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[ CAS No. 66521-54-8 ] {[proInfo.proName]}

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Chemical Structure| 66521-54-8
Chemical Structure| 66521-54-8
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Product Details of [ 66521-54-8 ]

CAS No. :66521-54-8 MDL No. :MFCD00115039
Formula : C10H12N2O Boiling Point : -
Linear Structure Formula :- InChI Key :BWERGHWJEBQNQV-SOFGYWHQSA-N
M.W : 176.22 Pubchem ID :5369159
Synonyms :

Calculated chemistry of [ 66521-54-8 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.2
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.27
TPSA : 33.2 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.52 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.13
Log Po/w (XLOGP3) : 1.21
Log Po/w (WLOGP) : 1.34
Log Po/w (MLOGP) : 0.12
Log Po/w (SILICOS-IT) : 1.27
Consensus Log Po/w : 1.21

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.84
Solubility : 2.56 mg/ml ; 0.0145 mol/l
Class : Very soluble
Log S (Ali) : -1.5
Solubility : 5.52 mg/ml ; 0.0313 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.17
Solubility : 1.19 mg/ml ; 0.00675 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.2

Safety of [ 66521-54-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 66521-54-8 ]

* 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.

  • Upstream synthesis route of [ 66521-54-8 ]
  • Downstream synthetic route of [ 66521-54-8 ]

