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Structure of Phthalaldehyde
CAS No.: 643-79-8
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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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 |
GHS Pictogram: |
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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: | Ⅱ |
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 |
34.14 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.04 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.16 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.31 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.77 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
2.14 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.28 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.71 |
Solubility | 2.59 mg/ml ; 0.0193 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.47 |
Solubility | 4.53 mg/ml ; 0.0337 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.26 |
Solubility | 0.735 mg/ml ; 0.00548 mol/l |
Class? Solubility class: Log S scale |
Soluble |
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) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.29 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.0 |
* 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.
Yield | Reaction Conditions | Operation 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). |
Yield | Reaction Conditions | Operation 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). |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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. |
Yield | Reaction Conditions | Operation 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%). |