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Chemical Structure| 1214-47-7 Chemical Structure| 1214-47-7

Structure of 2'-Hydroxychalcone
CAS No.: 1214-47-7

Chemical Structure| 1214-47-7

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Product Details of [ 1214-47-7 ]

CAS No. :1214-47-7
Formula : C15H12O2
M.W : 224.25
SMILES Code : O=C(C1=CC=CC=C1O)C=CC2=CC=CC=C2
English Name :1-(2-Hydroxyphenyl)-3-phenylprop-2-en-1-one
MDL No. :MFCD00016441
InChI Key :AETKQQBRKSELEL-ZHACJKMWSA-N
Pubchem ID :638276

Safety of [ 1214-47-7 ]

Computational Chemistry of [ 1214-47-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 17
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 3
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 68.27
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.

2.32
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

3.89
Log Po/w (WLOGP)?

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

3.18
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.

2.78
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

3.45
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.12

Water Solubility

Log S (ESOL):?

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

-4.01
Solubility 0.0221 mg/ml ; 0.0000988 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.

-4.37
Solubility 0.00954 mg/ml ; 0.0000425 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

-4.38
Solubility 0.00924 mg/ml ; 0.0000412 mol/l
Class?

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

Moderately 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

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

Yes
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.

-4.91 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

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<2.0
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)

2.4

Application In Synthesis of [ 1214-47-7 ]

* 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 [ 1214-47-7 ]

[ 1214-47-7 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 1214-47-7 ]
  • [ 3516-95-8 ]
YieldReaction ConditionsOperation in experiment
98% With 10% Pd/C; hydrogen In dichloromethane at 20℃; for 6h;
97% With 10% Pd/C; diphenyl sulfide; hydrogen In methanol at 20℃; for 24h; chemoselective reaction;
95% With palladium 10% on activated carbon; hydrogen In ethanol for 0.5h;
90% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer In isopropyl alcohol at 130℃; for 12h; Inert atmosphere; Sealed tube; 2. Typical Procedure General procedure: To an oven-dried vial, chalcone 1 (0.20 mmol, 1.0 equiv), [(Cp*RhCl2)2] (0.006 mmol, 3.0 mol %), and isopropanol (1.0 mL) were added. The vial was charged with N2 and sealed immediately. The mixture was stirred at 100 °C, and the progress of the reaction was monitored by TLC. After the completion of the reaction, the mixture was cooled down to room temperature, filtered through a celite pad, and washed with ethyl acetate. The filtrate was concentrated in vacuo and the residue was purified by column chromatography on silica gel or preparative thin-layer chromatography to obtain the desired products 2 (petroleum ether : ethyl acetate = 100:1).
86% With formic acid In toluene at 120℃; for 20h; Inert atmosphere; chemoselective reaction;
86% With hydrogen; tetra-(n-butyl)ammonium iodide In water at 110℃; for 24h; chemoselective reaction;
86% With methanol; C25H29ClNO2Rh; potassium carbonate at 90℃; for 1h; chemoselective reaction; 2.2. Transfer hydrogenation of unsaturated ketones in methanol A Radley tube was charged with an unsaturated ketone (0.3mmol), catalyst (0.003 mmol) and K2CO3 (0.25 eq), to which was introduced MeOH (1.5 mL). The reaction mixture was heated to reflux at 90 °C for 1 h. The resulting mixture was then cooled to room temperature, followed by solvent evaporation under vacuum. The product was purified by flash column chromatography (hexane/ethyl acetate, 4:1).
86% With triethylsilane; 1,1,1,3',3',3'-hexafluoro-propanol; tris(pentafluorophenyl)borate at 40℃; for 1h; chemoselective reaction;
With lithium aluminium tetrahydride; aluminium trichloride In diethyl ether
801 mg With hydrogen In ethyl acetate for 0.166667h; Ambient temperature;
With hydrogen In ethyl acetate
172 mg With Yarrowia lipolytica KCh 71 In water; acetone at 25℃; for 72h; Microbiological reaction; enantioselective reaction; 2.3 Screening procedure General procedure: Erlenmeyer flasks (300ml), each containing 100ml of the medium consisting of 3g glucose and 1g aminobac dissolved in water, were inoculated with a suspension of microorganisms and then incubated for 3-7 days at 25°C on a rotary shaker (190rpm). After full growth of the culture 20mg of a substrate dissolved in 1ml of acetone was added. After 1, 3, 7, 12h and 1, 3, 6, 9 days of incubation under the above conditions, portions of 10ml of the transformation mixture were taken out and extracted with CHCl3 (3×10ml). The extracts were dried over MgSO4, concentrated in vacuo and analyzed by GC. All the experiments were repeated three times.
With 10% Pd/C In methanol at 20℃; for 0.5h;
Multi-step reaction with 2 steps 1: potassium hydroxide; <i>L</i>-proline / water / 20 °C 2: Penicillium raistrickii CBMAI 931 / aq. phosphate buffer / 168 h / 32 °C / pH 7
96 % With 10% Pd/C; ammonium formate In tetrahydrofuran at 40℃; 1-2 The compound of formula II (22.4g) was added in tetrahydrofuran (112ml), ammonium formate (12.6g) was added, and 10% palladium carbon (2.2g) was added, and the temperature was raised to 40°C for reaction. After the reaction was monitored by TLC, the palladium was removed by filtration Carbon and ammonium formate (can be reused many times after palladium carbon treatment); the filtrate is concentrated and evaporated to remove the solvent, isopropanol (100ml) is added, the temperature is raised to reflux, and after 30 minutes of heat preservation and reflux, cooling and crystallization begins. After crystallization at °C for 2 hours, the compound of formula I was obtained by filtration and drying, with a yield of 96% and an HPLC purity of 99.6%.

