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Chemical Structure| 1439-36-7 Chemical Structure| 1439-36-7

Structure of 1439-36-7

Chemical Structure| 1439-36-7

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Product Details of [ 1439-36-7 ]

CAS No. :1439-36-7
Formula : C21H19OP
M.W : 318.35
SMILES Code : CC(C=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)=O
MDL No. :MFCD00008774
InChI Key :KAANTNXREIRLCT-UHFFFAOYSA-N
Pubchem ID :15038

Safety of [ 1439-36-7 ]

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

Computational Chemistry of [ 1439-36-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 23
Num. arom. heavy atoms 18
Fraction Csp3 0.05
Num. rotatable bonds 4
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 102.08
TPSA ?

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

26.88 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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

3.57
Log Po/w (WLOGP)?

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

3.37
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.

4.63
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

5.66
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.45

Water Solubility

Log S (ESOL):?

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

-4.38
Solubility 0.0133 mg/ml ; 0.0000419 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.

-3.82
Solubility 0.0482 mg/ml ; 0.000151 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

-7.91
Solubility 0.00000396 mg/ml ; 0.0000000124 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

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.

-5.71 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)

4.22

Application In Synthesis of [ 1439-36-7 ]

* 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 [ 1439-36-7 ]

[ 1439-36-7 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 121-33-5 ]
  • [ 1439-36-7 ]
  • [ 1080-12-2 ]
YieldReaction ConditionsOperation in experiment
98% In water; at 90℃; for 0.5h;Green chemistry; General procedure: A suspension of an appropriate aromatic aldehyde (1 eq.), and ylide I or II (1.3-1.5 eq.) inwater (4-10 mL) was stirred at 90 C for 0.5-24 h. Next, the heterogeneous reaction mixturewas cooled to room temperature, and the aqueous phase was extracted with DCM (3 10 mL).The solvent was evaporated under diminished pressure. Column chromatography (hexane-ethylacetate, or chloroform-methanol) of the residue gave the E-alkene as the major product.
  • 2
  • [ 2136-75-6 ]
  • [ 1439-36-7 ]
  • [ 13937-08-1 ]
  • [ 66085-96-9 ]
  • 3
  • [ 16583-06-5 ]
  • [ 1439-36-7 ]
  • (E)-4-(2,3,4,5-tetrafluorophenyl)but-3-en-2-one [ No CAS ]
  • (Z)-4-(2,3,4,5-tetrafluorophenyl)but-3-en-2-one [ No CAS ]
  • 4
  • [ 28785-06-0 ]
  • [ 1439-36-7 ]
  • [ 1356967-24-2 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; at 20℃; for 12h; General procedure: All aldehydes were previously prepared or purchased. Aldehyde 1 (5.0 mmol) was dissolved in THF (20 mL), and 1-(triphenylphosphoranylidene)-2-propanone (1.60 g, 5.0 mmol) was added. The mixture was allowed to stir at room temperature for 12 h. Solvent was removed under vacuum, and the residue was purified by flash column chromatography to provide 2, which was used directly in the next step, in almost quantitative yield.Compound 2 (2.0 mmol) and diethyl malonate (2.0 mmol) were dissolved in EtOH (5 mL), and a NaOEt solution (21 wt percent in ethanol; 1.50 mL, 4.0 mmol) was added. After being stirred for 12 h, 3 N aq NaOH (20 mL) was added, and stirring was continued for another 12 h. Aqueous 3 N HCl was added until the solution turned cloudy. Ether was used to extract the cloudy mixture until the aqueous layer was clear. The combined organic portions were combined and allowed to stir for 4 h until decarboxylation was complete. Heating might be required in some cases when decarboxylation was not complete at room temperature. The solvent was evaporated, and the crude product was then purified by recrystallization or flash chromatography. The CHD product was typically a white solid, obtained in about an 80percent yield, and had an Rf = 0.6 (dichloromethane/methanol = 8:1).
