Home Cart 0 Sign in  

[ CAS No. 14205-39-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 14205-39-1
Chemical Structure| 14205-39-1
Structure of 14205-39-1 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 14205-39-1 ]

Related Doc. of [ 14205-39-1 ]

Alternatived Products of [ 14205-39-1 ]

Product Details of [ 14205-39-1 ]

CAS No. :14205-39-1 MDL No. :MFCD00008072
Formula : C5H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 115.13 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 14205-39-1 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.4
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 29.67
TPSA : 52.32 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) : -6.58 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.58
Log Po/w (XLOGP3) : 0.6
Log Po/w (WLOGP) : 0.02
Log Po/w (MLOGP) : -0.09
Log Po/w (SILICOS-IT) : -0.39
Consensus Log Po/w : 0.35

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.8
Solubility : 18.3 mg/ml ; 0.159 mol/l
Class : Very soluble
Log S (Ali) : -1.27
Solubility : 6.15 mg/ml ; 0.0534 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.02
Solubility : 110.0 mg/ml ; 0.957 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.0

Safety of [ 14205-39-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 14205-39-1 ]

* 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 [ 14205-39-1 ]
  • Downstream synthetic route of [ 14205-39-1 ]

[ 14205-39-1 ] Synthesis Path-Upstream   1~37

  • 1
  • [ 609-02-9 ]
  • [ 14205-39-1 ]
  • [ 4664-13-5 ]
Reference: [1] ACS Medicinal Chemistry Letters, 2014, vol. 5, # 6, p. 711 - 716
  • 2
  • [ 99-61-6 ]
  • [ 14205-39-1 ]
  • [ 21881-77-6 ]
YieldReaction ConditionsOperation in experiment
77% With graphite oxide In neat (no solvent) at 80℃; for 2 h; General procedure: A mixture of aldehyde 1a–1j (1 mmol), methyl 3-aminocrotonate(5 mmol), and amount of GO (as indicated inTable 2) was stirred in reflux of solvent under ambient airfor indicated time in Table 2. After completion of thereaction, the residue was dissolved in CH2Cl2 and filteredthrough a sintered funnel. The filtrate was evaporated andpurified by recrystallization from EtOH
Reference: [1] Monatshefte fur Chemie, 2014, vol. 145, # 12, p. 1919 - 1924
[2] Medicinal Chemistry Research, 2011, vol. 20, # 8, p. 1325 - 1330
  • 3
  • [ 99-61-6 ]
  • [ 105-45-3 ]
  • [ 14205-39-1 ]
  • [ 21881-77-6 ]
Reference: [1] Organic Process Research and Development, 2001, vol. 5, # 4, p. 452 - 455
[2] Synthetic Communications, 1995, vol. 25, # 6, p. 857 - 862
[3] Biochemical Pharmacology, 2003, vol. 65, # 3, p. 329 - 338
  • 4
  • [ 99-61-6 ]
  • [ 14205-39-1 ]
  • [ 21881-77-6 ]
  • [ 76258-20-3 ]
YieldReaction ConditionsOperation in experiment
74% With graphite oxide In water for 7 h; Reflux General procedure: A mixture of aldehyde 1a–1j (1 mmol), methyl 3-aminocrotonate(5 mmol), and amount of GO (as indicated inTable 2) was stirred in reflux of solvent under ambient airfor indicated time in Table 2. After completion of thereaction, the residue was dissolved in CH2Cl2 and filteredthrough a sintered funnel. The filtrate was evaporated andpurified by recrystallization from EtOH
55% With graphite oxide In water for 7 h; Reflux General procedure: A mixture of aldehyde 1a–1j (1 mmol), methyl 3-aminocrotonate(5 mmol), and amount of GO (as indicated inTable 2) was stirred in reflux of solvent under ambient airfor indicated time in Table 2. After completion of thereaction, the residue was dissolved in CH2Cl2 and filteredthrough a sintered funnel. The filtrate was evaporated andpurified by recrystallization from EtOH
