Home Cart Sign in  
Chemical Structure| 15174-69-3 Chemical Structure| 15174-69-3

Structure of 15174-69-3

Chemical Structure| 15174-69-3

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 15174-69-3 ]

CAS No. :15174-69-3
Formula : C8H8O2
M.W : 136.15
SMILES Code : C1=C(C(=CC=C1C=O)O)C
MDL No. :MFCD00012360
InChI Key :BAKYASSDAXQKKY-UHFFFAOYSA-N
Pubchem ID :139901

Safety of [ 15174-69-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 15174-69-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 10
Num. arom. heavy atoms 6
Fraction Csp3 0.12
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 38.82
TPSA ?

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

37.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.36
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

0.73
Log Po/w (WLOGP)?

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

1.51
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.

1.12
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

1.96
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.34

Water Solubility

Log S (ESOL):?

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

-1.52
Solubility 4.09 mg/ml ; 0.0301 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.

-1.09
Solubility 11.0 mg/ml ; 0.0809 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

-2.13
Solubility 1.02 mg/ml ; 0.00746 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

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.

-6.61 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 [ 15174-69-3 ]

* 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 [ 15174-69-3 ]

[ 15174-69-3 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 15174-69-3 ]
  • [ 18299-15-5 ]
YieldReaction ConditionsOperation in experiment
To a solution [OF 4-HYDROXY-3-METHYLBENZALDEHYDE (10G,] 73.5 [MMOL)] in dry [CH2CI2] (550 mL) under nitrogen at [5C] was added tetra-N-butylammonium borohydride (20.58 g, 80 [MMOL)] and the resultant mixture stirred for 1.25 h at [5C.] Saturated ammonium chloride solution (30 mL) was added to the reaction mixture and the resultant mixture stirred for 1 h at [5C.] Saturated ammonium chloride solution (60 mL) was added and the reaction mixture extracted with [CH2CI2,] dried [(NA2SO4)] and the solvents removed in vacuo. Purification by flushing through silica (2 x 150 g) eluting with EtOAc afforded the title compound as an oily yellow solid (8.01 g). [1H] NMR (400 MHz; [MEOH-D4)] 8 : 2.19 (3H, s), 4.46 (2H, s), 6.71 [(1H, D,] J 8Hz), 6.99 [(1H,] dd, J 8Hz, 2Hz), 7.06 (1 H, d, J 2Hz), OH not observed.
  • 2
  • [ 15174-69-3 ]
  • [ 15777-70-5 ]
YieldReaction ConditionsOperation in experiment
66% With hydroxylamine hydrochloride; acetic acid; for 1.5h;Heating / reflux; Preparation 70: 4-Hydroxy-3-methylbenzonitrile A mixture of 4-hydroxy-3-methylbenzaldehyde (530 mg, 3.91 mmol) and hydroxyl ammonium chloride (406 mg, 5.81 mmol) in acetic acid (5 mL) was heated under reflux for 90 minutes. The cooled reaction mixture was then diluted with diethyl ether (30 mL) and washed with water (30 mL). The combined organic solution was washed with brine, dried over magnesium sulfate, concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol, 100:0 to 97.5:2.5, to afford the title compound as a pale yellow oil in 66% yield, 345 mg. 1H NMR(400 MHz, CDCl3) δ: 2.25(s, 3H), 6.84(d, 1H), 7.37(d, 1H), 7.40(s, 1H)
  • 3
  • [ 15174-69-3 ]
  • [ 34956-31-5 ]
  • [ 1076188-42-5 ]
YieldReaction ConditionsOperation in experiment
[00607] To a mixture of <strong>[34956-31-5]N-(4-acetyl-3-methylphenyl)acetamide</strong> (1.3g, 7.0 mmol) and NaOH (1.4 g, 36 mmol) in 25 mL of absolute EtOH was added 4-hydroxy-3-methylbenzaldehyde (1.0 g, 7.3 mmol). The reaction mixture was stirred at room temperature for 18 hr. 5 mL of water was added and the reaction mixture was acidified with concentrated HCl to pH 5-6. The aqueous layer was extracted with two 25 mL portions of EOAc, and the layers were separated. The organic layer was dried with Na2SO4, filtered and concentrated under reduced pressure. The resulting product was submitted to the next step without further purification. MS (EI) for Ci9Hi9NO3: 310 (MH+).
  • 4
  • [ 15174-69-3 ]
  • [ 34956-31-5 ]
  • [ 1076188-17-4 ]
YieldReaction ConditionsOperation in experiment
55% [00248] To a round bottomed flask was added EtOH (30 mL) and potassium hydroxide (6.0 g, 109.5 mmol). The mixture was stirred until homogeneous before adding commercially available 4-hydroxy-3-methyl benzaldehyde (3.Og, 21.9 mmol) and commercially available 4- acetamido-2-methyl acetophenone (4.2 g, 21.9 mmol). The reaction was heated to 80 0C overnight, cooled to rt, and concentrated via rotary evaporation. The solid was dissolved in H2O and neutralized with IN HCl until pH =7. The aqueous mixture was extracted 5 X with EtOAc. The combined EtOAc layers were concentrated and column purified on silica gel (1 : 1 EtOAc: Hexanes) to afford (E)-I -(4-amino-2-methylphenyl)-3-(4-hydroxy-3-methylphenyl) prop-2-en-l -one (2) (3.1 g, 55% yield).1H NMR (400 MHz, d6-DMSO) δ 7.64 (dd, 2H), 7.37 (s, 2H), 6.81 (d, IH), 6.42 (m, 2H), 5.87 (d, 2H), 2.38 (d, 4H), 2.15 (s, 2H); MS (EI) for Ci7H17NO2: 268.2 (MH+).
  • 5
  • [ 62254-74-4 ]
  • [ 15174-69-3 ]
  • [ 1076188-34-5 ]
YieldReaction ConditionsOperation in experiment
00267) To a mixture of commercially available 4'-hydroxy-3'-methylacetophenone (700 mg, 4.66 mmol) and NaOH (365 mg, 9.1 mmol) in 10 mL of absolute EtOH was added commercially available 5-methylisoxazole-3-carbaldehyde (518 mg, 4.66 mmol). The reaction mixture was stirred at room temperature for 18 hr. 5 mL of water was added and the reaction mixture was acidified with concentrated HCI to pH 5-6. The precipitate was filtered, washed15 <n="117"/>with water and dried to give (E)-l-(4-hydroxy-3-methylphenyl)-3-(5-methylisoxazol-3- yl)prop-2-en-l-one. MS (EI) for Ci4H13NO3: 244 (MH+).
  • 6
  • [ 15174-69-3 ]
  • [ 78364-55-3 ]
  • 6-fluoro-2-(2-(4-hydroxy-3-methylbenzylidene)hydrazino)benzothiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% With acetic acid; In ethanol; at 80℃; for 0.166667h;Microwave irradiation; General procedure: A mixture of compound 2 (0.0549 g, 0.0003 mol), the appropriate aromatic aldehyde (0.00033 mol) and glacial acetic acid (0.1 mL) in ethanol (5 mL) was heated under microwave (20 W) at 80 °C for 10 min. On cooling, the precipitated solid was collected by filtration, washed with water, dried and crystallized to give compounds 3-29.
  • 8
  • [ 15174-69-3 ]
  • [ 18650-39-0 ]
  • methyl (S)-1-(4-hydroxy-3-methylbenzyl)piperidine-2-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium tris(acetoxy)borohydride; N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 20℃; To a solution of 4-hydroxy-3-methylbenzaldehyde (Aldrich cat316911: 400.0 mg, 2.938 mmol) and N,N-diisopropylethylamine (8.8 mmol) in 1,2-dichloroethane (200 mmol) was added <strong>[18650-39-0](S)-methyl piperidine-2-carboxylate hydrochloride</strong> (Combi-Blocks catSS-2950: 690 mg, 3.8 mmol) followed by sodium triacetoxyborohydride (1.9 g, 8.8 mmol). The mixture was stirred at room temperature overnight. The crude reaction mixture was diluted with DCM, then sequentially washed with an aqueous NaHCO3 solution, water, and brine. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude residue was purified by silica gel chromatography eluting with 40percent ethyl acetate in hexanes to give the desired product. LC-MS calculated for C15H22NO3 (M+H)+: m/z=264.2; found: 264.2.
 