  • 5
  • [ 5780-66-5 ]
  • [ 1439-36-7 ]
  • [ 1414846-58-4 ]
  • 6
  • [ 100-10-7 ]
  • [ 1439-36-7 ]
  • [ 5432-53-1 ]
  • 7
  • [ 4565-31-5 ]
  • [ 1439-36-7 ]
  • (E)-N-hydroxy-5-(3-oxobut-1-en-1-yl)thiophene-2-carboxamide [ No CAS ]
  • 8
  • [ 109466-84-4 ]
  • [ 1439-36-7 ]
  • (E)-4-(2-amino-4-nitrophenyl)but-3-en-2-one [ No CAS ]
  • 9
  • [ 146137-78-2 ]
  • [ 1439-36-7 ]
  • 4-[2-fluoro-(5-trifluoromethyl)phenyl]-2-butanone [ No CAS ]
  • 10
  • [ 4313-03-5 ]
  • [ 1439-36-7 ]
  • 3E,5E-8-phenylocta-3,5-dien-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% In chloroform;Reflux; A solution of 1-hexyne (0.8 g, 10.0 mmol) in dry THF (50 mL) was magnetically stirred and cooled to -78 °C under N2 atmosphere This was followed by the slow addition of n-BuLi (1.6 M in THF, 10.0 mmol).The resulting reaction mixture was stirred at -78 C for 30 min, and then methyl chloroformate (1.3 g,14.0 mmol) was added. The reaction was stirred at -78 C for 30 min more and a saturated aqueoussolution of NH4Cl (20 mL) was added. The aqueous layer was separated and extracted with ethyl acetate(3 x 20 mL), and the combined organic layers were dried over Na2SO4, filtered and concentrated underreduced pressure. The crude product was purified by silica gel chromatography (ethyl acetate/hexane =5/95) to afford 7 (1.1 g, 8.0 mmol, 80percent yield). This was then treated with Ph3P and PhOH (0.4 eq. each)in PhMe at 50 C under an argon atmosphere to perform the alkyne to diene isomerization. After 1H NMRanalysis indicated that the reaction was completed, the mixture was cooled to room temperature andconcentrated under reduced pressure. The resulting mixture was purified by silica gel chromatography(CH2Cl2/hexane = 10/90, then ethyl acetate/hexane = 10/90) to afford the corresponding dienoate (1.0 g,89percent yield). This was dissolved in dry CH2Cl2 (50 mL) and DIBAL-H (2.5 eq.) was added at 0 C under aN2 atmosphere. After 45 min the reaction was quenched using MeOH/CH2Cl2 solution (1 mL/5 mL), andthe resulting mixture was washed with 1N aqueous HCl (3 x 20 mL), water (3 x 10 mL), brine (3 x 10mL), dried over Na2SO4, filtered and concentrated under reduced pressure to afford the correspondingdienol. This was used without further purification and dissolved in CH2Cl2 (50 mL), and reacted withMnO2 (8.0 eq.) at room temperature under an argon atmosphere. After TLC analysis indicated that thereaction was completed, the reaction mixture was filtered, concentrated under reduced pressure to affordthe crude 8 (0.6 g, 75percent yield). This was dissolved CHCl3 (50 mL) and 9 (1.5 eq.) was added, and thereaction mixture was heated to reflux. After TLC analysis indicated that the reaction was completed, thereaction mixture was concentrated under reduced pressure and purified by silica gel chromatography(ethyl acetate/hexane = 10/90) to afford 2o (0.5 g, 32percent overall yield).
  • 11
  • [ 555-16-8 ]
  • [ 1439-36-7 ]
  • [ 30780-19-9 ]
YieldReaction ConditionsOperation in experiment
86.9% (1) Dissolve 9.06g p-nitrobenzaldehyde and 19.75 acetyltriphenylphosphine in 100mL dichloromethane, react at 60C for 8 hours, then cool to room temperature, add 6mL trichlorosilane to the solution, add 6mL after reacting for 3 hours Trichlorosilane. After the completion, add 200mL saturated NaHCO3 and stir for 2 hours. The post-treatment is the same as step 1 in Example 1, to obtain 10.0g of the compound of formula 1 with a yield of 86.9%.
  • 12
  • [ 50461-74-0 ]
  • [ 1439-36-7 ]
  • ethyl (E)-4-oxo-2-propylpent-2-enoate [ No CAS ]
 

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