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Structure of 3-Cyanochromone
CAS No.: 50743-17-4

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Quality Control of [ 50743-17-4 ] Purity: 98% SDS Specification

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Product Details of [ 50743-17-4 ]

CAS No. :	50743-17-4
Formula :	C₁₀H₅NO₂
M.W :	171.15
SMILES Code :	O=C1C(C#N)=COC2=C1C=CC=C2
English Name :	4-Oxo-4H-chromene-3-carbonitrile
MDL No. :	MFCD00052604
InChI Key :	SFWNPLLGXKJESA-UHFFFAOYSA-N
Pubchem ID :	521298

Safety of [ 50743-17-4 ]

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Computational Chemistry of [ 50743-17-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	10
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	3.0
Num. H-bond donors	0.0
Molar Refractivity	47.2
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	54.0 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.62
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.47
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.66
Log P_o/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.	0.18
Log P_o/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	2.41
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.47

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.4
Solubility	0.687 mg/ml ; 0.00401 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.21
Solubility	1.05 mg/ml ; 0.00616 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	-3.69
Solubility	0.0348 mg/ml ; 0.000203 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.	-6.3 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	0.0 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)	2.69

Application In Synthesis of [ 50743-17-4 ]

* 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 [ 50743-17-4 ]

[ 50743-17-4 ] Synthesis Path-Downstream 1~14

1
[ 50743-17-4 ]
[ 50743-45-8 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminium trichloride; sodium azide In tetrahydrofuran
86 %	With sodium azide In water at 80℃;	1H-Tetrazoles 2a-z; General Procedure General procedure: (CAUTION Sodium azide can explode on heating and is highlytoxic. Contact of metal azides with acids liberates highly toxicand explosive hydrazoic acid.)NH4N3 (0.5 mmol) and H2SO4 (0.5 mmol) were added sequentiallyto a round-bottomed flask containing the appropriatealdehyde (0.5 mmol) in EtOH (1 mL), and the resulting mixturewas stirred at r.t. for 10 min. A solution of NaN3 (0.5 mmol) inH2O (1 mL) was then added, and the resulting mixture wasstirred for another 2 h at 80 °C. When the starting material hadbeen consumed, the mixture was cooled to r.t. and ice-cold H2Owas added to give a solid precipitate. The precipitate was collectedand washed with 20% CH2Cl2-hexane to give the pureproduct.

References: [1]Nohara,A. et al. [Journal of Medicinal Chemistry, 1977, vol. 20, # 1, p. 141 - 145].
[2]Singh, Rajeev; Ahmed, Naseem [Synlett, 2024, vol. 36, # 8, p. 1003 - 1008].

2
[ 50743-17-4 ]
[ 61424-76-8 ]

Yield	Reaction Conditions	Operation in experiment
88%	With ammonium hydroxide In lithium hydroxide monohydrate at 20℃;	General Procedure for the Synthesis of 1[1]. General procedure: A mixture of substritued 4-oxo-4H-1-benzopyran-3-carbonitriles (10 mmol) and concentratedNH4OH solution (10 mL) was stirred at room temperature until the solid dissolved and then wasdiluted with water (10 mL). The product obtained was filtered and recrystallized from ethanol togive 1 as yellow crystals. The compounds have been reported [2] and the 1H and 13C data aresupplemented as follows.
70%	With morpholine; lithium hydroxide monohydrate In N,N-dimethyl-formamide at 60℃; for 2h;
70%	With morpholine; lithium hydroxide monohydrate In N,N-dimethyl-formamide at 60℃; for 2h;

42%	With aluminum(III) oxide In dichloromethane for 8h; Ambient temperature;
	Multi-step reaction with 2 steps 1: 70 percent / ethylenediamine / ethanol / 0.17 h / Heating 2: 73 percent / acetic acid / 0.5 h / Heating

References: [1]Yang, Hongchen; Zhang, Lu; Xu, Xiaoyong; Shao, Xusheng; Li, Zhong [Synlett, 2022, vol. 33, # 8, p. 754 - 758].
[2]Ishiguro, Toshihiro; Ukawa, Kiyoshi; Sugihara, Hirosada; Nohara, Akira [Heterocycles, 1981, vol. 16, # 5, p. 733 - 740].
[3]Nohara; Ishiguro; Ukawa; Sugihara; Maki; Sanno [Journal of Medicinal Chemistry, 1985, vol. 28, # 5, p. 559 - 586].
[4]Ghosh, Chandra Kanta; Bhattacharyya, Samita; Ghoshal, Nanda; Achari, Basudeb [Journal of Chemical Research, Miniprint, 1998, # 4, p. 859 - 869].
[5]Ghosh, Chandra Kanta; Tewari, Nimai; Bandyopadhyay, Chandrakanta [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 12, p. 1200 - 1204].

