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Product Details of [ 73257-49-5 ]

CAS No. :73257-49-5
Formula : C17H18ClNO4
M.W : 335.78
SMILES Code : O=C(C1=C(C)NC(C)=C(C(OC)=O)C1C2=CC=C(Cl)C=C2)OC
MDL No. :MFCD00619418
InChI Key :XBDJVUHXRNRICA-UHFFFAOYSA-N
Pubchem ID :726133

Safety of [ 73257-49-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H320-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Computational Chemistry of [ 73257-49-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 23
Num. arom. heavy atoms 6
Fraction Csp3 0.29
Num. rotatable bonds 5
Num. H-bond acceptors 4.0
Num. H-bond donors 1.0
Molar Refractivity 90.71
TPSA ?

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

64.63 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.24
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

3.31
Log Po/w (WLOGP)?

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

2.54
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.

2.26
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

3.29
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.93

Water Solubility

Log S (ESOL):?

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

-3.87
Solubility 0.0453 mg/ml ; 0.000135 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.

-4.34
Solubility 0.0152 mg/ml ; 0.0000454 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately 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

-5.06
Solubility 0.00292 mg/ml ; 0.00000871 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately 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

Yes
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

Yes
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

Yes
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.0 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)

3.7

Application In Synthesis of [ 73257-49-5 ]

* 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.

  • Upstream synthesis route of [ 73257-49-5 ]