Reference: [1] Monatshefte fur Chemie, 2014, vol. 145, # 12, p. 1919 - 1924
[2] Monatshefte fur Chemie, 2014, vol. 145, # 12, p. 1919 - 1924
  • 5
  • [ 41097-40-9 ]
  • [ 14205-39-1 ]
  • [ 21881-77-6 ]
Reference: [1] ACH - Models in Chemistry, 1994, vol. 131, # 3-4, p. 383 - 396
  • 6
  • [ 39562-17-9 ]
  • [ 14205-39-1 ]
  • [ 21881-77-6 ]
Reference: [1] Arzneimittel-Forschung/Drug Research, 1981, vol. 31, # 3, p. 407 - 409
  • 7
  • [ 141-97-9 ]
  • [ 99-61-6 ]
  • [ 14205-39-1 ]
  • [ 21881-77-6 ]
  • [ 21829-28-7 ]
  • [ 39562-70-4 ]
Reference: [1] Archiv der Pharmazie, 1989, vol. 322, # 5, p. 253 - 256
  • 8
  • [ 61312-59-2 ]
  • [ 14205-39-1 ]
  • [ 63675-72-9 ]
Reference: [1] Applied Catalysis A: General, 2017, vol. 530, p. 203 - 210
  • 9
  • [ 107-02-8 ]
  • [ 14205-39-1 ]
  • [ 65719-09-7 ]
Reference: [1] Chemical Communications, 2017, vol. 53, # 15, p. 2390 - 2393
[2] Journal of Heterocyclic Chemistry, 1991, vol. 28, # 5, p. 1315 - 1324
  • 10
  • [ 126192-87-8 ]
  • [ 14205-39-1 ]
  • [ 21829-25-4 ]
Reference: [1] Patent: US5126457, 1992, A,
  • 11
  • [ 105-45-3 ]
  • [ 14205-39-1 ]
  • [ 21829-25-4 ]
Reference: [1] Patent: US5126457, 1992, A,
  • 12
  • [ 105-45-3 ]
  • [ 552-89-6 ]
  • [ 14205-39-1 ]
  • [ 21829-25-4 ]
Reference: [1] Indian Journal of Chemistry - Section B Organic Chemistry Including Medicinal Chemistry, 1990, vol. 29, # 3, p. 277 - 279
[2] Organic Process Research and Development, 2001, vol. 5, # 4, p. 452 - 455
  • 13
  • [ 14205-39-1 ]
  • [ 105-45-3 ]
  • [ 552-89-6 ]
  • [ 21829-25-4 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 44, p. 8083 - 8086
  • 14
  • [ 126192-87-8 ]
  • [ 105-45-3 ]
  • [ 14205-39-1 ]
  • [ 21829-25-4 ]
Reference: [1] Synthetic Communications, 1992, vol. 22, # 1, p. 47 - 61
  • 15
  • [ 126192-88-9 ]
  • [ 105-45-3 ]
  • [ 14205-39-1 ]
  • [ 21829-25-4 ]
Reference: [1] Synthetic Communications, 1992, vol. 22, # 1, p. 47 - 61
  • 16
  • [ 139445-58-2 ]
  • [ 105-45-3 ]
  • [ 14205-39-1 ]
  • [ 21829-25-4 ]
Reference: [1] Synthetic Communications, 1992, vol. 22, # 1, p. 47 - 61
  • 17
  • [ 14205-39-1 ]
  • [ 21829-25-4 ]
Reference: [1] Tetrahedron, 1998, vol. 54, # 14, p. 3589 - 3606
  • 18
  • [ 555-16-8 ]
  • [ 105-45-3 ]
  • [ 14205-39-1 ]
  • [ 21829-09-4 ]
Reference: [1] Organic Process Research and Development, 2001, vol. 5, # 4, p. 452 - 455
[2] Synthetic Communications, 1995, vol. 25, # 6, p. 857 - 862
  • 19
  • [ 14205-39-1 ]
  • [ 36745-93-4 ]
Reference: [1] Patent: US2014/148454, 2014, A1,
[2] Patent: WO2014/82739, 2014, A1,
[3] Patent: WO2015/131080, 2015, A1,
[4] Patent: WO2005/110416, 2005, A2,
  • 20
  • [ 105-45-3 ]
  • [ 14205-39-1 ]
YieldReaction ConditionsOperation in experiment
85% With ammonia In methanol at 0 - 10℃; for 4 h; Large scale 25kg of methyl acetoacetate and 20kg of methanol were pumped into the ammoniation reaction tank.The internal temperature was controlled to 0 to 10 ° C with iced water, stirred, and ammonia gas was introduced, and white crystals were precipitated, and the ammonia was stopped after 4 hours.After freezing overnight, the mixture was centrifuged to obtain white crystals, which was placed in an ammoniated refining tank, and 15 kg of methanol for purification was added thereto, and the mixture was heated to dissolve, and then freeze-crystallized at 0 to -10 ° C for 20 to 24 hours.The mixture was centrifuged and filtered, and the filter cake was dried in a hot air circulating oven at 50 to 60 ° C for 8 hours to obtain methyl 3-aminocrotonate of 18.6 to 21 kg, and the weight yield range was 74.4 to 84.0percent, and the molar yield range was 75.0 to 85.0percent.
