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Chemical Structure| 2386-37-0 Chemical Structure| 2386-37-0

Structure of 2386-37-0

Chemical Structure| 2386-37-0

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Product Details of [ 2386-37-0 ]

CAS No. :2386-37-0
Formula : C13H19NO4
M.W : 253.29
SMILES Code : O=C(OC)CCC1=C(C)NC(C(OCC)=O)=C1C
MDL No. :MFCD00030381
InChI Key :KKBICYRCYZAPRF-UHFFFAOYSA-N
Pubchem ID :291754

Safety of [ 2386-37-0 ]

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

Computational Chemistry of [ 2386-37-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 18
Num. arom. heavy atoms 5
Fraction Csp3 0.54
Num. rotatable bonds 7
Num. H-bond acceptors 4.0
Num. H-bond donors 1.0
Molar Refractivity 67.48
TPSA ?

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

68.39 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.85
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

2.11
Log Po/w (WLOGP)?

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

1.91
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.

1.21
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

3.31
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.28

Water Solubility

Log S (ESOL):?

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

-2.48
Solubility 0.832 mg/ml ; 0.00329 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.

-3.18
Solubility 0.169 mg/ml ; 0.000665 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

-3.75
Solubility 0.0446 mg/ml ; 0.000176 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.

-6.35 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

0.0
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<0.0
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)

2.69

Application In Synthesis of [ 2386-37-0 ]

* 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 [ 2386-37-0 ]

