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Chemical Structure| 643-79-8 Chemical Structure| 643-79-8

Structure of Phthalaldehyde
CAS No.: 643-79-8

Chemical Structure| 643-79-8

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Product Details of [ 643-79-8 ]

CAS No. :643-79-8
Formula : C8H6O2
M.W : 134.13
SMILES Code : O=CC1=CC=CC=C1C=O
MDL No. :MFCD00003335
InChI Key :ZWLUXSQADUDCSB-UHFFFAOYSA-N
Pubchem ID :4807

Safety of [ 643-79-8 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H301-H314-H317-H335-H410
Precautionary Statements:P260-P264-P270-P271-P272-P273-P280-P301+P310+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P333+P313-P362+P364-P391-P403+P233-P405-P501
Class:8(6.1)
UN#:2923
Packing Group:

Computational Chemistry of [ 643-79-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 37.22
TPSA ?

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

34.14 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.04
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

1.16
Log Po/w (WLOGP)?

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

1.31
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.

0.77
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

2.14
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.28

Water Solubility

Log S (ESOL):?

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

-1.71
Solubility 2.59 mg/ml ; 0.0193 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.

-1.47
Solubility 4.53 mg/ml ; 0.0337 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

-2.26
Solubility 0.735 mg/ml ; 0.00548 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.

-6.29 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

1.0
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)

1.0

Application In Synthesis of [ 643-79-8 ]

* 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 [ 643-79-8 ]