[ 73257-49-5 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 35929-79-4 ]
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  • [ 73257-49-5 ]
YieldReaction ConditionsOperation in experiment
91% With ammonium hydroxide In ethanol at 110℃; Flow reactor General procedure: Diethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate (4a). EtOH solution (3 mL) ofbenzaldehyde (0.67 M) mixed with ethyl acetoacetate (1.34 M) and the 25percent aqueous NH3 (3 mL) wererespectively transferred into gas-tight syringe 1 and syringe 2. The syringes were placed in a LongerLSP02-1B syringe pump which was set to deliver the reactants into the mixer at identical flow rate of 6.7μL/min. The reaction mixture was then allowed to flow through a stainless steel tube reactor which wasdipped in a 110 C oil bath. The output mixture was collected in a cooled sample vial. After reactioncompletion, rinsed the reactor with ethanol to collect all of the reactant solution and then concentratedunder vacuum. The residue was subjected to silica gel column chromatography with Pet-EA (5:1) aseluent to give 4a (612mg, 93percent yield).
References: [1] Heterocycles, 2016, vol. 93, # 2, p. 755 - 761.
  • 2
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  • [ 73257-49-5 ]
YieldReaction ConditionsOperation in experiment
96% With ammonium hydroxide; hydrogen bromide; dimethyl sulfoxide In water at 75℃; for 2.53333 h; General procedure: A mixture of HBr (48percent aq., 1 mmol) in DMSO (1 mL) was stirred for 2 min at 75 °C. Then, benzylic alcohol (1 mmol), alkyl acetoacetate (2 mmol), and ammonium hydroxide (1.5 mmol) were added to the reaction mixture and stirring was continued at 75 °C for 2.5 h. The completion of reaction was followed by TLC. After the reaction was complete, the reaction mixture was cooled to ambient temperature, quenched by addition of water (2 mL), and stirring was continued for 10 min at ambient temperature. The resulting precipitate was filtered, washed with water, dried, and recrystallized from ethanol to afford the pure product 4.
References: [1] Tetrahedron Letters, 2018, vol. 59, # 46, p. 4102 - 4106.
  • 3
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  • [ 73257-49-5 ]
YieldReaction ConditionsOperation in experiment
84% With ammonium acetate In neat (no solvent) at 55℃; for 3 h; Green chemistry General procedure: Polyhydroquinolines and DihydropyridinesA mixture of aldehyde (1 mmol), β-dicarbonyl compound (1or 2 mmol), NH4OAc (2.5 mmol), dimedone (1 mmol, whenused), and SBA-15/NHSO3H (5 molpercent) was stirred at 55 °C.After complete disappearance of starting material asindicated by TLC, the resulting mixture was diluted with hotEtOAc (10 mL) and filtered. The catalyst was completelyrecovered from the residue
References: [1] Synlett, 2014, vol. 25, # 19, p. 2753 - 2756.
  • 4
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YieldReaction ConditionsOperation in experiment
96% With iron supported on copper/Zeolite Socony Mobil-5 nanocatalyst In water at 20℃; Sonication General procedure: In a typical experiment, aromatic aldehyde (1 mmol), bketoester(2 mmol), ammonium acetate (1 mmol), and Fe-Cu/ZSM-5 (3 wtpercent) in 2 ml water were introduced in a 20-mL heavy-walled pear-shaped two-necked flask with nonstandard-tapered outer joint. The flask was attached to a12-mm tip diameter probe, and the reaction mixture was sonicated at ambient temperature at 20 percent power of the processor. After completion of the reaction (monitored byTLC, within 5–8 min), the solid product was filtered,washed with water and ethanol, dried, and recrystallized from ethanol. The supported reagent was washed thrice with water and ethanol and dried under vacuum before reuse.
References: [1] Journal of the Iranian Chemical Society, 2016, vol. 13, # 2, p. 267 - 277.
  • 5
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  • [ 105-45-3 ]
  • [ 73257-49-5 ]
YieldReaction ConditionsOperation in experiment
95% at 80℃; for 0.3 h; General procedure: A mixture of the alkyl or aryl aldehyde (1 mmol), -dicarbonyl(2 mmol) and ammonium acetate (1.5 mmol) in the presence ofFe3O4NPs (0.024 g, equal to 10 molpercent) was heated at 80C, withstirring. The progress of the reaction was monitored by TLC (elu-ent: EtOAc:n-hexane). After completion of the reaction, the mixturewas cooled to room temperature and then ethanol was added tothe resulting mixture and separated Fe3O4NPs by a normal mag-net. After evaporation of solvent, the solid product was filtered andrecrystallized from ethanol to give the pure products in 72–95percentyields based on the starting aldehyde.
95% With C23H3BF16N2O; ammonium acetate In toluene at 100℃; for 10 h; In a 100 mL single-necked flask, 0.01 molpercent of Lewis acid-base bifunctional catalyst I was added (where Rf = CF3R1,R2, R3, R4, R5, R6 = F), 0.1 mol of p-chlorobenzaldehyde (R7 = 4-Cl-Ph), 0.1 mol of methyl acetoacetate (R8 = Me;Me), 0.1 mol of ammonium acetate, 10 mL of toluene, and the reaction was stirred at 100 ° C for 10 hours. TLC followed the reaction to complete the reaction. anti-The yield of the product II (R7 = 4-Cl-Ph; R8 = Me; R9 = Me) was 95percent; the catalyst system was reused 10 timesAfter its catalytic performance did not decline
94% for 2.25 h; Heating; Green chemistry General procedure: A mixture of aldehyde 1 (1 mmol), 1,3-dicarbonyl compound 2 (2 mmol), and nitrogen source 3 (3 mmol) were mixed and heated in the presence of a low-melting sugar mixture.The progress of the reaction was monitored by thin-layer chromatography (TLC) using n-hexane–ethyl acetate (7:3) as the solvent system. The Rf values of the product spots ranged from 0.5 to 0.6. After completion of the reaction, water was added to the reaction mixture to obtain the solid product as a precipitate. In cases where the product was obtained as a melt, several washings with water followed by bicarbonate solution gave crystalline products. The solids were filtered and washed with cold water. In most of the cases, the product obtained was pure, and when impure, the product was recrystallized from hot ethanol. Further two products were obtained as oils (Table 5, entries 4w and 4x). These products were extracted with ethyl acetate and dried over anhydrous Na2SO4. Evaporation of the solvent gave the pure product as an oil.
91% at 100℃; for 0.25 h; Green chemistry General procedure: To a glassy reactor equipped with a magnetic stir bar, amixture of aromatic aldehyde (1.0 mmol), β-keto ester(2 mmol), ammonium acetate (1.5 mmol) and n-Fe3O4(at)ZrO2/HPW (0.003 g, 15 mol percent) was added. The reactorwas put in an oil bath with the temperature of 100 °C andthe reaction was carried out under solvent-free condition.The progress of the reaction was monitored using TLCplates. When the reaction was completed, the mixture wasallowed to cool to room temperature. Afterwards, the mixturewas triturated with 5mL ethyl acetate and the catalystwas separated by the help of an external magnet. Then thesolvent was evaporated and the crude product was recrystallizedfrom EtOH/H2O to offer the pure product.
90% With uranyl nitrate hexahydrate; ammonium acetate In ethanol at 20℃; for 0.416667 h; Sonication General procedure: To a solution of aldehyde (1.0 mmol), ethyl/methyl acetoacetate/acetylacetone (2.0 mmol) and ammonium acetate (1.0 mmol) in ethanol (3 mL), uranyl nitrate (10 molpercent) was added and the resultant reaction mixture was sonicated at room temperature for the required time (Table 1). The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was poured into crushed ice. The obtained solid was filtered, washed thoroughly with water, dried, and purified by recrystallisation in ethanol.

