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[ CAS No. 42042-68-2 ] {[proInfo.proName]}

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Chemical Structure| 42042-68-2
Chemical Structure| 42042-68-2
Structure of 42042-68-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 42042-68-2 ]

CAS No. :42042-68-2 MDL No. :MFCD00673140
Formula : C5H13NO Boiling Point : -
Linear Structure Formula :- InChI Key :DBKSSENEKWOVKL-UHFFFAOYSA-N
M.W : 103.16 Pubchem ID :9833937
Synonyms :

Calculated chemistry of [ 42042-68-2 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 30.11
TPSA : 32.26 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) : -7.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.61
Log Po/w (XLOGP3) : -0.17
Log Po/w (WLOGP) : -0.02
Log Po/w (MLOGP) : 0.23
Log Po/w (SILICOS-IT) : 0.2
Consensus Log Po/w : 0.37

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.11
Solubility : 80.4 mg/ml ; 0.779 mol/l
Class : Very soluble
Log S (Ali) : -0.05
Solubility : 91.5 mg/ml ; 0.887 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.29
Solubility : 5.3 mg/ml ; 0.0514 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 42042-68-2 ]

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 [ 42042-68-2 ]

* 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 [ 42042-68-2 ]
  • Downstream synthetic route of [ 42042-68-2 ]

