonate (1.37 mL, 8.7 mmol) was added dropwise to suspension of NaH (60% in oil, 348 mg, 8.7 mol) in THF (20 mL). The generation off : was visible. The mixture was stirred for 0.5 h at room temperature and a solution of 16a (2.16 g, 9.2 mmol) in 10 mL THF and NaI (catalytic amount) was added. The reaction mixture was stirred overnight and then was worked up by adding H20 and extracting with Et2O twice. The combined organic layers were washed with brine, dried overNa2SO4, and concentrated to give a clear oil which was dissolved in 5 mL THF. MeOH (5 mL) and NaOH (2N, 20 mL) were added to the solution and the mixture was heated at 80 C for 4 h. After cooling, the mixture was extracted with Et2O and the aqueous solution was acidified using 6 N HC1. The solution was extracted with EtOAc three times. The organic layers were combined and washed with brine, dried over Na2SO4, filtered, and concentrated. The crude material was trituated with hexane to afford 16b as a white solid (885 mg, 3.86 mmol).
  • 10
  • [ 57297-29-7 ]
  • [ 609-08-5 ]
  • [ 870089-70-6 ]
YieldReaction ConditionsOperation in experiment
Example 16 Synthesis of 2-methyl-5-cyclopropyl-4,6-dihydroxy-pyrimidine A single-necked flask containing 80 ml of ethanol is cooled down to 0° C. using an ice bath, 4.5 g (66.4 mmoles) of sodium ethylate and 4 g (33.2 mmoles) of cyclopropyl-carbamidine hydrochloride are added. The reaction mixture is left to return to ambient temperature, then 5.7 ml (33.2 mmoles) of diethyl ester methylmalonate is added dropwise. Stirring is maintained at ambient temperature overnight. The ethanol is then condensed under reduced pressure (2 kPa). The crude product obtained is solubilized in a minimum amount of water (approximately 40 ml), then acidified at 0° C. with pure acetic acid until a pH comprised between 4 and 5 is achieved. The white precipitate formed is filtered, rinsed successively with water, ethyl ether and with pentane. Then the white powder obtained is dried over P2O5 under reduced pressure (0.2 kPa). 3 g of expected product is obtained. TLC: Rf=0.36 (silica gel, eluent: dichloromethane-methanol 90-10). MS: (MH+)=167, (MH-)=165 1H-NMR (DMSOd6): delta 0.95 (m, 4H, cyclopropyl); 1.67 (s, 3H, N=C-CH3); 1.83 (m, 1H, cyclopropyl).
  • 11
  • [ 3460-18-2 ]
  • [ 609-08-5 ]
  • [ 90725-50-1 ]
YieldReaction ConditionsOperation in experiment
4.9 g Sodium hydride (3.9 g) was suspended in dimethyl sulfoxide (24 mL), and diethyl methyl malonate (16 mL) was added at 0C, and then the reaction mixture was stirred at room temperature for 1.5 hours. The reaction mixture was heated to 100C, and a solution of 2,5-dibromonitrobenzene (15.3 g) in dimethyl sulfoxide (17 mL) was added at 100C, and then the reaction mixture was stirred at 100C for 5 hours. The reaction mixture was quenched with water, and extracted with ethyl acetate. The obtained organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethanol (75 mL), and tin (11.5 g) was added at room temperature. Concentrated hydrochloric acid (45 mL) was added at 0C, and then the reaction mixture was heated at reflux for 2 hours. After cooling to room temperature, the reaction mixture was quenched with water, and extracted with ethyl acetate. The obtained organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (4.9 g) as a brown solid. 1H-NMR (400 MHz, CDCl3) delta: 8.48 (1H, brs), 7.17 (1H, dd, J= 7.9, 1.3 Hz), 7.08 (1H, d, J = 7.9 Hz), 7.07 (1H, s), 3.41 (1H, q, J = 7.8 Hz), 1.48 (3H, d, J = 7.8 Hz). ESI-MS found: 226 [M+H]+
  • 12
  • [ 54288-70-9 ]
  • [ 609-08-5 ]
  • 2-methyl(4-piperidinyl)malonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
32.78% With potassium carbonate; In acetonitrile; at 40 - 60℃; Take 69.6g (0.4mol) of 2-methyl-malonic acid diethyl ester in a three-necked flask, add 55.2g (0.4mol) of anhydrous K2CO3 and stir with 500ml of acetonitrile.Another 4-bromopiperidine hydrobromic acid solution (containing 4-bromopiperidine 160.0g) was added to the reaction mixture, the oil bath heated to 40 ~ 60 ° C for 2-6h, insoluble matter was filtered off,The filtrate was drained and then dissolved in 1000 ml of ethyl acetate, washed with saturated aqueous NaCl (250 ml × 3 times) and the organic layer was dried over anhydrous magnesium sulfate overnight.The pump was depressurized to remove the solvent to obtain 105.1 g of yellowish reddish-brown transparent substance, which was purified by column chromatography to obtain 33.7 g of pure product in a yield of 32.78percent.
 

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