Reference: [1] Chemical and Pharmaceutical Bulletin, 1989, vol. 37, # 8, p. 2117 - 2121
[2] Patent: WO2012/147103, 2012, A2, . Location in patent: Page/Page column 6-7
[3] Patent: CN108164454, 2018, A, . Location in patent: Paragraph 0024; 0026; 0027
[4] Journal of the Chemical Society of Pakistan, 2011, vol. 33, # 6, p. 916 - 921
[5] Journal of the American Chemical Society, 2010, vol. 132, # 28, p. 9585 - 9587
[6] New Journal of Chemistry, 2005, vol. 29, # 12, p. 1567 - 1576
[7] Tetrahedron Letters, 2011, vol. 52, # 34, p. 4412 - 4416
[8] Chemische Berichte, 1887, vol. 20, p. 3054
[9] Chemische Berichte, 1922, vol. 55, p. 2075
[10] Chemische Berichte, 1887, vol. 20, p. 3054
[11] Chemical and Pharmaceutical Bulletin, 1979, vol. 27, # 6, p. 1426 - 1440
[12] Arzneimittel-Forschung/Drug Research, 1981, vol. 31, # 3, p. 407 - 409
[13] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1994, vol. 33, # 5, p. 451 - 454
[14] Journal of Organic Chemistry, 1999, vol. 64, # 18, p. 6907 - 6910
[15] Organic Letters, 2004, vol. 6, # 6, p. 1013 - 1016
[16] Journal of the American Chemical Society, 2002, vol. 124, # 49, p. 14552 - 14553
[17] European Journal of Organic Chemistry, 2008, # 19, p. 3352 - 3362
[18] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 4, p. 1579 - 1586
[19] Organic Letters, 2011, vol. 13, # 7, p. 1754 - 1757
[20] Organic Letters, 2012, vol. 14, # 21, p. 5480 - 5483,4
[21] Organic Letters, 2012, vol. 14, # 21, p. 5480 - 5483
[22] Organic Process Research and Development, 2007, vol. 11, # 3, p. 568 - 577
[23] RSC Advances, 2014, vol. 4, # 37, p. 19111 - 19121
[24] Archives of Pharmacal Research, 2013, vol. 36, # 11, p. 1392 - 1402
[25] Organic Letters, 2014, vol. 16, # 20, p. 5410 - 5413
[26] Journal of the American Chemical Society, 2014, vol. 136, # 46, p. 16120 - 16123
[27] European Journal of Pharmacology, 2015, vol. 746, p. 233 - 244
[28] Tetrahedron, 2015, vol. 71, # 36, p. 6196 - 6203
[29] Advanced Synthesis and Catalysis, 2016, vol. 358, # 13, p. 2035 - 2040
[30] Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 1452 - 1458
  • 21
  • [ 57570-85-1 ]
  • [ 14205-39-1 ]
Reference: [1] Chemistry - An Asian Journal, 2012, vol. 7, # 10, p. 2196 - 2198,3
[2] Chemistry - An Asian Journal, 2012, vol. 7, # 10, p. 2196 - 2198
  • 22
  • [ 7664-41-7 ]
  • [ 105-45-3 ]
  • [ 14205-39-1 ]
Reference: [1] Organic Letters, 2012, vol. 14, # 13, p. 3506 - 3509
  • 23
  • [ 6372-01-6 ]
  • [ 14205-39-1 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1895, vol. <3> 13, p. 71
  • 24
  • [ 105-45-3 ]
  • [ 5977-14-0 ]
  • [ 14205-39-1 ]
Reference: [1] Monatshefte fuer Chemie, 1907, vol. 28, p. 4
[2] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1905, vol. <5> 14 I, p. 395[3] Chem. Zentralbl., 1905, vol. 76, # I, p. 1559
[4] Chemische Berichte, 1905, vol. 38, p. 1127[5] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1905, vol. <5> 14 I, p. 394[6] Chem. Zentralbl., 1905, vol. 76, # I, p. 1559
  • 25
  • [ 105-45-3 ]
  • [ 5977-14-0 ]
  • [ 14205-39-1 ]
Reference: [1] Monatshefte fuer Chemie, 1907, vol. 28, p. 4
[2] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1905, vol. <5> 14 I, p. 395[3] Chem. Zentralbl., 1905, vol. 76, # I, p. 1559
