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[ CAS No. 17061-63-1 ] {[proInfo.proName]}

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Chemical Structure| 17061-63-1
Chemical Structure| 17061-63-1
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Product Details of [ 17061-63-1 ]

CAS No. :17061-63-1 MDL No. :MFCD14583080
Formula : C9H11NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :DATDKKQVOOSHGC-UHFFFAOYSA-N
M.W : 165.19 Pubchem ID :14906816
Synonyms :

Calculated chemistry of [ 17061-63-1 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.1
TPSA : 38.33 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) : 1.83
Log Po/w (XLOGP3) : 1.11
Log Po/w (WLOGP) : 0.79
Log Po/w (MLOGP) : 1.37
Log Po/w (SILICOS-IT) : 1.53
Consensus Log Po/w : 1.33

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.67
Solubility : 3.54 mg/ml ; 0.0214 mol/l
Class : Very soluble
Log S (Ali) : -1.51
Solubility : 5.13 mg/ml ; 0.031 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.92
Solubility : 0.198 mg/ml ; 0.0012 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 17061-63-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 17061-63-1 ]

* 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 [ 17061-63-1 ]
  • Downstream synthetic route of [ 17061-63-1 ]

[ 17061-63-1 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 77287-34-4 ]
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YieldReaction ConditionsOperation in experiment
87% at 20℃; for 0.5 h; Microwave irradiation; Sealed tube General procedure: General procedure for the 1,4-dioxane mediated transamidation of amides with an amine under microwave. An oven-dried 10-mL microwave reaction vial containing a Teflon-coated magnetic stir bar was charged with carboxamide (1 mmol), amine (1 mmol), and dioxane (2 ml) (undried). The vessel was sealed with a plastic microwave septum, stirred at room temperature for 5 min and then placed into the MW cavity for a specified temperature and time. After the completion of reaction (TLC), the mixture was cooled to room temperature; distilled water (10 mL) was added to it and then extracted with ethyl acetate (3 10 mL). The combined organic phase was dried over anhydrous Na2SO4, filtered and then concentrated using a rotary vacuum evaporator. The crude product was purified by column chromatography using a mixture of ethyl acetate/n-hexane (10–20percent of ethyl acetate depending upon the product) as an eluent
81% With [Ru-NHC] In toluene at 110℃; for 8 h; Inert atmosphere; Schlenk technique; Sealed tube General procedure: A mixture of amide (5mmol), amine (5mmol), [Ru–NHC] complex (0.5molpercent) and toluene (5mL) was stirred in a sealed tube under nitrogen atmosphere at 110°C for 8h. After cooling down to room temperature, the reaction solvent was removed under vacuum. After removal of the solvent, the crude reaction mixture was dissolved in CH2Cl2 and purified by column chromatography on silica gel (200–400mesh) eluting with heptane:ethanol [25:1] to give corresponding amides as a white solid. The yields are mentioned in Tables 3–5. The product was confirmed by NMR spectroscopy. Reported isolated yields are an average of two runs.
Reference: [1] Chemical Communications (Cambridge, United Kingdom), 2012, vol. 48, # 95, p. 11626 - 11628,3
[2] Chemical Communications, 2012, vol. 48, # 95, p. 11626 - 11628
[3] Tetrahedron Letters, 2013, vol. 54, # 20, p. 2553 - 2555
[4] RSC Advances, 2016, vol. 6, # 58, p. 52724 - 52728
[5] Journal of Molecular Catalysis A: Chemical, 2015, vol. 403, p. 15 - 26
  • 2
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Reference: [1] Chemical Communications (Cambridge, United Kingdom), 2012, vol. 48, # 92, p. 11310 - 11312,3
[2] Green Chemistry, 2017, vol. 19, # 1, p. 88 - 92
[3] Patent: CN105272868, 2016, A, . Location in patent: Paragraph 0034; 0035
[4] Patent: CN106278923, 2017, A, . Location in patent: Paragraph 0027; 0028
  • 3
  • [ 64-18-6 ]
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Reference: [1] Synlett, 2004, # 14, p. 2570 - 2572
[2] Angewandte Chemie - International Edition, 2013, vol. 52, # 48, p. 12714 - 12718[3] Angew. Chem., 2013, vol. 125, # 48, p. 12946 - 12950,5
[4] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 9, p. 2437 - 2451
  • 4
  • [ 67-56-1 ]
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Reference: [1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 4, p. 834 - 840
[2] Organic Letters, 2013, vol. 15, # 7, p. 1776 - 1779
[3] Chemistry - A European Journal, 2013, vol. 19, # 36, p. 11832 - 11836
[4] Angewandte Chemie - International Edition, 2017, vol. 56, # 15, p. 4229 - 4233[5] Angew. Chem., 2017, vol. 129, # 15, p. 4293 - 4297,5
[6] Patent: WO2017/137984, 2017, A1, . Location in patent: Paragraph 00406; 00407
  • 5
  • [ 124-38-9 ]
  • [ 2393-23-9 ]
  • [ 17061-63-1 ]
Reference: [1] Chemical Communications, 2018, vol. 54, # 81, p. 11395 - 11398
[2] ACS Catalysis, 2017, vol. 7, # 4, p. 2500 - 2504
