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[ CAS No. 94-93-9 ] {[proInfo.proName]}

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Chemical Structure| 94-93-9
Chemical Structure| 94-93-9
Structure of 94-93-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 94-93-9 ]

CAS No. :94-93-9 MDL No. :MFCD00002244
Formula : C16H16N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :VEUMANXWQDHAJV-UHFFFAOYSA-N
M.W : 268.31 Pubchem ID :26518
Synonyms :

Calculated chemistry of [ 94-93-9 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.12
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 81.73
TPSA : 65.18 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 : Yes
Log Kp (skin permeation) : -6.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.41
Log Po/w (XLOGP3) : 2.06
Log Po/w (WLOGP) : 2.64
Log Po/w (MLOGP) : 1.57
Log Po/w (SILICOS-IT) : 3.98
Consensus Log Po/w : 2.53

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.92
Solubility : 0.326 mg/ml ; 0.00122 mol/l
Class : Soluble
Log S (Ali) : -3.06
Solubility : 0.235 mg/ml ; 0.000876 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.76
Solubility : 0.00465 mg/ml ; 0.0000173 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.5

Safety of [ 94-93-9 ]

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 [ 94-93-9 ]

* 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 [ 94-93-9 ]
  • Downstream synthetic route of [ 94-93-9 ]