[ 42042-68-2 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 37941-69-8 ]
  • [ 42042-68-2 ]
Reference: [1] Journal of Organic Chemistry, 1999, vol. 64, # 20, p. 7515 - 7522
[2] Organic Letters, 2001, vol. 3, # 23, p. 3765 - 3768
[3] Journal of Heterocyclic Chemistry, 2017, vol. 54, # 6, p. 3565 - 3573
[4] Patent: WO2011/131613, 2011, A1, . Location in patent: Page/Page column 14
[5] Patent: EP2377855, 2011, A1, . Location in patent: Page/Page column 7
  • 2
  • [ 67-56-1 ]
  • [ 13325-10-5 ]
  • [ 42042-68-2 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 23, p. 7368 - 7377
[2] Catalysis Letters, 2016, vol. 146, # 7, p. 1182 - 1193
  • 3
  • [ 174656-73-6 ]
  • [ 42042-68-2 ]
Reference: [1] Organic Mass Spectrometry, 1985, vol. 20, # 10, p. 595 - 599
[2] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 21, p. 6692 - 6704
[3] Patent: EP1400518, 2004, A1, . Location in patent: Page 22
[4] Journal of Medicinal Chemistry, 2013, vol. 56, # 14, p. 5819 - 5828
  • 4
  • [ 13325-10-5 ]
  • [ 109-94-4 ]
  • [ 42042-68-2 ]
YieldReaction ConditionsOperation in experiment
56%
Stage #1: for 18 h; Reflux; Inert atmosphere
Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran for 2 h; Reflux
Stage #3: With sodium hydroxide In tetrahydrofuran; water
To a stirred solution of 9 (4.31 g, 48.4 mmol) in EtOH (50 mL) was added ethylformate (5.86 mL, 75.5 mmol) and the mixture was stirred at reflux for 18 hrs under N2. The solution was evaporated under reduced pressure, and the crude product was used for the next step without further purification. The crude reaction mixture was dissolved in THF (25 mL) and added to a suspension of LiAlH4 (5.50 g, 145 mmol) in THF (50 mL) dropwise under a drying tube while stirring. The reaction mixture was brought to reflux and monitored by TLC (20percent EtOH/80percent CHC13) and JH NMR (CDC13). After 2 hours, the starting material was consumed, and 0 (4.16 mL) was added to the cooled reaction mixture, followed by 4 M NaOH (4.16 mL) and 0 (12.5 mL) while stirring vigorously. The precipitate was then removed by filtration, and the filtrate concentrated in vacuo. The residue was re-dissolved in CHCI3, dried over Na2S04, filtered and concentrated under reduced pressure to give 20 as a colorless oil (2.76 g, 56percent); JH NMR (CDC13) δ 3.74 (br, 2H), 3.57 (t, 2H), 2.62 (t, 2H), 2.43 (s, 3H), 1.50-1.75 (m, 4H).18
Reference: [1] Patent: WO2013/148230, 2013, A1, . Location in patent: Page/Page column 29; 30
  • 5
  • [ 928-51-8 ]
  • [ 74-89-5 ]
  • [ 42042-68-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 25, p. 4475 - 4480
[2] Chemical and Pharmaceutical Bulletin, 1978, vol. 26, # 12, p. 3891 - 3896
[3] J. Gen. Chem. USSR (Engl. Transl.), 1961, vol. 31, p. 2133 - 2139[4] Zhurnal Obshchei Khimii, 1961, vol. 31, p. 2289 - 2297
[5] Tetrahedron Letters, 1976, vol. No. 8, p. 593 - 596
  • 6
  • [ 67-63-0 ]
  • [ 42042-68-2 ]
Reference: [1] Patent: US6075010, 2000, A,
  • 7
  • [ 67-56-1 ]
  • [ 13325-10-5 ]
  • [ 123-75-1 ]
  • [ 42042-68-2 ]
  • [ 13330-96-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2002, vol. 41, # 18, p. 3476 - 3479
  • 8
  • [ 847260-15-5 ]
  • [ 42042-68-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 18, p. 7128 - 7137
  • 9
  • [ 6976-17-6 ]
  • [ 42042-68-2 ]
Reference: [1] Chemistry - A European Journal, 2014, vol. 20, # 1, p. 146 - 157
  • 10
  • [ 928-51-8 ]
  • [ 74-89-5 ]
  • [ 42042-68-2 ]
Reference: [1] DRP/DRBP Org.Chem.,
[2] DRP/DRBP Org.Chem.,
  • 11
  • [ 110-63-4 ]
  • [ 74-89-5 ]
  • [ 109-99-9 ]
  • [ 120-94-5 ]
  • [ 42042-68-2 ]
Reference: [1] Journal of Organic Chemistry, 1994, vol. 59, # 14, p. 3998 - 4000
[2] Journal of Organic Chemistry, 1994, vol. 59, # 14, p. 3998 - 4000
  • 12
  • [ 1191-99-7 ]
  • [ 74-89-5 ]
  • [ 42042-68-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1989, p. 1375 - 1380
  • 13
  • [ 67-56-1 ]
  • [ 13325-10-5 ]
  • [ 123-75-1 ]
  • [ 42042-68-2 ]
  • [ 13330-96-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2002, vol. 41, # 18, p. 3476 - 3479
  • 14
  • [ 50-00-0 ]
  • [ 42042-68-2 ]
  • [ 13330-96-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1989, p. 1375 - 1380
  • 15
  • [ 42042-68-2 ]
  • [ 24424-99-5 ]
  • [ 99207-32-6 ]
YieldReaction ConditionsOperation in experiment
84%
Stage #1: With triethylamine In methanol at 0℃; for 0.166667 h;
Stage #2: at 0 - 20℃; Inert atmosphere
A solution of 20 (2.76 g, 26.8 mmol) in TEA/MeOH (1 :7 v/v, 100 mL) was stirred at 0°C for 10 min. A solution of di- ferf-butyl dicarbonate (8.76 g, 40.2 mmol) in MeOH (20 mL) was added dropwise over 10 min. The mixture was stirred for 1 hr under N2 atmosphere. The temperature was allowed to gradually rise to room temperature, and the solution was stirred overnight. The solution was evaporated under reduced pressure, and the residue was dissolved in CH2CI2 and washed with deionized water. The organic layer was separated, dried over anhydrous Na2S04, filtered, and concentrated to give a colorless oil 21 that was used in the next step without further purification (4.54 g, 84percent); JH NMR (CDC13) δ 3.66 (t, 2H), 3.23 (t, 2H), 2.83 (s, 3H), 1.78 (br s, 1H), 1.51-1.60 (m, 4H), 1.44 (s, 9H).19
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 14, p. 5819 - 5828
[2] Patent: WO2013/148230, 2013, A1, . Location in patent: Page/Page column 30
[3] Tetrahedron Letters, 2006, vol. 47, # 43, p. 7551 - 7556
[4] Patent: US4975439, 1990, A,
  • 16
  • [ 42042-68-2 ]
  • [ 74651-77-7 ]
  • [ 99207-32-6 ]
YieldReaction ConditionsOperation in experiment
84% With triethylamine In 1,4-dioxane; ethyl acetate Preparation of N-BOC-N-Methyl-4-Aminobutanol (32)
To a 250 mL round bottom flask, charged with 3.00 g (28.5 mmol) of N-methyl-4-aminobutanol in 75 mL of dioxane, was added 5 mL of triethylamine (35.4 mmol) followed by 7.85 g (31.9 mmol) of BOC-ON, 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile.
The mixture was stirred at room temperature for 20 h and then concentrated via rotary evaporation.
The residue was chromatographed on silica gel, eluding first with 20percent ethyl acetate/hexane, then with 40percent ethyl acetate/hexane, and finally with 75percent ethyl/hexane.
The fractions containing product were combined and concentrated via rotary evaporation to afford 4.85 g of the product (32) as a near colorless oil (84percent): 1H-NMR (CDCl3) d 3.65 (2H, t), 3.23 (2H, t), 2.81 (3H, s), 1.67-1.45 (4H, m), and 1.42 (9H, s) ppm.
Reference: [1] Patent: US6172045, 2001, B2,
  • 17
  • [ 42042-68-2 ]
  • [ 99207-32-6 ]
Reference: [1] Patent: US4906643, 1990, A,
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