[ 66521-54-8 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 1122-62-9 ]
  • [ 4637-24-5 ]
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YieldReaction ConditionsOperation in experiment
51% at 90℃; for 12 h; A solution of 4.0 g (33.0 mmol, 1.0 eq.) of 1-(pyridin-2-yl)ethan-1-one in 13.1 mL (99.1 mmol, 3.0 eq,) of DMF dimethylacetal was stirred at 90 °C for 12 h. The mixture wasallowed to cool to room temperature, and the resulting precipitate was collected by filtration. The solids were washed with 2 x 5 mL of ethyl acetate and dried under high vacuum to provide, 3.0 g (17.0 mmol, 51percent) of (E)-3 -(dimethylamino)- 1 -(pyridin-2-yl)prop-2-en- 1-one.
13 g for 24 h; Reflux 12.1 g of 2-acetylpyridine was dissolved in 150 ml of toluene, 30 ml of DMF-DMA was added while stirring, and the mixture was heated to reflux for 24 hours, cooled to room temperature, concentrated to dryness under reduced pressure, and 150 ml of petroleum ether was added to the residue for stirring. Disperse, filter, filter cake washed with petroleum ether to give intermediate 13g, yellow crystals.
Reference: [1] Molecules, 2007, vol. 12, # 8, p. 2061 - 2079
[2] European Journal of Organic Chemistry, 2012, # 32, p. 6407 - 6413,7
[3] Synthetic Communications, 1993, vol. 23, # 13, p. 1897 - 1903
[4] Organic Preparations and Procedures International, 1997, vol. 29, # 3, p. 285 - 292
[5] Journal of Chemical Research, Miniprint, 1997, # 3, p. 601 - 615
[6] Chemical Communications, 2017, vol. 53, # 91, p. 12286 - 12289
[7] Organic Letters, 2018, vol. 20, # 4, p. 1256 - 1260
[8] Journal of Heterocyclic Chemistry, 2007, vol. 44, # 2, p. 355 - 361
[9] European Journal of Organic Chemistry, 2016, vol. 2016, # 18, p. 3060 - 3064
[10] Tetrahedron Letters, 1999, vol. 40, # 26, p. 4779 - 4782
[11] Dalton Transactions, 2012, vol. 41, # 13, p. 3684 - 3694
[12] Patent: WO2018/172852, 2018, A1, . Location in patent: Page/Page column 204; 206
[13] European Journal of Organic Chemistry, 2005, # 17, p. 3775 - 3780
[14] Bioorganic and Medicinal Chemistry Letters, 1997, vol. 7, # 2, p. 187 - 192
[15] Synthesis, 2001, # 1, p. 55 - 62
[16] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 6, p. 1641 - 1645
[17] Patent: US5859215, 1999, A,
[18] Patent: US4788195, 1988, A,
[19] Patent: US4281000, 1981, A,
[20] European Journal of Inorganic Chemistry, 2013, # 24, p. 4305 - 4317
[21] Patent: CN103936792, 2017, B, . Location in patent: Paragraph 0093; 0094; 0095
  • 2
  • [ 1122-62-9 ]
  • [ 4637-24-5 ]
  • [ 98-86-2 ]
  • [ 1131-80-2 ]
  • [ 66521-54-8 ]
Reference: [1] Synthesis, 2011, # 12, p. 1930 - 1935
  • 3
  • [ 66521-54-8 ]
  • [ 75415-03-1 ]
YieldReaction ConditionsOperation in experiment
98% With hydrazine In ethanolHeating / reflux To a solution of 10 g (56. 7 mmol) of 3-dimethylamino-1-pyridin-2-yl- propenone in 100 mL absolute ethanol was added 1. 96 mL (62. 4 mmol, 1. 1 equiv.) of anhydrous hydrazine with stirring to give a pale yellow solution. This solution was heated to reflux and stirred overnight, then concentrated to give a tan-colored solid. The solid was then crystallized from ethyl acetate/hexane to give 8. 06 g (55. 5 mmol, 98percent) of 2-(1H-pyrazol-3-yl)-pyridine as tan-colored CRYSTALS. 1H-NMR (300 MHz, CDCI3, 8) : 11. 69 (br s, 1 H), 8. 66 (dd, J = 1 Hz, 5 Hz, 1 H), 7. 76 (d, J = 3 Hz, 1 H), 7. 74 (s, 1 H), 7. 66 (d, J = 2 Hz, 1 H), 7. 23 (t, J = 9 HZ, 1 H), 6. 81 (d, J = 3 Hz, 1 H) ; M/Z : 146 [M + H] +.
0.19 g at 50℃; for 0.166667 h; Microwave irradiation Its synthesis by conventional methods and some spectroscopic datahave been previously reported [15a,15b]. MW assisted method: A mixtureof 2-acetylpyridine (0.22 mL, 2 mmol) and DMF-dimethylacetal(0.27 mL, 2 mmol) was heated in a microwave oven for 2 h at 100 °C,and then the volatiles were removed in vacuo. The brown red solid wasmixed with hydrazine hydrate (0.2 mL, 4 mmol) and heated in a microwaveoven for 10 min at 50 °C. The volatiles were removed in vacuo,the red residue was washed with water (3×5 mL), and the ochre solidthus obtained was dried in vacuo, and recrystallized from CH2Cl2/hexane, yielding 0.19 g (65percent). IR (cm−1): 3124 m, 3058 m, 3023 m,2978 m, 2937 m, 2898 m, 2835 m, 2802 m, 2735 m, 2654 w, 2501 w,2324 w, 2165 w, 2051 w, 1981 w, 1704 w, 1590 s, 1567 m, 1536 w,1502 m, 1454 m, 1416 s, 1357 m, 1303 m, 1271 w, 1231 m, 1192 w,1144 m, 1129 w, 1088 m, 1059 m, 1048 m, 1036 w, 1000 w, 993 m,950 m, 924 w, 877 m, 843 m, 797 m, 757 vs, 704 s, 695 m, 627 m,615 m. 1H NMR (400 MHz, CDCl3) δ 11.70 (s, NH, 1H), 8.63 (dt, J=4.9and 1.2 Hz, H3′, 1H), 7.73 (dt, J=8.2 and 4.1 Hz, H6′ and H4′, 2H), 7.64(d, J=2.1 Hz, H4, 1H), 7.22 (dd, J=8.1, 4.9 Hz, H5′, 1H), 6.77 (s, H5,1H). 13C{1H} NMR (101 MHz, CDCl3) δ 206.95 (C2′), 192.18 (C3),149.43 (C3′), 136.45 (C4′ and C4), 122.80 (C5′), 120.03 (C6′), 103.32(C5).
Reference: [1] Patent: WO2004/72033, 2004, A2, . Location in patent: Page 35
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 16, p. 6389 - 6409
[3] Chemische Berichte, 1992, vol. 125, # 3, p. 701 - 710
[4] RSC Advances, 2015, vol. 5, # 43, p. 34424 - 34431
[5] Inorganic Chemistry, 2015, vol. 54, # 22, p. 10648 - 10655
[6] European Journal of Inorganic Chemistry, 2017, vol. 2017, # 3, p. 651 - 658
[7] Inorganic Chemistry, 2017, vol. 56, # 12, p. 6768 - 6771
[8] Inorganica Chimica Acta, 2019, vol. 484, p. 1 - 7
  • 4
  • [ 66521-54-8 ]
  • [ 75415-03-1 ]
Reference: [1] Synthesis, 2001, # 1, p. 55 - 62
[2] Tetrahedron Letters, 1999, vol. 40, # 26, p. 4779 - 4782
  • 5
  • [ 66521-54-8 ]
  • [ 75415-03-1 ]
Reference: [1] Patent: US5859215, 1999, A,
  • 6
  • [ 66521-54-8 ]
  • [ 7803-57-8 ]
  • [ 75415-03-1 ]
Reference: [1] Dalton Transactions, 2014, vol. 43, # 4, p. 1524 - 1533
  • 7
  • [ 66521-54-8 ]
  • [ 60325-13-5 ]
  • [ 75415-03-1 ]
  • [ 138785-70-3 ]
Reference: [1] Chemische Berichte, 1992, vol. 125, # 3, p. 701 - 710
  • 8
  • [ 66521-54-8 ]
  • [ 60-34-4 ]
  • [ 938066-21-8 ]
  • [ 162435-06-5 ]
Reference: [1] European Journal of Medicinal Chemistry, 2010, vol. 45, # 5, p. 2024 - 2033
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