[3] Angewandte Chemie - International Edition, 2015, vol. 54, # 41, p. 12116 - 12120[4] Angew. Chem., 2015, vol. 127, p. 12284 - 12288,5
  • 6
  • [ 50-00-0 ]
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  • [ 17061-63-1 ]
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 26, p. 7564 - 7567[2] Angew. Chem., 2015, vol. 127, p. 7674 - 7677
[3] Green Chemistry, 2016, vol. 18, # 3, p. 808 - 816
[4] Tetrahedron Letters, 2010, vol. 51, # 44, p. 5804 - 5806
  • 7
  • [ 2393-23-9 ]
  • [ 109-94-4 ]
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YieldReaction ConditionsOperation in experiment
88% at 150℃; for 12 h; To a stirred solution of 4-methoxybenzylamine (3.93 mL, 30 mmol) was added ethyl formate (2.45 mL, 24.2 mmol). The reaction mixture was stirred and heated at 150 °C for 12 h. The reaction mixture was cooled to room temperature and the precipitate was collected by filtration, dried and washed with ethyl ether to give 5b as a white solid (4.4 g). Yield: 88percent; mp 79-80 °C; IR (KBr) cm-1: 3286 (s, N-H); 3012 (m, C-H); 2943-2834 (m, C-H); 1645 (s, CO). 1H NMR (400 MHz, DMSO-d6) δ: 3.73 (s, 3H, OCH3); 4.22 (d, 2H, CH2-NH); 6.89 (d, 2H, H3 + H5, J3-2 = J5-6 = 8.5 Hz); 7.19 (d, 2H, H2 + H6); 8.1 (s, 1H, H-CO); 8.43 (s, 1H, CH2-NH); Elemental Analysis for C9H11NO2 Calcd/Found (percent): C: 65.45/65.07; H: 6.66/6.37; N: 8.48/8.29.
Reference: [1] Chemical Communications, 2017, vol. 53, # 15, p. 2382 - 2385
[2] New Journal of Chemistry, 2017, vol. 41, # 12, p. 5075 - 5081
[3] Tetrahedron Letters, 2009, vol. 50, # 37, p. 5210 - 5214
[4] European Journal of Medicinal Chemistry, 2012, vol. 47, # 1, p. 283 - 298
[5] Journal of Medicinal Chemistry, 1983, vol. 26, # 3, p. 309 - 312
[6] Tetrahedron Letters, 1985, vol. 26, # 48, p. 5863 - 5866
[7] Pharmazie, 2015, vol. 70, # 8, p. 507 - 510
[8] Journal of Medicinal Chemistry, 2017, vol. 60, # 16, p. 7199 - 7205
[9] Chemistry - A European Journal, 2017, vol. 23, # 52, p. 12758 - 12762
  • 8
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YieldReaction ConditionsOperation in experiment
40% at 50℃; for 1.5 h; General procedure: Typical procedure for formylation of amines After the hydrosilylation of CO2 with 1a was completed, piperidine (4a, 1 mmol) was added to the reaction solution of dimethylphenylsilyl formate (2a) and the reaction mixture was vigorously stirred at 50 °C for 1 h. The conversion and the yield of the products were determined by GC and 1H NMR analyses. The formamides were confirmed by the comparison of their GC retention times and GC mass spectra. A typical procedure for isolation of formamides is as follows: After the hydrosilylation of CO2 with 1a was completed, acetonitrile was removed by evaporation, followed by addition of n-hexane (2 mL). Catalysts (Rh2(OAc)4 and K2CO3) were insoluble in n-hexane and separated by filtration. Then, 4e (1 mmol) was added to the filtrate, and the mixture was vigorously stirred at 50 °C for 1 h. n-Hexane was evaporated, and white precipitates obtained were washed with n-hexane and extracted with toluene.
Evaporation of toluene afforded analytically pure N-benzylformamide (5e, 35percent yield).
Reference: [1] Journal of Molecular Catalysis A: Chemical, 2013, vol. 366, p. 347 - 352
  • 9
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  • [ 68-12-2 ]
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Reference: [1] RSC Advances, 2016, vol. 6, # 58, p. 52724 - 52728
[2] Journal of Organic Chemistry, 2013, vol. 78, # 9, p. 4512 - 4523
[3] Chemical Communications, 2014, vol. 50, # 19, p. 2438 - 2441
  • 10
  • [ 201230-82-2 ]
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  • [ 93731-94-3 ]
Reference: [1] Chemical Communications, 2009, # 8, p. 947 - 949
  • 11
  • [ 67-56-1 ]
  • [ 874-90-8 ]
  • [ 17061-63-1 ]
Reference: [1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 4, p. 834 - 840
  • 12
  • [ 2393-23-9 ]
  • [ 68-12-2 ]
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  • [ 124-40-3 ]
Reference: [1] Patent: CN104447379, 2017, B, . Location in patent: Paragraph 0041; 0042; 0052
  • 13
  • [ 123-11-5 ]
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Reference: [1] ACS Combinatorial Science, 2015, vol. 17, # 9, p. 493 - 499
  • 14
  • [ 124-38-9 ]
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  • [ 1262617-99-1 ]
Reference: [1] Green Chemistry, 2016, vol. 18, # 14, p. 3956 - 3961
  • 15
  • [ 3717-21-3 ]
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1961, vol. 9, # 12, p. 945 - 948
  • 16
  • [ 77287-34-4 ]
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Reference: [1] Chemische Berichte, 1954, vol. 87, p. 531,534[2] Chemische Berichte, 1956, vol. 89, p. 1532
  • 17
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  • [ 105-13-5 ]
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  • [ 122-91-8 ]
Reference: [1] Chemische Berichte, 1954, vol. 87, p. 531,534[2] Chemische Berichte, 1956, vol. 89, p. 1532
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