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Chemical Structure| 712353-75-8 Chemical Structure| 712353-75-8

Structure of 712353-75-8

Chemical Structure| 712353-75-8

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Product Details of [ 712353-75-8 ]

CAS No. :712353-75-8
Formula : C13H15NO3
M.W : 233.26
SMILES Code : O=C(C1)N(CC2=CC=C(OC)C=C2)CCC1=O
MDL No. :MFCD17011792
InChI Key :RWBJCFIEUAGKDV-UHFFFAOYSA-N
Pubchem ID :46835622

Safety of [ 712353-75-8 ]

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

Computational Chemistry of [ 712353-75-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 17
Num. arom. heavy atoms 6
Fraction Csp3 0.38
Num. rotatable bonds 3
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 67.03
TPSA ?

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

46.61 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.07
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

0.84
Log Po/w (WLOGP)?

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

0.85
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.

0.78
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

2.24
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.36

Water Solubility

Log S (ESOL):?

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

-1.88
Solubility 3.08 mg/ml ; 0.0132 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 9.25 mg/ml ; 0.0397 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

-3.44
Solubility 0.0849 mg/ml ; 0.000364 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.

-7.13 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<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)

1.37

Application In Synthesis of [ 712353-75-8 ]

* 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 [ 712353-75-8 ]

[ 712353-75-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 712353-75-8 ]
  • [ 100063-22-7 ]
  • [ 712353-76-9 ]
YieldReaction ConditionsOperation in experiment
49% A suspension of methyl 3-amino, 5-phenylthiophene 2- carboxylate (459mg, 1.96mmol) and 1- (4-Methoxy-benzyl)- piperidine-2,4-dione (457mg, 1. 96MMOL) at 21, under N2, was treated with dibutyltin dichloride (29mg, 0.098mmol, 5mol%) followed after 5min with phenylsilane (266DOL, 233mg, 2.15mmol, L. leq). The HETEROGENOUS mixture was stirred for 18h at 21 when a clear solution resulted. The reaction was left a further 5H, then evaporated to a thick oil (1.27g). The crude material was purified over silica using (Hexanes : CH2CL2 : EtOAc = 1: 1 : 1) as eluent to deliver 3- [1- (4-METHOXY-BENZYL)-2-OXO-PIPERIDIN-4-YLAMINO]-5- (1- methyl-hexa-1, 3,5-trienyl)-thiophene-2-carboxylic acid methyl ester as a yellow foam (432mg, 49%) (300MHz, CDCl3) 1.8-1.9(m, 1H), 2.25-2. 44 (m, 1H), 2.95 (dd, J = 1. 5Hz, J = 3. 9OHZ, 1H), 3.98 (dd, J = 1. 5Hz, J = 3. 9OHZ, 1H), 3.22-3. 40 (m, 4H), 3.80 (s, 3H), 3.33 (s, 3H), 3.85- 3.93 (m, 1H), 4.08 (m, 2H), 6.81 (s, 1H), 6.85-6. 9 (m, 2H), 7.20-7. 24 (m, 2H), 7. 36-7. 42 (m, 3H), 7.59-7. 61 (m, 2H).
  • 2
  • [ 712353-74-7 ]
  • [ 712353-75-8 ]
YieldReaction ConditionsOperation in experiment
69% A mixture of an hydrous K2CO3 (3.2g, 23.2mmol, 5eq) and 18-crown-6 (azetroped several times with toluene) (122mg, 0. 464MMOL, 10MOL%) in dry toluene (4ML), under nitrogen, was heated to reflux and then treated, dropwise, over 40min, with a solution of N- (4-METHOXY- BENZYL)-N- (2-METHOXYCARBONYL-ETHYL)-MALONAMIC acid methyl ester. After 7h at reflux the reaction was diluted with water (4ML) and toluene (4ml), then cooled to 0 and carefully acudified to pH 1.7 with 0. 1N HC1. The mixture was then extracted several times with CH2C12 (3X80ML) and the combined organics dried and evaporated to a brown oil (1.33g). The brown oil was treated with 10% aqueous oxalic acid and heated to reflux for 6.5h. The mixture was then extracted repratedly with CH 2CL2 and the combined organics dried and evaporated to a dirty yellow oil (1.03g). The crude material was purified on silica gel using (CH2CL2 : MEOH 30: 1) as eluent to give 1- (4-METHOXY-BENZYL)- piperidine-2,4-dione as a pale brown solid (750mg, 69%) ; (300MHZ, CDC1 3) 2. 52 (T, J = 5.7HZ, 2H), 3.41 (s, 2H), 3.47 (t, J = 5.7Hz, 2H), 3.80 (s, 3H), 4.62 (s, 2H), 6.16-6. 88 (m, 2H), 7.20 (m, 2H).
  • 3
  • [ 712353-75-8 ]
  • piperidine-2-carbaldehyde hydrochloride [ No CAS ]
  • 2-[(4-methoxyphenyl)methyl]-3,4,5,6,7,8,9-hexahydropyrido[3,4-b]indolizin-1-one [ No CAS ]
 

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