Historical Records

Technical Information

• Acidity of Phenols • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Electrophilic Substitution of the Phenol Aromatic Ring • Etherification Reaction of Phenolic Hydroxyl Group • Fischer Indole Synthesis • Friedel-Crafts Reaction • Grignard Reaction • Halogenation of Phenols • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Oxidation of Phenols • Passerini Reaction • Paternò-Büchi Reaction • Pechmann Coumarin Synthesis • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Reimer-Tiemann Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

Related Functional Groups of
[ 15174-69-3 ]

Aryls

Chemical Structure| 613-84-3

A132681 [613-84-3]

2-Hydroxy-5-methylbenzaldehyde

Similarity: 0.97

Chemical Structure| 2233-18-3

A138338 [2233-18-3]

4-Hydroxy-3,5-dimethylbenzaldehyde

Similarity: 0.97

Chemical Structure| 18362-36-2

A157612 [18362-36-2]

6-Methylsalicylaldehyde

Similarity: 0.97

Chemical Structure| 85231-15-8

A163250 [85231-15-8]

4-Hydroxy-2,5-dimethylbenzaldehyde

Similarity: 0.97

Chemical Structure| 57295-30-4

A548351 [57295-30-4]

3-Hydroxy-4-methylbenzaldehyde

Similarity: 0.97

Aldehydes

Chemical Structure| 613-84-3

A132681 [613-84-3]

2-Hydroxy-5-methylbenzaldehyde

Similarity: 0.97

Chemical Structure| 2233-18-3

A138338 [2233-18-3]

4-Hydroxy-3,5-dimethylbenzaldehyde

Similarity: 0.97

Chemical Structure| 18362-36-2

A157612 [18362-36-2]

6-Methylsalicylaldehyde

Similarity: 0.97

Chemical Structure| 85231-15-8

A163250 [85231-15-8]

4-Hydroxy-2,5-dimethylbenzaldehyde

Similarity: 0.97

Chemical Structure| 57295-30-4

A548351 [57295-30-4]

3-Hydroxy-4-methylbenzaldehyde

Similarity: 0.97