References: [1] RSC Advances, 2014, vol. 4, # 100, p. 56658 - 56664.
[2] Tetrahedron Letters, 2010, vol. 51, # 8, p. 1187 - 1189.
[3] Advanced Synthesis and Catalysis, 2012, vol. 354, # 10, p. 2001 - 2008.
[4] Journal of Molecular Catalysis A: Chemical, 2014, vol. 382, p. 99 - 105.
[5] Patent: CN107141249, 2017, A, . Location in patent: Paragraph 0114; 0115.
[6] Synthetic Communications, 2016, vol. 46, # 24, p. 1989 - 1998.
[7] RSC Advances, 2014, vol. 4, # 21, p. 10514 - 10518.
[8] Journal of the Indian Chemical Society, 2009, vol. 86, # 9, p. 996 - 1000.
[9] New Journal of Chemistry, 2018, vol. 42, # 15, p. 12539 - 12548.
[10] Journal of Heterocyclic Chemistry, 2008, vol. 45, # 3, p. 737 - 739.
[11] Catalysis Letters, 2017, vol. 147, # 6, p. 1551 - 1566.
[12] Chemical Communications, 2011, vol. 47, # 32, p. 9230 - 9232.
[13] Research on Chemical Intermediates, 2015, vol. 41, # 9, p. 6877 - 6883.
[14] Journal of the Chinese Chemical Society, 2016, vol. 63, # 4, p. 336 - 344.
[15] Synthesis, 2007, # 18, p. 2835 - 2838.
[16] Organic Preparations and Procedures International, 2012, vol. 44, # 2, p. 153 - 158.
[17] Synthetic Communications, 2004, vol. 34, # 23, p. 4349 - 4357.
[18] Synthetic Communications, 2009, vol. 39, # 11, p. 1957 - 1965.
  • 6
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References: [1] Journal of Materials Chemistry A, 2013, vol. 1, # 37, p. 11210 - 11220.
  • 7
  • [ 104-88-1 ]
  • [ 14205-39-1 ]
  • [ 105-45-3 ]
  • [ 73257-49-5 ]
References: [1] Tetrahedron Letters, 1995, vol. 36, # 44, p. 8083 - 8086.
  • 8
  • [ 67-56-1 ]
  • [ 104-88-1 ]
  • [ 72324-39-1 ]
  • [ 73257-49-5 ]
References: [1] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 5, p. 745 - 747.
  • 9
  • [ 104-88-1 ]
  • [ 105-45-3 ]
  • [ 14205-39-1 ]
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References: [1] Organic Process Research and Development, 2001, vol. 5, # 4, p. 452 - 455.
  • 10
  • [ 104-88-1 ]
  • [ 105-45-3 ]
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References: [1] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995, vol. 34, # 7, p. 652 - 653.
  • 11
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References: [1] Synthesis, 2010, # 23, p. 4057 - 4060.
 

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