[ 643-79-8 ] Synthesis Path-Downstream   1~13

  • 1
  • [ 613-73-0 ]
  • [ 643-79-8 ]
  • [ 98366-43-9 ]
  • [ 93657-18-2 ]
  • 2
  • [ 643-79-8 ]
  • [ 5234-26-4 ]
  • [ 60025-28-7 ]
  • 3
  • [ 22838-46-6 ]
  • [ 643-79-8 ]
  • [ 1174169-23-3 ]
YieldReaction ConditionsOperation in experiment
83% In dichloromethane; for 2h;Reflux; Acidic conditions; Step D: 3-Amino-3-phenyl-propionic acid methyl ester hydrochloride (1.3 mmol, 1 eq), benzene-1 ,2-dicarbaldehyde (0.8 eq) and glacial acid (15 eq) are dissolved in dichloromethane and refluxed for 2 h (J. Chem. Soc, Chem Commun 1985, 1183). The mixture is concentrated in vacuo and partitioned between dichloromethane and water. The organic phase is dried over Na2SO4, filtered and concentrated in vacuo. 3-(1-Oxo-1 ,3-dihydro-isoindole-2-yl)-3- phenyl-propionic acid methyl ester is obtained as a brown solid (83 % yield); ES-MS (MH+) = 296.2; 1H-NMR (DMSO-d6, 400 MHz): delta [ppm] 7.73-7.30 (m, <n="45"/>9H)1 5.82-5.78 (m, 1 H) 4.54 (d, 1 H, 17.4Hz), 4.14 (d, 1 H, 17.4Hz), 3.57 (s, 3H), 3.31-3.28 (m, 2H).
  • 4
  • [ 636-58-8 ]
  • [ 643-79-8 ]
  • [ 1282511-37-8 ]
  • 5
  • [ 102735-53-5 ]
  • [ 643-79-8 ]
  • [ 1407232-78-3 ]
  • 6
  • [ 102735-53-5 ]
  • [ 643-79-8 ]
  • [ 1407232-79-4 ]
YieldReaction ConditionsOperation in experiment
30% In acetonitrile; for 18h;Reflux; Inert atmosphere; Example 10(S)-3-Cyclopropyl-N-[1-(2-methoxy-2-methyl-propyl)-1H-pyrazol-3-yl]-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionamideA solution of benzene-1,2-dicarbaldehyde (340 mg, 2.55 mmol) and (S)-2-amino-3-cyclopropyl-propionic acid (300 mg, 2.32 mmol) in acetonitrile (15 mL) was heated to reflux for 18 h.The solution was cooled, concentrated and the residue redissolved in methylene chloride (50 mL).The solution was extracted with a saturated sodium bicarbonate solution.The layers were separated and the aqueous phase was acidified (pH=2) with hydrochloric acid (3N), extracted with methylene chloride (2*50 mL).The organic phases were combined, dried over magnesium sulfate, filtered and evaporated to give (S)-3-cyclopropyl-2-(1-oxo-1,3-dihydro-isoindol-2-yl)-propionic (170 mg, 30percent) as a yellow solid: LR-ES(+) m/e calcd for C14H15NO3 [M+H]+ 246.29, observed 246.2; 1H NMR (DMSO-d6) delta7.24-7.94 (m, 4H), 4.83 (dd, J=10.6, 4.8 Hz, 1H), 4.54 (s, 2H), 3.16 (d, J=3.6 Hz, 1H), 1.90-2.16 (m, 1H), 1.54-1.79 (m, 1H), 0.65 (dd, J=7.8, 5.4 Hz, 1H), 0.29-0.48 (m, 2H), -0.01-0.19 (m, 2H).
  • 7
  • [ 643-79-8 ]
  • [ 479-79-8 ]
  • 8
  • [ 7677-24-9 ]
  • [ 36340-61-1 ]
  • [ 643-79-8 ]
  • [ 1575389-16-0 ]
YieldReaction ConditionsOperation in experiment
65% In acetonitrile; for 12.0h;Reflux; General procedure: A mixture of a 2-aminopyridine (1 mmol), phthalaldehyde (2) (1 mmol), and TMSCN (3)(1 mmol) in CH3CN (10 mL) was refluxed for the appropriate amount of time.After completion of the reaction, as indicated by TLC (EtOAc/n-hexane, 4:1), themixture was filtered and the residue purified by washing with n-hexane(5 mL), and then crystallized from EtOH or CH3CN to give pure crystallineproducts 4a-i.
  • 9
  • [ 32249-35-7 ]
  • [ 643-79-8 ]
  • 3-(1-cyclopropyl-3-methoxy-1,3-dioxopropan-2-yl)-1,3-dihydro-2-benzofuran-1-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
73% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate; In tetrahydrofuran;Schlenk technique; Reflux; General procedure: A Schlenk tube was charged with dialdehyde 1 (0.100 mmol), [Cp*RhCl2]2 (2.0 μmol, 2 mol % dimer, 4 mol % Rh), Cu(OAc)2 (0.150 mmol), and then THF (1.0 mL) and 1,3-dicarbonyl compound 8 (0.200 mmol) were added. The mixture was heated at reflux under air. The reaction mixture was filtered through a plug of Florisil washing with hexane-AcOEt, and the filtrate was concentrated. The residue was purified by preparative TLC on silica gel to afford the following compounds.
  • 10
  • [ 3081-61-6 ]
  • [ 937-00-8 ]
  • [ 643-79-8 ]
  • C22H21F3N2O3S [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; water; at 20℃; for 0.0166667h; An aqueous solution of <strong>[3081-61-6]theanine</strong> was added to 50 mM sodium borate buffer solution (50 muL)(1 mM, 50 muL), ethanol solution of fluorinated thiol (100 mM, 50 muL)And ethanol solution of ortho-phthalaldehyde (OPA) (100 mM, 25 muL)And the mixture was reacted at room temperature for 1 minute.
  • 11
  • [ 7292-74-2 ]
  • [ 643-79-8 ]
  • C16H12FNO3 [ No CAS ]
  • 12
  • [ 16313-65-8 ]
  • [ 643-79-8 ]
  • 3-nitroisoindolo[2,1-a]quinazolin-5(11H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With hydrogenchloride; In methanol; at 20℃; for 24h; General procedure: A mixture ofanthranilamide (340 mg, 2.50 mmol), and o-phthalaldehyde(334.9 mg, 2.50 mmol) were taken in100 mL round bottom flask. Then to this reactionmixture, 30 mL MeOH and 2(N) HCl (10 mL) wereadded. This reaction mixture was stirred at roomtemperature for 24 h. Then, the precipitate appearedwas collected by filtration and washed with water toget 3aHCl (411 mg, 70%).
  • 13
  • [ 23069-99-0 ]
  • [ 643-79-8 ]
  • [ 34493-83-9 ]
 

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