3
[ 118-93-4 ]
[ 68-12-2 ]
[ 50743-17-4 ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: o-hydroxyacetophenone; N,N-dimethyl-formamide With trichlorophosphate at 0 - 25℃; for 4h; Stage #2: With hydroxylamine hydrochloride In dichloromethane at 5 - 25℃; for 6h;	Chromone-3-carbonitrile (10a) 2-hydroxyacetophenone 1 (3.4 mL, 28.24 mmol) in DMF (15.5 mL, 200 mmol) was cooled to 0 °C and POCl3 (9.3 mL, 100 mmol) was gradually added to the solution. The mixture was stirred at room temperature for 4 h and then a solution of NH2OH.HCl (5.22 g, 75 mmol) in DCM (34 mL) added to the reaction mixture at 5 °C. The resulting mixture was then stirred for 6 h at room temperature and quenched with water (30 mL); extracted with DCM (3 x 25 mL), washed with water (1 x 10 mL), washed with saturated NaHCO3 solution (1 x 10 mL) and dried over Na2SO4. The solution was concentrated under reduced pressure to give a crude solid, which was directly recrystallized from methanol to afford chromone-3-carbonitrile 10a (3.8 g, 78 %) as pale yellow solid; mp174-176°C (lit.,13 175-177 °C; IR νmax/cm-13083 (CH), 2239. (CN), 1658. (C=O);1H NMR δH (400 MHz, DMSO-d6) 7.60 (1H, dt, J 7.2 and 8.8 Hz, 8-H), 7.76 (1H, d, J 8.8 Hz, H-6), 7.91 (1H, m, 7-H), 8.08 (1H, dd, J 1.2 and 7.2 Hz, 5-H), 9.26 (1H,s, 2-H); δC (100 MHz, DMSO-d6) 165.86 (C-2), 101.49 (C-3), 172.99 (C-4), 123.12 (C-4a), 127.54 (C-5), 125.56 (C-6), 136.09 (C-7), 119.33 (C-8), 155.82 (C-8a) and 113.66 (CN); Anal. Calc. for C10H5NO2; C 70.18; H 2.94; N 8.18. Found: C 69.09; H 2.75: N 7.95.
68%	Stage #1: o-hydroxyacetophenone; N,N-dimethyl-formamide With trichlorophosphate at 20 - 80℃; for 0.351667h; Inert atmosphere; Stage #2: With hydroxylamine hydrochloride at 80℃; for 0.13h; Inert atmosphere; Sonication;
61%	Stage #1: o-hydroxyacetophenone; N,N-dimethyl-formamide With trichlorophosphate at 0 - 20℃; for 4h; Stage #2: N,N-dimethyl-formamide With hydroxylamine hydrochloride In dichloromethane at 20℃; for 4h; Further stages.;

	Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 0.5h; Stage #2: o-hydroxyacetophenone at 0 - 20℃; for 4h; Stage #3: With hydroxylamine hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;
	Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 0.5h; Stage #2: o-hydroxyacetophenone at 0 - 20℃; for 4h; Stage #3: With hydroxylamine hydrochloride at 0 - 20℃;
	Stage #1: N,N-dimethyl-formamide With trichlorophosphate Inert atmosphere; Stage #2: o-hydroxyacetophenone at 0 - 20℃; Inert atmosphere; Stage #3: With hydroxylamine hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere;
	Stage #1: N,N-dimethyl-formamide With trichlorophosphate at 0℃; for 0.5h; Stage #2: o-hydroxyacetophenone at 20℃; for 4h; Stage #3: With hydroxylamine hydrochloride In dichloromethane at 20℃;	2.1 General procedure for the synthesis of 3-cyanochromones General procedure: A mixture of dimethylformamide (80 mmol, 8.0 equiv.) and phosphorus oxychloride(40 mmol, 4.0 equiv.) were stirred at 0 °C for 30 min. To this solution, 2-hydroxyacetophenone (10 mmol, 1.0 equiv.) was added dropwise at 0 °C. The mixture was stirred at room temperature for 4 h. After completion of the reaction, as indicatedby TLC, the reaction mixture was diluted with dichloromethane (40 mL). The mixture was cooled to 0 °C and hydroxylamine hydrochloride (30 mmol, 3.0 equiv.) in DMF(10 mL) was then added. The resulting mixture was stirred at room temperature and thereaction progress was monitored by TLC. After completion of the reaction, the mixturesolution was diluted with cold water (100 mL) and extracted with DCM (3 × 50 mL). The combined organic phases were washed with saturated NaHCO3 solution (10 mL)and water (50 mL). The combined extracts were dried over anhydrous Na2SO4. Thesolvent was removed in vacuo and the residual solid was purified via flash chromatography or recrystallization to give the desired produces. All of the desired products are known compounds and the characterization data are in agreement withthose reported in the literature.