[ 94-93-9 ] Synthesis Path-Upstream   1~7

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YieldReaction ConditionsOperation in experiment
90% at 20℃; for 1 h; c) Synthesis of VO(salen) catalyst; Step 1 : salen; Salicaldehyde (7.307 g, 6.38 ml, 0. 0598 mol) and ethylene diamine (1. 798 g, 2 ml, 0.0299 mol) were combined in absolute EtOH and stirred for 1 hour at room temperature. The resulting precipitate was filtered, washed with EtOH and air dried. Yield: 7.25 g (90percent).
88% Reflux General procedure: The Schiff bases used for the synthesis of the catalysts were prepared by the well known reaction between salicylaldehyde and diamine. Slight experimental variations were introduced with respect to literature methods [27] and the resulting procedure was successfully applied to a number of differently substituted aldehydes. (0015) General procedure: Two equivalents of the appropriate salicylaldehyde were dissolved in the minimum volume of boiling methanol (generally, 20 ml) and added dropwise with one equivalent of diamine (either 1,2-diaminoethane or 1,2-benzenediamine) in 5 ml methanol. The solution was refluxed until all the aldehyde disappeared (TLC analysis) and then cooled to room temperature, thus causing precipitation of the Schiff base, as a yellow solid. The filtered solid was washed with a small amount of methanol, then with diethyl ether and dried. The following Schiff bases were prepared: (0016) Salophen, [1,2-bis-(salicylideneamino)benzene]: yield 95.3percent; 5,5′-Cl2salophen, [1,2-bis-(5-Cl-salicylideneamino)benzene]: yield >99percent; 5,5′-(t-Bu)2salophen [1,2-bis-(5-t-Bu-salicylideneamino)benzene]: yield 75percent; 3,3′-(OMe)2salophen, [1,2-bis-(3-OMe-salicylideneamino)-benzene]: yield 77percent; 5,5′-(OMe)2salophen, [1,2-bis-(5-OMe-salicylideneamino)-benzene]: yield 79percent; 3,3′,5,5′-Cl4salophen [1,2-bis-(3,5-Cl2salicylideneamino)benzene]: yield 95percent; 3,3′,5,5′-(t-Bu)4salophen [1,2-bis-(3,5-di-t-Bu-salicylideneamino)benzene]: yield 75percent. (0017) Salen, [1,2-bis-(salicylideneamino)ethane]: yield 88percent; 5,5′-Cl2salen, [1,2-bis-(5-Cl-salicylideneamino)ethane]: yield 67percent; 5,5′-(t-Bu)2salen, [1,2-bis-(5-t-Bu-salicylideneamino)ethane]: yield 91percent; 3,3′-(OMe)2salen, [1,2-bis-(3-methoxy-salicylideneamino)ethane]: yield 92percent; 5,5′-(OMe)2salen, [1,2-bis-(5-OMe-salicylideneamino)ethane]: yield 92percent; 3,3′,5,5′-Cl4salen, [1,2-bis-(3,5-Cl2-salicylideneamino)ethane]: yield 70percent; 3,3′,5,5′-(t-Bu)4salen, [1,2-bis-(3,5-(t-Bu)2-salicylideneamino)ethane]: yield 72percent. (0018) All the compounds gave 1H NMR and UV–vis spectra consistent with the structure and with literature data [25,28–30].
79% With polymer supported zinc(II)-salen complex In water at 80℃; for 2 h; Green chemistry General procedure: Varying the procedure from the literature, 10 mg catalyst was added to a solution of ethylenediamine (1 mmol, 60 mg) and 2 mmol of benzaldehyde derivative in 10 mL distilled water and refluxed at 80 °C for 2 h. The reaction mixture was poured onto ice, and the resulting precipitate was dissolved in ethyl acetate and the catalyst was separated by filtration. Evaporate off EtOAc to get Schiff bases, which can be further recrystallized using ethanol. (4a) 2,2’-((1E,1’E)-(Ethane-1,2-diylbis(azanylylidene))bis (methanylylidene))diphenol (Yield = 79percent); 1H NMR (400 MHz, CDCl3) δ = 13.19 (s, 2H), 8.35 (s, 2H), 7.30-7.21 (m, 4H), 6.94 (d, J = 8.35 Hz, 2H), 6.8 (t, J = 7.75 Hz, 2H), 3.93 (S, 4H). 13C NMR (100 MHz, CDCl3) 166.52, 161.02, 132.41, 131.50, 118.69, 118.65, 116.97, 59.77. GC-MS m/z: calcd. for C16H16N2O2: 268.1212 and found 268.2494.
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[2] Green Chemistry, 2014, vol. 16, # 3, p. 1374 - 1382
[3] Patent: WO2005/70911, 2005, A1, . Location in patent: Page/Page column 35-36
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[5] Journal of Materials Chemistry C, 2015, vol. 3, # 42, p. 11099 - 11110
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[9] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1987, p. 3055 - 3060
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[16] Patent: EP2039679, 2009, A1, . Location in patent: Page/Page column 10
[17] Patent: EP2039679, 2009, A1, . Location in patent: Page/Page column 10; 11
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[21] Applied Organometallic Chemistry, 2017, vol. 31, # 10,
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[2] European Journal of Inorganic Chemistry, 2005, # 4, p. 732 - 744
[3] Organic Preparations and Procedures International, 2005, vol. 37, # 2, p. 173 - 177
[4] Journal of the American Chemical Society, 2004, vol. 126, # 48, p. 15660 - 15661
[5] Journal of the Indian Chemical Society, 1998, vol. 75, # 3, p. 160 - 161
[6] Journal of Organic Chemistry, 2004, vol. 69, # 4, p. 1357 - 1359
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YieldReaction ConditionsOperation in experiment
95.9% With ethylenediamine In ethanol Catalytic Disproportionation of Hydrogen Peroxide
EXAMPLE 41
Preparation of: STR78
A solution of salicylaldehyde (24.42 g, 0.200 molc) in 80 ml of EtOh was added to a stirred solution of ethylenediamine (6.070 g, 0.100, olc) in a mixture of 50 ml EtOH and 50 ml of H2 O over a period of 5 minutes.
The reaction mixture was refluxed for 1 hour and stirred at room temperature overnight.
The yellow crystalline product was separated by filtration and washed with 2*30 ml of cold 60percent EtOh and air dried to yield 25.733 g (95.9percent) of salen.
Reference: [1] Patent: US5637739, 1997, A,
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Reference: [1] Heterocycles, 2006, vol. 68, # 3, p. 531 - 537
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Reference: [1] Chemical Communications, 2007, # 39, p. 4006 - 4008
[2] Dalton Transactions, 2008, # 22, p. 2966 - 2973
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Reference: [1] Dalton Transactions, 2008, # 22, p. 2966 - 2973
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Reference: [1] Journal of Organic Chemistry, 1959, vol. 24, p. 1905
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