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[ CAS No. 793-19-1 ] {[proInfo.proName]}

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Chemical Structure| 793-19-1
Chemical Structure| 793-19-1
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Product Details of [ 793-19-1 ]

CAS No. :793-19-1 MDL No. :MFCD00025891
Formula : C15H21NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :KPRYGTMLHJYBFC-UHFFFAOYSA-N
M.W : 279.33 Pubchem ID :69926
Synonyms :

Calculated chemistry of [ 793-19-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.47
Num. rotatable bonds : 10
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 75.33
TPSA : 55.84 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) : -7.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.23
Log Po/w (XLOGP3) : 1.41
Log Po/w (WLOGP) : 1.46
Log Po/w (MLOGP) : 1.82
Log Po/w (SILICOS-IT) : 2.23
Consensus Log Po/w : 2.03

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.02
Solubility : 2.65 mg/ml ; 0.0095 mol/l
Class : Soluble
Log S (Ali) : -2.19
Solubility : 1.82 mg/ml ; 0.0065 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.91
Solubility : 0.0345 mg/ml ; 0.000124 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.62

Safety of [ 793-19-1 ]

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

Application In Synthesis of [ 793-19-1 ]

* 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 [ 793-19-1 ]
  • Downstream synthetic route of [ 793-19-1 ]