[ 2386-37-0 ] Synthesis Path-Downstream   1~32

  • 1
  • [ 37789-64-3 ]
  • [ 2386-37-0 ]
  • 2
  • [ 2386-37-0 ]
  • [ 100-51-6 ]
  • [ 99602-66-1 ]
YieldReaction ConditionsOperation in experiment
77% With sodium; at 190℃;Heating / reflux; c) Preparation of the Compound of Formula (4): A 2.5 l Keller round-bottomed flask equipped with a reflux condenser/distillation head, a thermometer, a dropping funnel and an argon conduit is loaded with a solution of compound (5) (95.00 g, 0.38 mol) in benzyl alcohol (685 ml) and heated to 120 C., which results in the azeotropic removal of minor amounts of water. The mixture is then heated to 190 C. The dropping funnel is loaded with a separately prepared solution of sodium (3 g) in benzyl alcohol (70 ml). This solution is added in 5 ml portions, which results in a vigorous reflux of the reaction mixture. The resulting methanol and ethanol are removed by semi-continuous distillation. The conversion is followed by HPLC. The reaction mixture is cooled to 150 C. and then transferred into a mixture of methanol (0.85 l), water (0.54 l) and acetic acid (10 ml). At 30 C., crystallization takes place rapidly. The mixture is stirred again at ambient temperature for 1 h. The product is isolated by filtration. The product is dried under reduced pressure, to give the compound (4) (113.30 g, 77%) in the form of an off-white solid.1H NMR (300 MHz, CDCl3): 2.16 (s, CH3), 2.27 (s, CH3), 2.47 (t, CH2), 2.71 (t, CH2), 4.70 (s, CH3), 5.08 (s, CH2), 5.28 (s, CH2), 7.40 (m, 10H), 8.60 (broad singlet, NH2).
  • 3
  • [ 2386-37-0 ]
  • [ 951999-56-7 ]
  • 4
  • [ 884336-84-9 ]
  • [ 2386-37-0 ]
  • 5
  • [ 6829-40-9 ]
  • [ 13984-53-7 ]
  • [ 2386-37-0 ]
  • 6
  • [ 2386-37-0 ]
  • [ 54474-50-9 ]
YieldReaction ConditionsOperation in experiment
49% With sodium hydroxide; water; for 1h;Heating / reflux; <strong>[2386-37-0]4-(2-Methoxycarbonyl-ethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester</strong> (Aldrich, 228 g, 0.9 mol) and 720 mL of 5 N sodium hydroxide were refluxed for one hour. Thin layer chromatography showed the hydrolysis to be complete. The stirred mixture was cooled to 50 C. and hydrochloric acid (10 N, 390 mL) was slowly added to give a pH of 2-3. The oil which separated solidified. The mixture was stirred and cooled to 4 C. The solids were collected by vacuum filtration, washed thoroughly with water and dried under vacuum at 40 C. to give 65.7 g (49% yield) of 3-(2,4-dimethyl-1H-pyrrol-3-yl)-propionic acid as a reddish solid.
49% [0184] <strong>[2386-37-0]4-(2-Methoxycarbonyl-ethyl)-3,5-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester</strong> (Aldrich, 228 g, 0.9 mol) and 720 mL of 5 N sodium hydroxide were refluxed for one hour. Thin layer chromatography showed the hydrolysis to be complete. The stirred mixture was cooled to 50 C. and hydrochloric acid (10 N, 390 mL) was slowly added to give a pH of 2-3. The oil which separated solidified. The mixture was stirred and cooled to 4 C. The solids were collected by vacuum filtration, washed thoroughly with water and dried under vacuum at 40 C. to give 65.7 g (49% yield) of 3-(2,4-dimethyl-1H-pyrrol-3-yl)-propionic acid as a reddish solid.
  • 7
  • [ 122676-34-0 ]
  • [ 2386-37-0 ]
  • 10
  • [ 13984-53-7 ]
  • [ 3849-21-6 ]
  • [ 2386-37-0 ]
  • 11
  • [ 2386-37-0 ]
  • 4,4'-Dipropionic acid-3,3',5,5'-tetramethyldipyrromethene hydrochloride [ No CAS ]
  • 13
  • [ 2386-37-0 ]
  • [ 54278-05-6 ]
  • 14
  • [ 2386-37-0 ]
  • 4,4'-Dimethylcarbonylethyl-3,3',5,5'-tetramethyldipyrromethene hydrochloride [ No CAS ]
  • 15
  • [ 2386-37-0 ]
  • [ 915-70-8 ]
YieldReaction ConditionsOperation in experiment
Example 1 Preparation of Compound la (1,7- bis (3-methoxy-3-propionyl) -3, 5-ethoxycarbonyl-2,6-dimethyl - dipyrrolium borane),Its associated reaction scheme is as follows: The 20. 3g (80mmol) dipyrrolium ester (Compound 1) was dissolved in 100ml of ethyl acetate. The 12.8g of liquid bromine (1 eq.) was added dropwise within 15min completion, after stirring for 1 hour to precipitate a pale yellow precipitate. The above reaction mixture was spin dried, and the solid was dissolved in 100ml of methanol, was added 2ml HC1 was refluxed for 1 hour, then cooled to 0 C, adjusted with 10% NH3 H20 pEta=7, a large number of solid precipitation. The solid was filtered off, washed with 70: 30 methanol: aqueous recrystallization. It was pure compound (2).
  • 17
  • [ 2386-37-0 ]
  • [ 114132-57-9 ]
  • 18
  • [ 2386-37-0 ]
  • [ 114132-55-7 ]
  • 19
  • [ 2386-37-0 ]
  • [ 114132-58-0 ]
  • 22
  • [ 2199-44-2 ]
  • [ 2386-37-0 ]
  • 23
  • [ 122676-31-7 ]
  • [ 2386-37-0 ]
  • 24
  • [ 122676-33-9 ]
  • [ 2386-37-0 ]
  • 25
  • [ 2386-37-0 ]
  • [ 20303-31-5 ]
  • 26
  • [ 2386-37-0 ]
  • [ 54605-86-6 ]
  • 27
  • [ 54278-10-3 ]
  • [ 2386-37-0 ]
  • 28
  • [ 2386-37-0 ]
  • 4-(2-benzylidenehydrazinocarbonyl-ethyl)-3,5-dimethyl-pyrrole-2-carboxylic acid ethyl ester [ No CAS ]
  • 29
  • [ 13984-53-7 ]
  • [ 16115-80-3 ]
  • [ 2386-37-0 ]
YieldReaction ConditionsOperation in experiment
28% With acetic acid; for 3.5h;Heating / reflux; b) Preparation of the Compound of Formula (5): A 4.5 l Keller round-bottomed flask equipped with a reflux condenser, a thermometer, a dropping funnel and an argon conduit is loaded with acetic acid (1.30 l) and refluxed. A solution of a mixture of compound (6) (248.71 g, 1.34 mol) and of dimethyl aminomalonate hydrochloride (367.50 g, 1.74 mol) in acetic acid (0.85 l) is added dropwise to the mixture at reflux, over 1 h. The mixture is again refluxed for 2.5 h. The conversion is followed by HPLC. The reaction mixture is cooled to ambient temperature and the acetic acid is eliminated by distillation under reduced pressure. The dark crude product is triturated with water (4.5 l), which is added slowly, portionwise. The mixture is mechanically stirred for a further 1 h and is then filtered, and the filtration cake is washed with water (1 l). The recrystallization of the dark gray crude product is carried out from ethanol/water (350/350 ml) by refluxing and then cooling to 10 C. The precipitate is isolated by filtration and washed with ethanol/water (4×100/100 ml). The product is dried under reduced pressure at ambient temperature, to give the compound (5) (95.00 g, 28%) in the form of a light purple-colored solid.1H NMR (300 MHz, CDCl3): 1.34 (t, CH3), 2.21 (s, CH3), 2.27 (s, CH3), 2.43 (t, CH2), 2.70 (t, CH2), 3.66 (s, CH3), 4.29 (q, CH2), 8.60 (broad singlet, NH2).
  • 30
  • [ 2386-37-0 ]
  • C50H64B2F4N4O16(2-)*2K(1+) [ No CAS ]
  • 31
  • [ 2386-37-0 ]
  • C25H31BF2N2O8(1-) [ No CAS ]
  • 32
  • [ 2386-37-0 ]
  • C50H64B2F4N4O16(2-)*2H4N2*2H(1+) [ No CAS ]
 

Historical Records

Technical Information

Categories

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[ 2386-37-0 ]

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