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Chemical Structure| 38330-80-2 Chemical Structure| 38330-80-2

Structure of Methyl potassium malonate
CAS No.: 38330-80-2

Chemical Structure| 38330-80-2

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Product Details of [ 38330-80-2 ]

CAS No. :38330-80-2
Formula : C4H5KO4
M.W : 156.18
SMILES Code : O=C([O-])CC(OC)=O.[K+]
MDL No. :MFCD00014021
InChI Key :WWTULTKUWBKVGV-UHFFFAOYSA-M
Pubchem ID :2724687

Safety of [ 38330-80-2 ]

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

Computational Chemistry of [ 38330-80-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 0
Fraction Csp3 0.5
Num. rotatable bonds 3
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 22.46
TPSA ?

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

66.43 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

-9.2
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

-0.38
Log Po/w (WLOGP)?

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

-1.7
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.

-0.54
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

-0.48
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

-2.46

Water Solubility

Log S (ESOL):?

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

-0.37
Solubility 66.5 mg/ml ; 0.426 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.

-0.55
Solubility 43.8 mg/ml ; 0.281 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

0.32
Solubility 324.0 mg/ml ; 2.07 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

Yes
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.

-7.52 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

2.0
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

1.0 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)

1.57

Application In Synthesis of [ 38330-80-2 ]

* 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 [ 38330-80-2 ]

[ 38330-80-2 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 38330-80-2 ]
  • [ 22838-46-6 ]
  • [ 656808-19-4 ]
  • 2
  • [ 38330-80-2 ]
  • [ 2979-48-8 ]
  • [ 615-06-5 ]
  • 3
  • [ 3721-95-7 ]
  • [ 38330-80-2 ]
  • [ 137638-05-2 ]
YieldReaction ConditionsOperation in experiment
59 g 10300] Under argon 64.1 g cabonyldiimidazol (396 mmol) was added to 31.5 mL cyclobutanecarboxylic acid (330 mmol) in 300 mL THF within 10 minutes at tt. After 25 minutes 226 mL DCM, 77 g potassium 3-methoxy-3-oxopro- panoate (494 mmol) and 37.7 g magnesium chloride (396 mmol) were added subsequently, heated up to 56 C. within 2.5 hours, and stirred for another 3.5 hours. The resulting suspension was cooled to tt., 600 mL 2N aqueous hydrochloric acid was added to reach pH 2, another 800 mL water was added and the resulting biphasic solution was separated. The aqueous phase was extracted twice with 250 mL DCM, the combined organic phases were washed with half concentrated aqueous sodium chloride solution, dried over sodium sulfate, filtered and evaporated. The resulting methyl 3-cy- clobutyl-3-oxopropanoate (59 g, used for the next step without purification) was dissolved in 10 mL methanol, 378 mL 2M aqueous sodium hydroxide solution was added and the mixture was stirred for one hour. 100 mL TI3ME was added, the aqueous phase twice extracted with 50 mL TEME, combined aqueous phases filtered and cooled to 5 C. To that solution 65.1 mL concentrated aqueous hydrochloric acid was added to reach pH <1. 167 g solid sodium chloride was added and the mixture was four times extracted with 100 mLethyl acetate, organic phases washed with water, dried over sodium sulfate, and evaporated to yield 3-cyclobutyl-3-oxo- propanoic acid (43 g, used for the next step without purification) as a slightly yellow oil. This oil was dissolved in 508 mL THF and 53.1 g carbonyldiimidazol (328 mmol) were added carefully and stirred for 6 hours. To the resulting solution 50 mL water was added, the THF evaporated under reduced pressure, 200 mL DCM added and washed with 400 mL 2M aqueous hydrochloric acid, 200 mL 0.5M aqueous hydrochloric acid, 200 mL water. Aqueous phases were extracted with 100 mL DCM and combined organic phases were dried over sodium sulfate, filtered and evaporated. The suiting orange oil was purified by liquid chromatography over silica gel with DCM/methanol as eluent. Target fractions were combined and evaporated to yield 22 g 3-(cyclobutanecarbonyl)- 6-cyclobutyl-4-hydroxy-2H-pyran-2-one (89 mmol, 53%) as a slowly crystallizing oil.
  • 4
  • [ 39223-32-0 ]
  • [ 38330-80-2 ]
  • [ 1313546-66-5 ]
  • 5
  • [ 207981-46-2 ]
  • [ 38330-80-2 ]
  • [ 1449291-12-6 ]
  • 6
  • [ 1017553-74-0 ]
  • [ 38330-80-2 ]
  • 3-oxo-3-(2-pyridin-3-yl-cyclopropyl)propionic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% 52d) 3-Oxo-3-(2-pyridin-2-yl-cyclopropyl)-propionic acid methyl ester 1 ,10-carbonyldiimidazole (0.33 g, 2.02 mmol) was added portionwise over 5 min to a stirred solution of 2-pyridin-3-yl-cyclopropanecarboxylic acid (0.30 g, 1 .84 mmol) in anhydrous THF (5 mL) under argon. After 1 h, a mixture of MgCI2 (0.35 g, 3.68 mmol) and potassium hydrogen methyl malonate (0.86 g, 5.52 mmol) was added. After 7 h the mixture was concentrated under vacuum and diluted with ethyl acetate. The mixture was then washed with aqueous NaHS04 (1 M) and brine, and the organic phase dried over Na2S04, filtered, and concentrated to dryness to give the product, used without further purification (0.335 g, 83%). LC-MS m/z 220 (M + H) +, 0.99 (ret. time).
  • 7
  • [ 117997-81-6 ]
  • [ 38330-80-2 ]
  • C20H27NO7 [ No CAS ]
 

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