[ 793-19-1 ] Synthesis Path-Upstream   1~16

  • 1
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Reference: [1] Russian Journal of Organic Chemistry, 2003, vol. 39, # 1, p. 49 - 56
[2] Synthetic Communications, 2007, vol. 37, # 18, p. 3143 - 3149
[3] Journal of Labelled Compounds and Radiopharmaceuticals, 2013, vol. 56, # 14, p. 722 - 725
[4] Zhurnal Obshchei Khimii, 1957, vol. 27, p. 3162,3165,3166;engl.Ausg.S.3200,3202,3203
[5] Journal of Heterocyclic Chemistry, 2013, vol. 50, # 6, p. 1374 - 1380
[6] Patent: CN106187863, 2016, A, . Location in patent: Paragraph 0138; 0139; 0140
  • 2
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Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 8, p. 2161 - 2165
  • 3
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  • [ 14002-33-6 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 24, p. 8367 - 8371
  • 4
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Reference: [1] Synlett, 2006, # 14, p. 2246 - 2250
[2] Advanced Synthesis and Catalysis, 2005, vol. 347, # 6, p. 763 - 766
[3] Tetrahedron Letters, 2009, vol. 50, # 14, p. 1653 - 1657
[4] Chemistry Letters, 2003, vol. 32, # 11, p. 988 - 989
[5] New Journal of Chemistry, 2004, vol. 28, # 2, p. 183 - 184
[6] Synlett, 2006, # 10, p. 1549 - 1553
[7] Synlett, 1998, # 9, p. 975 - 976
[8] Molecules, 2008, vol. 13, # 2, p. 340 - 347
[9] Molecules, 2008, vol. 13, # 2, p. 340 - 347
[10] Green Chemistry, 2013, vol. 15, # 6, p. 1550 - 1557
[11] Journal of Molecular Catalysis B: Enzymatic, 2015, vol. 112, p. 76 - 82
[12] Journal of Molecular Catalysis B: Enzymatic, 2015, vol. 112, p. 76 - 82
  • 5
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  • [ 793-19-1 ]
YieldReaction ConditionsOperation in experiment
100% at 20℃; for 8 h; Reflux A solution of benzylamine (10.7 g, 0.1 mol) in MeOH (50 mL) was added in dropwise to a solution of methyl acrylate (18.9 g, .022 mol) in MeOH (100 mL) at rt. The result mixture was refluxed for 8h, and evaporated in vacuum to give 27.9 g product in quantitative yield. ‘H-NIVIR (400 MHz, CDC13) : 7.28 (m., 5H), 3.64 (s, 2H), 3.59 (s, 6H), 2.80 (m, 4H), 2.47 (m, 4H).
99% at 34℃; for 72 h; Inert atmosphere The preparation of dendrimer 6 was carried out using a methodreported in the literature [19] and modified according to ourneeds. In particular, product 3 ( Fig. 1) was prepared startingfrom a solution of benzylamine 1 (0.88mL; 8 mmol) in methanol(20mL) to whichmethylacrylate 2 (2.6 mL; 28.8 mmol) was addedin a dropwise fashion. The resulting reaction mixture was stirredunder argon for 72 h at 34°C. After this time, the solvent was removedunder reduced pressure and the residue obtained confirmedto be pure 3 via 1H NMR and was used in the following stepwithout further purification
99% at 20℃; for 24.5 h; Inert atmosphere Example 7a
Synthesis of N, N-di methyl propionate benzyl amine
To stirred methyl acrylate (112 g, 1302 mmol) and methanol (400 mL) under nitrogen atmosphere, benzyl amine (35 g, 326 mmol) was added drop wise at room temperature over a period of 30 minutes and continued stirring for 24 hours.
The excess of methyl acrylate was removed under reduced pressure using a rotary evaporator to give N, N-di methyl propionate benzyl amine (90 g, 99percent) as pale yellow viscous oil.
IR (cm-1): 1734, 2830, 2952
1H NMR (CDCl3): δ 2.36 (t, 4H, J=5.1 Hz), 2.69 (t, 4H, J=5.4 Hz), 3.4 (s, 2H), 3.53 (s, 6H), 7.1-7.17 (5H, Ar)
98% for 8.5 h; Reflux At room temperature, to a 500mL three-necked bottle, 18.9g (0.22ml) of methyl acrylate and 100mL of methanol were added, and a mixture solution of 10.7g (0.1mol) of benzylamine and 50mL of methanol was slowly added dropwise to the three-necked bottle under stirring. The temperature was naturally elevated, and the addition rate was controlled so that the temperature of reaction system was not greater than 50°C. After the addition, the reaction was stirred at room temperature for 0.5h, and reacted for 8 h under reflux. After completion of the reaction, the unreacted methanol and methyl acrylate were removed by vacuum distillation to obtain light yellow oily product N,N-bis(β-methoxy carbonylethyl) benzylamine, 27.3g, yield 98percent, bp 174-176°C/533Pa.
98% at 20℃; for 8.5 h; Reflux At room temperature, to a 500 mL three-necked bottle, 18.9 g (0.22 mol) of methyl acrylate and 100 mL of methanol were added, and a mixture solution of 10.7 g (0.1 mol) of benzylamine and 50 mL of methanol was slowly added dropwise to the three-necked bottle under stirring.
The temperature was naturally elevated, and the addition rate was controlled so that the temperature of reaction system was not greater than 50° C.
After the addition, the reaction was stirred at room temperature for 0.5 h, and reacted for 8 h under reflux.
After completion of the reaction, the unreacted methanol and methyl acrylate were removed by vacuum distillation to obtain light yellow oily product N,N-bis(β-methoxy carbonylethyl)benzylamine, 27.3 g, yield 98percent, by 174-176° C./533 Pa.
97% for 7 h; To a 250 ml three-necked reaction flask equipped with a mechanical stirrer, a condenser, and a thermometer, 43 g (0.5 mol) of methyl acrylate and 32 g (40 ml) of methyl acrylate were added and 21.4 g (0.2 mol) of benzylamine was added under stirring. The reaction was stirred for 7 hours .After completion of the reaction, excess methyl acrylate and methanol were recovered, and the water pump was distilled under reduced pressure to an inner temperature of 100 to 110 ° C to obtain 54 g of crude product (C) as a yellow oily substance in a yield of 97percent and an amount of 94.3percent.
95% at 20℃; for 20 h; [Example 1: Synthesis of a linker compound] A linker compound of the present invention was synthesized according to the following procedure. As shown in following general formula (10), benzylamine (Compound 1, Bn represents a benzyl group in the formula) was brought into reaction with methyl acrylate (6 equiv.) in methanol (in the formula, MeOH) at room temperature. Two units of methyl acrylate were added by Michael addition to the benzylamine to obtain Compound 2 at the yield of 93percent. Thereafter, a large excess (50 equiv.) of ethylenediamine was added into methanol containing Compound 2 at room temperature. The ethylenediamine was condensed with Compound 2 to obtain Compound 3. It is to be noted that a large excess (50 equiv.) of ethylenediamine is added in order to prevent Compound 2 from condensing simultaneously with two amino groups of ethylenediamine. [] Compound 2 was obtained by the following procedure. A methanol solution (143 mL) of benzylamine (4.7 mL, 44.6 mmol) was mixed with methyl acrylate (8.52 mL, 104 mmol), stirred for 8 hours under nitrogen atmosphere at room temperature, further mixed with methyl acrylate (3.87 mL, 47 mmol), and stirred at room temperature for 12 hours. Thereafter, the stirred solution was further mixed with methyl acrylate (7047 mL, 94 mmol) and stirred overnight to obtain a reaction solution of methanol and methyl acrylate. The methanol/methyl acrylate reaction solution was concentrated under reduced pressure to obtain a residue. The residue was purified by medium-pressure silica gel chromatography (300 g, toluene:ethyl acetate=5:1 to 3:1) to obtain a colorless oily solution serving as Compound 2. Compound 2 was obtained at the yield of 11.7 g (95percent). Also, 1H NMR (400 MHz, CD3OD) measurement was conducted on Compound 2 so obtained to find that δ7.28-7.20 (5H, m, aromatic), δ4.79 (6H, s, OMe*.x.2), δ3.57 (2H, d, J=4.6 Hz, NCH2*Ph), δ2.76 (4H, td, Jgem=4.6, Jvic=6.8 Hz , CH2*NBn), δ2.46 (4H, td, Jgem=4.6, Jvic=6.8 Hz, COCH2*CH2NBn). It is to be noted that each chemical shift δ indicates a measured value corresponding to a proton having a plurality of Hs marked with *, i.e., H*. The same applies to the following description. An ESI-MS (positive) measurement (time-of-flight mass spectrometer measurement) was conducted to find that the m/z (mass/charge) was 302.1 [(M+Na)+].