References: [1]Soto, Martín; Soengas, Raquel G.; Rodríguez-Solla, Humberto [Advanced Synthesis and Catalysis, 2020, vol. 362, # 23, p. 5422 - 5431].
[2]Location in patent: experimental part Mori, Akinori; Mizusaki, Tomoteru; Kawase, Masami; Maegawa, Tomohiro; Monguchi, Yasunari; Takao, Shinobu; Takagi, Yukio; Sajikia, Hironao [Advanced Synthesis and Catalysis, 2008, vol. 350, # 3, p. 406 - 410].
[3]Gupte, Amol; Buolamwini, John K. [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 3, p. 917 - 921].
[4]Yu, Xuewen; Wan, Saihong; Zhou, Wang [Synlett, 2022, vol. 34, # 12, p. 1399 - 1402].
[5]Song, Tao; Duan, Yanan; Yang, Yong [Catalysis Communications, 2019, vol. 120, p. 80 - 85].
[6]Song, Tao; Ma, Zhiming; Yang, Yong [ChemCatChem, 2019, vol. 11, # 4, p. 1313 - 1319].
[7]Aboo, Ahmed H.; Begum, Robina; Zhao, Liangliang; Farooqi, Zahoor H.; Xiao, Jianliang [Cuihua Xuebao/Chinese Journal of Catalysis, 2019, vol. 40, # 11, p. 1795 - 1799].
[8]Zhan, Xiao-Yu; Zhang, Hua; Dong, Yu; Yang, Jian; He, Shuai; Shi, Zhi-Chuan; Tang, Lei; Wang, Ji-Yu [Journal of Organic Chemistry, 2020, vol. 85, # 10, p. 6578 - 6592].
[9]Hase,T. [Acta Chemica Scandinavica (1947), 1968, vol. 22, p. 2845 - 2850].
[10]Murphy, William S.; Wattanasin, Sompong [Journal of the Chemical Society. Perkin transactions I, 1980, p. 1567 - 1577].
[11]Tanaka, Toshiyuki; Asai, Fujio; Iinuma, Munekazu [Phytochemistry, 1998, vol. 49, # 1, p. 229 - 232].
[12]Janeczko, Tomasz; Gladkowski, Witold; Kostrzewa-Suslow, Edyta [Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 98, p. 55 - 61].
[13]Gomes, Kaio S.; da Costa-Silva, Thais A.; Oliveira, Igor H.; Aguilar, Andrea M.; Oliveira-Silva, Diogo; Uemi, Miriam; Silva, Wender A.; Melo, Lennine R.; Andrade, Carlos Kleber Z.; Tempone, Andre G.; Baldim, João L.; Lago, João Henrique G. [Bioorganic and Medicinal Chemistry Letters, 2019, vol. 29, # 12, p. 1459 - 1462].
[14]de Matos, Iara L.; Birolli, Willian G.; Santos, Darlisson de A.; Nitschke, Marcia; Porto, André Luiz M. [Molecular catalysis, 2021, vol. 513].
[15]Current Patent Assignee: SHANDONG KEYUAN PHARMACEUTICAL - CN115124409, 2022, A Location in patent: Paragraph 0036; 0039; 0040; 0043.
  • 2
  • [ 1214-47-7 ]
  • [ 574-12-9 ]
  • 3
  • [ 55386-79-3 ]
  • [ CAS Unavailable ]
  • [ 18398-73-7 ]
  • [ 91137-41-6 ]
  • [ 22084-15-7 ]
  • [ 862197-80-6 ]
  • [ 487-26-3 ]
  • [ 1214-47-7 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1,3-dioxo-1-(2-hydroxyphenyl)butyl methyl ester; N-Benzylidenemethylamine In ethanol at 30 - 35℃; for 0.5h; Stage #2: With acetic acid In ethanol for 0.5h; Reflux;
  • 4
  • [ 1095-03-0 ]
  • (S)-3,3'-dibromo-1,1'-bi-2-naphthol [ No CAS ]
  • [ 1214-47-7 ]
  • C35H21BBr2O4 [ No CAS ]
  • 5
  • [ 16619-29-7 ]
  • [ 1214-47-7 ]
  • [ 2408256-05-1 ]
YieldReaction ConditionsOperation in experiment
95% With tetrabutylammomium bromide; potassium hydroxide In toluene at 45℃; 1 Preparation of 3-(3-oxo-1-(3-methylphenyl)-3-phenylpropyl)-flavanone (D) Weigh o-hydroxychalcone (0.10 mmol), 3-(3-methylphenyl)chalcone (0.15 mmol),Potassium hydroxide (0.03 mmol) and tetrabutylammonium bromide (0.01 mmol) were added to the reaction flask.1 mL of toluene was added, and the reaction was stirred at 45 ° C, and the reaction was detected by thin layer chromatography until the consumption of the starting material was complete.Cool to room temperature, add 5 mL of water to dissolve the solid, then add ethyl acetate to extract the mixture.The organic phase was dried over anhydrous sodium sulfate.The obtained crude product was subjected to silica gel column chromatography to obtain the pure product of the 3-substituted flavanone compound D.The yield was 95%.
 

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