[4] Chemische Berichte, 1905, vol. 38, p. 1127[5] Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1905, vol. <5> 14 I, p. 394[6] Chem. Zentralbl., 1905, vol. 76, # I, p. 1559
  • 26
  • [ 104-88-1 ]
  • [ 14205-39-1 ]
  • [ 105-45-3 ]
  • [ 73257-49-5 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 44, p. 8083 - 8086
  • 27
  • [ 104-88-1 ]
  • [ 105-45-3 ]
  • [ 14205-39-1 ]
  • [ 73257-49-5 ]
Reference: [1] Organic Process Research and Development, 2001, vol. 5, # 4, p. 452 - 455
  • 28
  • [ 541-50-4 ]
  • [ 99-61-6 ]
  • [ 14205-39-1 ]
  • [ 74936-72-4 ]
YieldReaction ConditionsOperation in experiment
83% With polyphosphoric acid In ethanolReflux; Inert atmosphere General procedure: A solution of ethyl acetoacetate (3) (576 mg, 4.4 mmol),4-fluoro benzaldehyde (1a) (500 mg, 4 mmol) and thiourea(2) (306 mg, 4 mmol) in ethanol (5 mL) was heated under reflux (78-80 °C) in the presence of poly phosphoric acid(1350 mg, 4 mmol) for 12 h under nitrogen. The progress ofthe reaction was monitored by TLC (hexane: ethyl acetate,1:1 v/v). The reaction mixture, after being concentrated under vacuum at 60 °C, cooled to room temperature, it was poured into crushed ice (10 g) and stirred for 5-10 min. The solid separated was then filtered under suction, washed withice-cold water (20 mL) and then recrystallized from hot ethanol to afford pure product 4a (2.08 g, 88percent). The same experimental procedure was adopted for the preparation of remaining title compounds (4b-l & 9) (Scheme 1 & 2, Table3).
Reference: [1] Combinatorial Chemistry and High Throughput Screening, 2015, vol. 18, # 9, p. 862 - 871
  • 29
  • [ 5394-63-8 ]
  • [ 6334-18-5 ]
  • [ 14205-39-1 ]
  • [ 138279-32-0 ]
  • [ 123853-39-4 ]
Reference: [1] Patent: WO2011/130852, 2011, A1, . Location in patent: Page/Page column 6
  • 30
  • [ 14205-39-1 ]
  • [ 123853-39-4 ]
Reference: [1] Patent: CN103242221, 2016, B,
  • 31
  • [ 14205-39-1 ]
  • [ 123853-39-4 ]
Reference: [1] Patent: CN103242221, 2016, B,
  • 32
  • [ 14205-39-1 ]
  • [ 123853-39-4 ]
Reference: [1] Patent: CN103242221, 2016, B,
  • 33
  • [ 14205-39-1 ]
  • [ 123853-39-4 ]
Reference: [1] Patent: CN103242221, 2016, B,
  • 34
  • [ 99-61-6 ]
  • [ 89226-49-3 ]
  • [ 14205-39-1 ]
  • [ 89226-50-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 9, p. 3787 - 3797
  • 35
  • [ 90120-00-6 ]
  • [ 14205-39-1 ]
  • [ 89226-50-6 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 9, p. 3787 - 3797
  • 36
  • [ 929212-20-4 ]
  • [ 14205-39-1 ]
  • [ 132866-11-6 ]
Reference: [1] Patent: WO2008/107797, 2008, A2, . Location in patent: Page/Page column 16
  • 37
  • [ 14205-39-1 ]
  • [ 869891-41-8 ]
Reference: [1] Patent: US2014/148454, 2014, A1,
[2] Patent: WO2014/82739, 2014, A1,
[3] Patent: WO2015/131080, 2015, A1,
[4] Patent: WO2005/110416, 2005, A2,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 14205-39-1 ]

Amino Acid Derivatives

Chemical Structure| 372-29-2

[ 372-29-2 ]

Ethyl 3-amino-4,4,4-trifluorobut-2-enoate

Similarity: 0.68

Chemical Structure| 582-33-2

[ 582-33-2 ]

Ethyl 3-aminobenzoate

Similarity: 0.58

Chemical Structure| 6296-99-7

[ 6296-99-7 ]

Diethyl 2-(aminomethylene)malonate

Similarity: 0.57

Chemical Structure| 1130155-48-4

[ 1130155-48-4 ]

(E)-4-(Dimethylamino)but-2-enoic acid xhydrochloride

Similarity: 0.53

Chemical Structure| 98548-81-3

[ 98548-81-3 ]

4-(Dimethylamino)but-2-enoic acid hydrochloride

Similarity: 0.53