References: [1]Gordon, Allen T.; Ramaite, Isaiah D.I.; Mnyakeni-Moleele, Simon S. [Arkivoc, 2020, vol. 2020, # 5, p. 148 - 160].
[2]Pellegatti, Laurent; Buchwald, Stephen L. [Organic Process Research and Development, 2012, vol. 16, # 8, p. 1442 - 1448].
[3]Jagath Reddy; Latha; Thirupathaiah; Srinivasa Rao [Tetrahedron Letters, 2004, vol. 45, # 4, p. 847 - 848].
[4]Meng, Ling; Chang, Xiaoyong; Lin, Zhenyang; Wang, Jun (Joelle) [Organic and Biomolecular Chemistry, 2021, vol. 19, # 12, p. 2663 - 2667].
[5]Meng, Ling; Liu, Heyang; Lin, Zhenyang; Wang, Jun [Organic Letters, 2022, vol. 24, # 32, p. 5890 - 5895].
[6]Li, Qiaoqiang; Dai, Yuqing; Xu, Xinru; Wu, Wentao; Chen, Wenchao; Wang, Hong; Tan, Choon-Hong; Ye, Xinyi [Organic Letters, 2024, vol. 26, # 29, p. 6241 - 6246].
[7]Wang, Ke-Hu; Liang, Xiuwen; Luo, Wenjing; Chen, Maizhuo; Wang, Junjiao; Huang, Danfeng; Hu, Yulai [Synthesis (Germany), 2024, vol. 56, # 22, p. 3475 - 3487].

4
[ 17422-74-1 ]
[ 50743-17-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	With hydroxylamine hydrochloride In acetonitrile for 2h; Heating;
	With formic acid; hydroxylamine hydrochloride; sodium formate In water	10 4-Oxo-4H-1-Benzopyran-3-carbonitrile EXAMPLE 10 SPC21 4-Oxo-4H-1-Benzopyran-3-carbonitrile A mixture of 26.1 g. (0.15 mole) of 4-oxo-4H-1-benzopyran-3-carboxaldehyde, 13.1 g. (0.19 mole) of hydroxylamine hydrochloride, 18.4 g. (0.27 mole) of sodium formate and 250 ml of 99% formic acid was heated with stirring at reflux for 21/2 hours. Water was added to 1-liter volume. The separated solid was filtered from the cooled mixture, washed well with water and dried to give 13 g. (51%) of crude nitrile melting at 138°-145°C. Recrystallization from ethylacetate gave pure, white crystals melting at 174°-176°. Anal. Calcd for C10 H5 NO2: C, 70.17; H, 2.94; N, 8.18. Found: C, 70.18; H, 3.05; N, 8.22.
	With ammonium azide; sulfuric acid In ethanol at 30℃;	1H-Tetrazoles 2a-z; General Procedure General procedure: (CAUTION Sodium azide can explode on heating and is highlytoxic. Contact of metal azides with acids liberates highly toxicand explosive hydrazoic acid.)NH4N3 (0.5 mmol) and H2SO4 (0.5 mmol) were added sequentiallyto a round-bottomed flask containing the appropriatealdehyde (0.5 mmol) in EtOH (1 mL), and the resulting mixturewas stirred at r.t. for 10 min. A solution of NaN3 (0.5 mmol) inH2O (1 mL) was then added, and the resulting mixture wasstirred for another 2 h at 80 °C. When the starting material hadbeen consumed, the mixture was cooled to r.t. and ice-cold H2Owas added to give a solid precipitate. The precipitate was collectedand washed with 20% CH2Cl2-hexane to give the pureproduct.

References: [1]Jagath Reddy; Latha; Thirupathaiah; Srinivasa Rao [Organic Preparations and Procedures International, 2004, vol. 36, # 3, p. 287 - 289].
[2]Current Patent Assignee: WARNER LAMBERT LLC - US3937837, 1976, A.
[3]Singh, Rajeev; Ahmed, Naseem [Synlett, 2024, vol. 36, # 8, p. 1003 - 1008].

5
[ 910451-61-5 ]
[ 50743-17-4 ]
[ 910451-85-3 ]

Yield	Reaction Conditions	Operation in experiment
88%	In tetrahydrofuran at 20℃; for 12h;

References: [1]Patil, Nitin T.; Huo, Zhibao; Yamamoto, Yoshinori [Journal of Organic Chemistry, 2006, vol. 71, # 18, p. 6991 - 6995].

6
[ 910451-59-1 ]
[ 50743-17-4 ]
[ 910451-83-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	In tetrahydrofuran at 20℃; for 12h;

References: [1]Patil, Nitin T.; Huo, Zhibao; Yamamoto, Yoshinori [Journal of Organic Chemistry, 2006, vol. 71, # 18, p. 6991 - 6995].

7
[ 865876-51-3 ]
[ 50743-17-4 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
78%	With tetra-(n-butyl)ammonium iodide; triphenylphosphine In tetrahydrofuran at 40℃; for 18h;

References: [1]Knight, Julian G.; Stoker, Paul A.; Tchabanenko, Kirill; Harwood, Simon J.; Lawrie, Kenneth W.M. [Tetrahedron, 2008, vol. 64, # 17, p. 3744 - 3750].

8
[ 455-19-6 ]
[ 50743-17-4 ]
[ 1380762-56-0 ]