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[ CAS No. 26661-13-2 ] {[proInfo.proName]}

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Chemical Structure| 26661-13-2
Chemical Structure| 26661-13-2
Structure of 26661-13-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 26661-13-2 ]

CAS No. :26661-13-2 MDL No. :MFCD00239434
Formula : C11H9N3O2 Boiling Point : -
Linear Structure Formula :- InChI Key :XBDUZBHKKUFFRH-UHFFFAOYSA-N
M.W : 215.21 Pubchem ID :309343
Synonyms :
N4-Benzoylcytosine

Calculated chemistry of [ 26661-13-2 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 59.07
TPSA : 74.85 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.66
Log Po/w (XLOGP3) : 0.54
Log Po/w (WLOGP) : 0.83
Log Po/w (MLOGP) : 1.05
Log Po/w (SILICOS-IT) : 1.66
Consensus Log Po/w : 0.95

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.87
Solubility : 2.89 mg/ml ; 0.0134 mol/l
Class : Very soluble
Log S (Ali) : -1.68
Solubility : 4.46 mg/ml ; 0.0207 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -4.08
Solubility : 0.0177 mg/ml ; 0.0000824 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.66

Safety of [ 26661-13-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 26661-13-2 ]

* 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 [ 26661-13-2 ]
  • Downstream synthetic route of [ 26661-13-2 ]

[ 26661-13-2 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 71-30-7 ]
  • [ 98-88-4 ]
  • [ 26661-13-2 ]
YieldReaction ConditionsOperation in experiment
40 kg With dmap; triethylamine In acetonitrile at 5 - 45℃; for 3 h; Inert atmosphere; Large scale Reactor after the replacement of nitrogen, adding 100L acetonitrile, 22 kg (196mol) no water cytosine, 25gDMAP, 24 kg triethylamine, in 5-8 °C lower, slowly dropping 34 kg benzoyl chloride, after dripping, natural to room temperature, in the 25 °C stirring for one hour, then slowly heated to 40-45 °C insulation two hours, then cooling down to room temperature, filter press, the filtrate collected after acetonitrile 60L recycling, the filter cake with water and ethanol washing, drying to obtain the kind of white solid 40 kg, liquid phase content is 99.2percent.
Reference: [1] Patent: US2011/245458, 2011, A1,
[2] Chemical Communications, 2017, vol. 53, # 64, p. 8952 - 8955
[3] Heterocyclic Communications, 2007, vol. 13, # 4, p. 251 - 256
[4] Russian Journal of Organic Chemistry, 2008, vol. 44, # 3, p. 358 - 361
[5] Journal of the Chemical Society, 1956, p. 2388,2392[6] Journal of the Chemical Society, 1958, p. 3028,3032
[7] Chemistry of Natural Compounds, 1983, vol. 19, # 5, p. 580 - 582[8] Khimiya Prirodnykh Soedinenii, 1983, # 5, p. 617 - 619
[9] Patent: US6075143, 2000, A,
[10] Chemistry - A European Journal, 2011, vol. 17, # 51, p. 14508 - 14517
[11] Patent: CN105541728, 2016, A, . Location in patent: Paragraph 0023; 0024
  • 2
  • [ 71-30-7 ]
  • [ 93-97-0 ]
  • [ 26661-13-2 ]
YieldReaction ConditionsOperation in experiment
41 kg With dmap; triethylamine In acetonitrile at 5 - 50℃; for 3 h; Inert atmosphere; Large scale Reactor after the replacement of nitrogen, adding 200L acetonitrile, 22 kg (196mol) no water cytosine, 50gDMAP, 28 kg triethylamine, in 5-10 °C lower, slowly dropping 96 kg (benzoic anhydride solution: 50 wt percent) acetonitrile solution of benzoic anhydride, after dripping, natural to room temperature, in the 25 °C stirring for one hour, then slowly heated to 45-50 °C thermal insulation 2 hours, then reduced to room temperature, filter press, the filtrate collected after acetonitrile 132L recycling, the filter cake is washed with water and ethanol, dried to obtain a white solid 41 kg, liquid phase content of 99.14percent.
Reference: [1] Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 8, p. 2190 - 2210
[2] Patent: CN105541728, 2016, A, . Location in patent: Paragraph 0027; 0028
  • 3
  • [ 6020-40-2 ]
  • [ 98-88-4 ]
  • [ 26661-13-2 ]
YieldReaction ConditionsOperation in experiment
75% With hydrogenchloride; sodium hydroxide In pyridine; ethanol; water EXAMPLE 19
N-4-Benzoylcytosine
Cytosine hemihydrate (12.0 g, 100 mmol) was coevaporated with pyridine and resuspended in 250 ml dry pyridine.
Benzoyl chloride (58 ml, 70.3 g, 500 mmol) was added dropwise (exothermic).
The solution was stirred at RT overnight, and water (50 ml) carefully added.
The solvent was evaporated, and the residue dissolved in 700 ml H2 O containing 55 g NaOH.
The solution was stirred for 1 h after complete dissolution of the material.
Concentrated HCl was then added to pH 4.0, the white precipitate was collected and boiled in 1 liter EtOH, cooled to RT and filtered to give 16.1 g product (75percent).
75% With hydrogenchloride; sodium hydroxide In ethanol; water EXAMPLE 12
N-4-Benzoylcytosine
Cytosine hemihydrate (12.0 g, 100 mmol) was coevaporated with pyridine and resuspended in 250 ml dry pyridines.
Benzoyl chloride (58 ml, 70.3 g, 500 mmol) was added dropwise (exothermic).
The solution was stirred at RT overnight, and water (50 ml) carefully added.
The solvent was evaporated, and the residue dissolved in 700 ml H2O containing 55 g NaOH.
The solution was stirred for 1 h after complete dissolution of the material.
Concentrated HCl was then added to pH 4.0, the white precipitate was collected and boiled in 1 liter EtOH, cooled to RT and filtered to give 16.1 g product (75percent).
75% With hydrogenchloride; sodium hydroxide In pyridine; ethanol; water EXAMPLE 12
N-4-Benzoylcytosine
Cytosine hemihydrate (12.0 g, 100 mmol) was coevaporated with pyridine and resuspended in 250 ml dry pyridine.
Benzoyl chloride (58 ml, 70.3 g, 500 mmol) was added dropwise (exothermic).
The solution was stirred at RT overnight, and water (50 ml) carefully added.
The solvent was evaporated, and the residue dissolved in 700 ml H2O containing 55 g NaOH.
The solution was stirred for 1 h after complete dissolution of the material.
Concentrated HCl was then added to pH 4.0, the white precipitate was collected and boiled in 1 liter EtOH, cooled to RT and filtered to give 16.1 g product (75percent).
Reference: [1] Patent: US5714606, 1998, A,
[2] Patent: US6184389, 2001, B2,
[3] Patent: US6828427, 2004, B1,
  • 4
  • [ 123413-57-0 ]
  • [ 26661-13-2 ]
  • [ 71-30-7 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 9, p. 2547 - 2549
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