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Structure of 70627-52-0

Chemical Structure| 70627-52-0

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Product Details of [ 70627-52-0 ]

CAS No. :70627-52-0
Formula : C20H16FNO
M.W : 305.35
SMILES Code : FC1=CC=C(C=C1)/N=C/C2=CC=C(OCC3=CC=CC=C3)C=C2
MDL No. :MFCD00017951
InChI Key :IWNBEFDVKWCBFY-UHFFFAOYSA-N
Pubchem ID :791783

Safety of [ 70627-52-0 ]

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

Computational Chemistry of [ 70627-52-0 ] Show Less

Physicochemical Properties

Num. heavy atoms 23
Num. arom. heavy atoms 18
Fraction Csp3 0.05
Num. rotatable bonds 5
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 91.07
TPSA ?

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

21.59 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.6
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

4.79
Log Po/w (WLOGP)?

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

5.42
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.

4.47
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

5.77
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.81

Water Solubility

Log S (ESOL):?

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

-5.0
Solubility 0.00305 mg/ml ; 0.00001 mol/l
Class?

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

Moderately soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-4.98
Solubility 0.00323 mg/ml ; 0.0000106 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

-7.93
Solubility 0.00000355 mg/ml ; 0.0000000116 mol/l
Class?

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

Poorly 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

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

Yes
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.

-4.76 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

1.0
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)

2.55

Application In Synthesis of [ 70627-52-0 ]

* 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.

  • Upstream synthesis route of [ 70627-52-0 ]

[ 70627-52-0 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 4397-53-9 ]
  • [ 371-40-4 ]
  • [ 70627-52-0 ]
YieldReaction ConditionsOperation in experiment
95% at 40℃; P-Fluoroaniline (100 g, 1.1 eq) and isopropanol (1730 ml, 10 V) were added and heated to 40 ° C. with mechanical stirring to precipitate a large amount of a pale yellow crystalline solid gradually, Stir over time and monitor until reaction is complete. The heating was stopped, the temperature was naturally lowered to room temperature while stirring, extraction and filtration were carried out, the filter cake was washed off with cold isopropanol, and after drying, a pale yellow crystalline substance SM 2 was obtained, the mass was 238 g , The yield is 95percent, and the purity is 99percent.
93.6% Reflux; Large scale The p-fluoroaniline (1.11kg, 10mol) and 4-benzyloxybenzaldehyde (2.12kg, 10mol) were added to 10L of toluene and refluxed. After the reaction was completed, the solvent was evaporated and the solvent was normal. n-hexane and ethyl acetate 10:1 Crystallization gave Compound 4 (2.85 kg) in 93.6percent yield.
References: [1] Patent: JP2016/147843, 2016, A, . Location in patent: Paragraph 0016.
[2] Patent: CN107793339, 2018, A, . Location in patent: Paragraph 0021; 0023; 0031; 0038.
[3] Pharmacy and Pharmacology Communications, 2000, vol. 6, # 1, p. 25 - 29.
[4] Journal of Organic Chemistry, 2018, .
  • 2
  • [ 100-39-0 ]
  • [ 123-08-0 ]
  • [ 371-40-4 ]
  • [ 70627-52-0 ]
YieldReaction ConditionsOperation in experiment
92%
Stage #1: at 20℃; for 12 h;
Stage #2: for 4 h; Reflux
100 ml of DMF, p-hydroxybenzaldehyde (12.2 g, 0.1 mol), potassium carbonate (16.6 g, 0.12 mol) were successively added to a 250 ml three-necked flask, Benzyl bromide (20.4 g, 0.12 mol) was added dropwise, Room temperature reaction for 12 hours, The reaction solution was poured into ice water, Solid precipitation,filter, Washed cake, The filter cake is dry. To give benzyl-protected p-hydroxybenzaldehyde (26.2 g)Yield 91percent. And then take another 250ml single neck round bottom flask, Followed by adding 100 ml of acetone, benzyl-protected p-hydroxybenzaldehyde (14.4 g, 0.05 mol), p-fluoroaniline (5.55 g, 0.05 mol) After the reaction was refluxed for 4 h, the reaction solution was cooled to 5 ° C to precipitate a solid, filter, The solid was washed with cold acetone, The solid was dried to give N-(4-fluorophenyl)-4-benzyloxybenzylideneamine (Compound IV) 14g, Yield 92percent.
References: [1] Patent: CN106397292, 2017, A, . Location in patent: Paragraph 0092; 0093.
[2] Patent: WO2008/96372, 2008, A2, . Location in patent: Page/Page column 17.
  • 3
  • [ 3382-63-6 ]
  • [ 100-44-7 ]
  • [ 70627-52-0 ]
YieldReaction ConditionsOperation in experiment
20.3 g With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2 h; The formula EZ-2 is a structural formula of 4-[[(4-fluorophenyl)imino]methyl]-phenol.4-[[(4-Fluorophenyl)imino]methyl]-phenol (21.5 g, 0.1 mol) was dissolved in 20 ml of DMF.Potassium carbonate (27.6 g, 0.2 mol) was added in sequenceChlorobenzyl (12.6 g, 0.1 mol),After the addition, the mixture was stirred at room temperature for 2 h.TLC judged the end of the reaction, poured the reaction solution into ice water, and filtered by suction.The filter cake was dried in vacuo to give a white solid (20.3 g).
References: [1] Patent: CN109369491, 2019, A, . Location in patent: Paragraph 0036-0039; 0060-0062.
  • 4
  • [ 123-08-0 ]
  • [ 70627-52-0 ]
References: [1] Patent: JP2016/147843, 2016, A, .
  • 5
  • [ 100-44-7 ]
  • [ 70627-52-0 ]
References: [1] Patent: JP2016/147843, 2016, A, .
  • 6
  • [ 99395-88-7 ]
  • [ 70627-52-0 ]
References: [1] Patent: CN105439929, 2016, A, . Location in patent: Paragraph 0029.
 

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