Reference: [1] Patent: WO2017/15106, 2017, A1, . Location in patent: Page/Page column 30
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 2013, vol. 56, # 14, p. 722 - 725
[3] Planta Medica, 2017, vol. 83, # 5, p. 420 - 425
[4] Patent: US2017/274362, 2017, A1, . Location in patent: Paragraph 0077-0079
[5] Patent: EP2570410, 2013, A1, . Location in patent: Paragraph 0062
[6] Patent: US2013/231369, 2013, A1, . Location in patent: Paragraph 0100
[7] Patent: CN106187863, 2016, A, . Location in patent: Paragraph 0135; 0136; 0137
[8] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 8, p. 2161 - 2165
[9] Patent: EP1548016, 2005, A1, . Location in patent: Page/Page column 15
[10] Synthetic Communications, 2007, vol. 37, # 18, p. 3143 - 3149
[11] Russian Journal of Organic Chemistry, 2003, vol. 39, # 1, p. 49 - 56
[12] Synthetic Communications, 2006, vol. 36, # 6, p. 795 - 801
[13] RSC Advances, 2018, vol. 8, # 9, p. 4531 - 4547
[14] Journal of the American Chemical Society, 1950, vol. 72, p. 3298
[15] Journal of pharmaceutical sciences, 1972, vol. 61, # 11, p. 1739 - 1745
[16] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 7, p. 1885 - 1892
[17] Journal of Organic Chemistry, 2000, vol. 65, # 24, p. 8367 - 8371
[18] Journal of Heterocyclic Chemistry, 2013, vol. 50, # 6, p. 1374 - 1380
[19] Molecules, 2018, vol. 23, # 9,
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  • [ 23574-01-8 ]
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Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2015, vol. 112, p. 76 - 82
  • 7
  • [ 3395-91-3 ]
  • [ 37488-40-7 ]
  • [ 23574-01-8 ]
  • [ 793-19-1 ]
Reference: [1] RSC Advances, 2014, vol. 4, # 35, p. 18229 - 18233
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Reference: [1] Green Chemistry, 2013, vol. 15, # 6, p. 1550 - 1557
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Reference: [1] Green Chemistry, 2013, vol. 15, # 6, p. 1550 - 1557
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Reference: [1] Green Chemistry, 2013, vol. 15, # 6, p. 1550 - 1557
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Reference: [1] Green Chemistry, 2013, vol. 15, # 6, p. 1550 - 1557
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Reference: [1] Patent: CN106187863, 2016, A,
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Reference: [1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 7, p. 1885 - 1892
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Reference: [1] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 7, p. 1885 - 1892
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Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 24, p. 8367 - 8371
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Reference: [1] Molecules, 2018, vol. 23, # 9,
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